Ann K. Cady v. Matthew C. O'Malley

COURT OF APPEALS
DECISION NOTICE
DATED AND FILED This opinion is subject to further editing. If
published, the official version will appear in
the bound volume of the Official Reports.
January 23, 2026
A party may file with the Supreme Court a
Samuel A. Christensen petition to review an adverse decision by the
Clerk of Court of Appeals Court of Appeals. See WIS. STAT. § 808.10
and RULE 809.62.

Appeal No. 2025AP944 Cir. Ct. No. 2022CV155

STATE OF WISCONSIN IN COURT OF APPEALS
DISTRICT IV

ANN K. CADY, BETH L. CORNING, AND
CARON G. ROESLER,

PLAINTIFFS-RESPONDENTS,

V.

MATTHEW C. O’MALLEY,

DEFENDANT-APPELLANT.

APPEAL from an order of the circuit court for Sauk County:
WENDY J.N. KLICKO, Judge. Affirmed.

Before Graham, P.J., Kloppenburg, and Taylor, JJ.

Per curiam opinions may not be cited in any court of this state as precedent

or authority, except for the limited purposes specified in WIS. STAT. RULE 809.23(3).
No. 2025AP944

¶1 PER CURIAM. Matthew O’Malley appeals a circuit court order
that enforced a settlement agreement he made with his sisters regarding the
disposition of real estate and a family-owned corporation, and that dismissed this
litigation with prejudice pursuant to that agreement. We reject O’Malley’s
arguments and affirm the order of dismissal.

BACKGROUND

¶2 The plaintiffs, Ann Cady, Beth Corning, and Caron Roesler, and the
defendant, Matthew O’Malley, are siblings who shared ownership of real estate
and a family-owned corporation called Johnson-O’Malley, Inc. We refer to Cady,
Corning, and Roesler collectively as the “sisters”; to the three sisters and
O’Malley collectively as the “siblings”; and to Johnson-O’Malley, which is not a
party in this litigation, as the “corporation.”

¶3 When this lawsuit was initiated, each of the siblings owned an
undivided one-fourth interest in a parcel of residential real estate in the Village of
Lake Delton. Each of the siblings also owned one fourth of the shares of the
family corporation, meaning that the siblings were its sole shareholders. For its
part, the corporation owned a parcel of commercial real estate that was adjacent to
the residential parcel.

¶4 In or around 2021, some or all of the siblings decided that the
residential and commercial parcels should be sold, ideally to a single buyer. At
some point as they prepared for a sale, the communication between the siblings
broke down and O’Malley, who had been living in a house on the residential
property, refused to allow his sisters access to that property.

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The Pleadings

¶5 In April 2022, the sisters initiated this lawsuit and O’Malley
counterclaimed. As we discuss in more detail below, both sides generally agreed
that the real estate should be sold, and both sides asked for a judicially ordered
sale of one or both parcels pursuant to WIS. STAT. § 842.02(2) (2023-24).1
However, the sisters and O’Malley disagreed about how the proceeds of the sale
should be split between the siblings.

¶6 In their complaint, the sisters sought an injunction against O’Malley
that would grant the sisters access to the residential property and require O’Malley
to move out. They also sought an order for the judicial sale of the residential
property, which would be followed by a court-ordered equitable division of the
proceeds. According to the sisters’ request for relief, the distribution of sale
proceeds to O’Malley should be reduced based on “contributions” that the sisters
made to the residential real estate and reductions in the value of the real estate that
the sisters attributed to O’Malley, and also based on the theory of unjust
enrichment because O’Malley had been “living rent free” in the house on the
residential property.

¶7 In his answer, O’Malley denied that he owed any rent for the
residential property. He affirmatively alleged that any reduction in its value was
due to mismanagement by his sisters.

¶8 O’Malley also filed two counterclaims: one for unjust enrichment
and a second for a judicial sale. As for unjust enrichment, O’Malley alleged that

1
All references to the Wisconsin Statutes are to the 2023-24 version.

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No. 2025AP944

the sisters had been unjustly enriched by the efforts he had undertaken to manage
the residential property and the business on the commercial property, and he
sought the value of the services that he had provided for both properties. As for
the request for a judicial sale, O’Malley sought the sale of not only the residential
property but also the commercial property, and he took the position that the net
proceeds should be divided equally among the parties.

¶9 In their response to the counterclaims, the sisters denied that
O’Malley was entitled to any compensation. They affirmatively alleged that he
had taken insurance money for the residential property for his own personal use
and operated his own business out of the commercial property.

¶10 In February 2023, O’Malley’s first set of attorneys moved to
withdraw as counsel, citing a substantial breakdown in communication on the
substantive issues relating to the case. The circuit court did not enter an order
allowing the attorneys to withdraw until a month later, after the siblings had
entered into a settlement agreement but before they followed through on the
settlement by asking the court to dismiss the litigation. As discussed below,
O’Malley would go on to retain and then discharge two more sets of attorneys
during the course of the post-settlement phase of the litigation.

The Settlement

¶11 The siblings entered into a written settlement agreement on March 3,
2023. As we understand it, a significant impetus for the agreement was that there
had been an offer to purchase the residential and commercial real estate and some
or all of the siblings wanted to accept that offer. As we describe in greater detail
below, the written settlement agreement memorializes an agreement to sell the real
estate, to resolve the claims between the siblings, to distribute the proceeds of the

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No. 2025AP944

real estate sale, to transfer full ownership of the corporation to O’Malley, and to
dismiss this litigation. The siblings and the corporation were party to the
agreement, which was signed on March 3, 2023, by each of the siblings and by
one of the sisters, Ann Cady, on behalf of the corporation as its president. We
sometimes refer to the siblings and the corporation collectively as the “settling
parties.”

¶12 As for the real estate, the settlement agreement provided that both
parcels would be sold pursuant to the terms of the purchase offer, which was
incorporated into the agreement.2 The agreement further provided that, if the
closing did not occur “due to factors out of the control of the parties,” the
settlement agreement would be “null and void in its entirety.”

¶13 The settlement agreement resolved various disputes between the
siblings about who was owed money and who would be responsible for certain
corporate debts, and it also provided that O’Malley would assume sole ownership
of the corporation. For his part, O’Malley agreed that upon the closing of the real
estate sale, he would make a payment to Cady to pay off a personal loan, he would
resolve a specified judgment and certain debts that constituted liens on the real
estate, and he would be responsible for specified utility bills and certain credit card
and corporate debts. For the sisters’ part, they agreed to make a payment to
O’Malley, to pay certain utility and legal bills owed by the corporation, and to

2
The offer to purchase and its addendum were not included in the documents filed in the
record. There is no argument that the details of those documents are material to this appeal.

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surrender their roles, shares, and interests in the corporation to O’Malley, “thus
giving O’Malley 100% … ownership.”3

¶14 The settlement agreement also included a mutual release. Generally
speaking, the settling parties released each other from “any and all liability,
claims, counterclaims, damages, remedies, and causes of action, of any kind or
nature, … known or unknown, that existed or may have existed on or before the
date of this Agreement relating to the Subject Properties, the Corporation, or the
relationship between the Parties.” The release was qualified in that it did not “bar
any claim of the Corporation or [the sisters] against O’Malley for debts incurred
on behalf of the Corporation that are unknown to the Corporation or [the sisters],”
nor did it “bar any claim of the Corporation or O’Malley against [the sisters] for
debts incurred on behalf of the Corporation that are unknown to the Corporation or
O’Malley.”

¶15 Each of the settling parties expressly acknowledged that the written
settlement agreement constituted the “entire agreement and understanding between
the Parties.” They further acknowledged that no other party had “made any
statement, promise, representation, or warranty whatsoever … not contained
within this Agreement to induce [the settling party] to execute this Agreement,”
and that they had not executed the agreement “in reliance on anything not
contained” in the agreement.

¶16 Finally, the parties agreed to dismiss the lawsuit. The settlement
agreement provided: “Upon the complete execution of this Agreement, which

3
The settlement agreement also included provisions about how some personal property
would be distributed, but those provisions are not at issue here.

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No. 2025AP944

contemplates the closing of the Sale, the Parties shall then file a stipulation and
proposed order for dismissal of the Lawsuit with the Court.”

¶17 In mid-March 2023, the sisters’ attorney filed a letter to inform the
circuit court of the settlement. Counsel anticipated that a stipulation and order to
dismiss would be filed in May. However, no stipulation was forthcoming.
Meanwhile, as noted, after receiving the notice of settlement, the court allowed
O’Malley’s first set of attorneys to withdraw.

The Closing

¶18 The closing of the real estate transaction occurred on June 15, 2023,
with the two parcels of real estate selling for $1,000,000. Prior to the closing, the
parties worked with a closing agent to determine how the sale proceeds would be
divided. Each of the siblings would receive an equal share of the sale proceeds,
which would then be adjusted to account for the other payments and liabilities that
were resolved in the settlement agreement. For his part, O’Malley’s share of the
sale proceeds was adjusted upward to account for the settlement payment from the
sisters, and then downward to account for the loan payoff to Cady and the
payments of other debts and liabilities that O’Malley assumed in the settlement
agreement. A “closing statement” prepared by the closing agent memorialized the
dollar value of the distributions to each of the siblings, and the statement was
signed by each of the siblings and by Cady on behalf of the corporation.

¶19 The closing agent also prepared tax documents (Form 1099-S) for
the siblings and the corporation. The 1099s reflected that each of the siblings
received a quarter share of the sale proceeds (that is, $250,000) from the real estate
transactions and that the corporation received $0. Each of the siblings signed his
or her 1099, and Cady signed the 1099 for the corporation. When later questioned

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No. 2025AP944

at an evidentiary hearing, the closing agent testified that the direction on how to
distribute the proceeds came from meetings with the siblings, and the siblings’
agreement was evinced in the signed closing statement and the 1099s.

¶20 Following the closing and the distribution of the sale proceeds, the
sisters’ attorney prepared documents that would transfer the sisters’ shares of the
corporation to O’Malley and a stipulation that would dismiss the lawsuit.
O’Malley refused to accept the shares unless the sisters turned over corporate
documents and provided an “accounting” of the corporation’s finances. The
sisters provided documents, but O’Malley refused to accept them and refused to
sign the stipulation for dismissal.

The Motion to Enforce the Settlement Agreement

¶21 In July 2024, the sisters filed a motion asking the circuit court to
enforce the settlement agreement and dismiss the lawsuit. Although the motion
was styled as a “motion to dismiss,” it was not a motion based on a defense set
forth in WIS. STAT. § 802.06(2)(a), nor was it a motion for summary judgment.
Instead, it was effectively a motion seeking specific performance of the settlement
agreement, which would result in the dismissal of the lawsuit.

¶22 In the motion, the sisters represented that all of the terms of the
settlement agreement “have been satisfied or resolved except that” O’Malley had
“failed to accept” ownership of the corporation. The sisters represented that they
had attempted to transfer their shares to O’Malley, but he refused to accept them.
The sisters also represented that they had offered, in the alternative, to dissolve the
corporation. However, O’Malley had “not agreed to any proposed solution and
ha[d] not proposed any solution to dismiss the matter.”

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No. 2025AP944

¶23 O’Malley, who was at this time represented by a second set of
attorneys, filed a brief opposing dismissal. In that brief, O’Malley argued that the
sisters had failed to establish that two of the settlement agreement’s “conditions
[of] dismissal … ha[d] been met.” More specifically, he asserted, “the allocation
of liabilities for capital gains taxes on the sale proceeds” were “at variance from
the terms of the closing,” and the sisters had not provided “the books, accounts
and records of [the corporation] in up-to-date and merchantable form.” On the
latter point, O’Malley asserted, he was uncertain whether the documents that had
been turned over were complete, and he objected to “being asked to take delivery
of corporate records and indicia of ownership with no opportunity to verify their
completeness or accuracy.”

¶24 Additionally or perhaps in the alternative, O’Malley argued that the
terms of the settlement agreement were “so contingent” that the agreement “is of
questionable enforceability,” and also that the agreement was “not sufficiently
definite to be enforced.” O’Malley asserted that the parties should have included
additional terms in their agreement—“[t]he real estate closing and its subsequent
tax reporting should have been defined by precise terms” in the settlement
agreement, and “[t]he corporate assets should have been inspected, exceptions to
their suitability noted, and the problems cured,” presumably prior to executing the
settlement agreement.

¶25 A motion hearing was scheduled for September 2024. By that time,
O’Malley had discharged his second set of attorneys and was represented by a
third set. There is no transcript of the September 2024 hearing in the record, nor is
there any written order memorializing the results of that hearing. Based on later
representations by the circuit court and the siblings, we understand that O’Malley
raised concerns about the corporate documents he had received, and the sisters

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No. 2025AP944

offered to provide all documents in their possession. Consistent with that offer,
the court ordered the sisters to provide the documents and ordered O’Malley to
accept them, and it gave O’Malley 60 days to review the documents and to decide
whether he was maintaining his objection to dismissal of the lawsuit.

¶26 In December 2024, O’Malley’s third set of attorneys wrote to inform
the circuit court that O’Malley had reviewed the documents that had been
provided and continued to object to the lawsuit being dismissed. The letter stated
that, “[a]mong other things, the documents evidence that the [sisters] failed to
comply with material terms of the settlement agreement, and that those failures
may constitute grounds for invalidation or rescission of the parties’ agreement.”
The letter did not identify any particular term that the sisters failed to comply with,
nor did it identify any facts that would support invalidation or rescission of the
settlement agreement. The letter instead asked for a status conference to establish
“an appropriate scheduling order addressing additional discovery (to the extent the
court will permit it) and briefing.”

¶27 At the same time, O’Malley’s third set of attorneys moved to
withdraw from the case, citing “[f]undamental disagreements” that had “arisen
between [O’Malley] and his counsel such that continued representation would be
unreasonably difficult ….” Counsel’s motion asserted that “[w]ithdrawal may be
accomplished without material adverse effect to the defendant, the other parties to
this matter, or the [circuit] court.” The court did not at that time enter an order
allowing the third set of attorneys to withdraw.

¶28 Shortly thereafter, O’Malley filed a pro se motion and a pro se brief
opposing the pending motion to enforce the settlement agreement. In the pro se
motion, O’Malley cited his right to self-representation and asked the circuit court

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No. 2025AP944

to allow him to proceed pro se. In so doing, he “affirm[ed] that he underst[ood]
the responsibilities and obligations associated with self-representation, including
compliance with court rules and procedures.” O’Malley also asked the court to
“[a]dmit and consider” his pro se brief as a supplement to the brief that had been
previously filed by his second set of attorneys.

¶29 O’Malley’s supplemental brief was lengthy and at times difficult to
track, but we summarize its arguments as we best understand them. 4 According to
O’Malley, the settlement agreement was “invalid” because O’Malley had not
meaningfully participated in the negotiation; because the sisters and their attorney
unilaterally imposed certain terms; because the sisters’ attorney had previously
represented the corporation which created a “conflict of interest”; and because
O’Malley signed the agreement under “undue influence” or “duress.” Dismissal
pursuant to the settlement agreement was also “premature” because the agreement
contemplated that the lawsuit would not be dismissed until “execution” of the
agreement was “complete,” and that had not yet occurred because corporate
ownership had not been transferred to O’Malley.

¶30 O’Malley’s supplemental brief also asserted that he was unwilling to
accept the transfer of his sisters’ shares in the corporation because there were a
number of “unresolved issues” about how the corporation had been managed that

4
By attempting to summarize the arguments O’Malley made in his pro se motion and
supplemental brief in opposition, we do not mean to suggest that the circuit court was required to
consider them, given that O’Malley was represented by counsel when the motion and brief were
filed. See Johnson v. Johnson, 2016 WI App 60, ¶26, 371 Wis. 2d 388, 885 N.W.2d 603
(declining to consider a pro se motion filed by a litigant when the litigant was represented by
counsel at the time of the pro se filing); State v. Debra A.E., 188 Wis. 2d 111, 138, 523 N.W.2d
727 (1994) (addressing the concept of “hybrid” representation, and providing that an appellate
court may but need not consider pro se briefs filed by a represented appellant).

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No. 2025AP944

predated the 2023 settlement, including issues with corporate recordkeeping and
transparency. According to O’Malley, the corporate documents that had been
provided were inadequate and left lingering questions. Specifically, O’Malley
could not verify the sisters’ representation that the corporation had no assets after
the real estate was sold, nor could he verify whether it had additional undisclosed
liabilities that could offset the benefits of full ownership, rendering the settlement
agreement “inequitable.” Some of the “unresolved issues” that O’Malley
identified in his supplement were also the subject of O’Malley’s counterclaims,
and he argued that he potentially had other unpled claims such as breach of
fiduciary duty that he might wish to pursue against his sisters.

¶31 Additionally, O’Malley’s supplemental brief presented his concerns
about decisions that the sisters had purportedly made after the settlement
agreement was signed. One of these decisions had something to do with the
preparation of a schedule 5K-1 tax form which, O’Malley asserted, was not
consistent with the “property allocation values agreed to and executed at the
15 June 2023 closing.” Another decision concerned a purported quit claim of
corporate real estate to Sauk County. O’Malley asserted, among other things, that
he was entitled to certain disclosures, including a detailed list of all contracts that
the sisters entered into on behalf of the corporation since 2020.

¶32 The circuit court scheduled a telephone motion hearing to address
the motion to withdraw filed by O’Malley’s third set of attorneys. On January 7,
2025, the morning of the hearing, O’Malley filed a pro se motion that appeared to
reverse course on his request to represent himself—O’Malley instead asked the
court to “delay any subsequent hearings” to give time for “still missing corporate
records” to be provided and “to allow [O’Malley] time to secure replacement

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No. 2025AP944

counsel and to review corporate records necessary to properly respond to the
pending matters.”

¶33 The telephone motion hearing took place as scheduled on January 7,
2025. The circuit court acknowledged O’Malley’s request for additional time to
retain replacement counsel and review corporate records, but it expressed concern
about the length of time that the case had been pending and the fact that the
sisters’ attorney planned to leave his law firm after the end of the month. After
confirming that all of the corporate documents that had been provided to
O’Malley’s counsel had been turned over to O’Malley, the court granted counsel’s
motion to withdraw. The court agreed to postpone the evidentiary hearing on the
sisters’ pending motion until January 31, but no later, and stated that if O’Malley
wanted to be represented by counsel at the hearing, O’Malley would have to retain
counsel before the hearing date.

The Evidentiary Hearing

¶34 The evidentiary hearing proceeded as scheduled on January 31,
2025. O’Malley had not retained replacement counsel and represented himself.

¶35 At the start of hearing, the circuit court reviewed the posture of the
litigation between the siblings, and it identified what had been addressed and what
remained to be addressed in the litigation as follows. The sisters’ complaint and
O’Malley’s counterclaim had each sought judicial sale of the real estate, but that
relief was not something the court could order given that the real estate no longer
belonged to the settling parties. And, although O’Malley had also filed a
counterclaim for unjust enrichment, the counterclaim had been resolved through
the settlement agreement. Specifically, the siblings had agreed that the
disbursements from the real estate sale would “resolve” their competing claims

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No. 2025AP944

“about the other being unjustly enriched.” Accordingly, O’Malley’s counterclaim
need not be further addressed, assuming that the settlement agreement was
enforceable. Under these circumstances, there were no remaining claims or
counterclaims in the lawsuit left to adjudicate, and the focus of the evidentiary
hearing would be on whether the court should order enforcement of the settlement
agreement, which would result in the dismissal of the lawsuit.

¶36 When asked whether he agreed with the circuit court’s summary of
the remaining issues in the litigation, O’Malley again brought up concerns about
missing corporate documents, and the court questioned the sisters’ attorney about
whether all known corporate documents had been provided to O’Malley. Counsel
represented that, based on his conversations with the sisters, all known corporate
records in their possession had been turned over, and O’Malley responded that he
had not received documents such as “corporate minutes from many major
decisions that were made after the settlement agreement.” Counsel maintained
that the existing records had been turned over, and suggested that O’Malley was
raising a different question about whether “corporate records weren’t properly
kept.” Based on this discussion, the court stated that “there isn’t anything more
for the court to order at this time.”

¶37 The closing agent testified at the hearing, and her testimony was
consistent with the facts set forth above: all four siblings had agreed to the division
of sale proceeds that was represented in the closing statement; the proceeds were
disbursed consistent with that statement; and the 1099 tax forms accurately
reflected that all of the proceeds were distributed to the siblings and none to the
corporation. The closing agent further testified that the siblings all agreed that
Cady should sign the paperwork on the corporation’s behalf.

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No. 2025AP944

¶38 O’Malley also testified at the hearing. Although the circuit court
gave some latitude to O’Malley to present his case, the court also sustained
objections and redirected O’Malley’s testimony when it determined that O’Malley
was veering into topics that were irrelevant to the enforceability of the settlement
agreement, which was the only remaining issue in the litigation. We describe
O’Malley’s testimony in some detail, as it provides helpful context to his
arguments on appeal.

¶39 During his testimony, O’Malley made a number of admissions about
the circumstances surrounding the negotiation and execution of the settlement
agreement. Among other things, O’Malley admitted that the siblings had
discussed dissolving the corporation as part of the settlement, but that he had
specifically asked that the ownership of the corporation be transferred to him
instead. He also admitted that he signed the settlement agreement, the closing
paperwork, and his 1099; that the real estate had been sold and the proceeds had
been disbursed; and that the disbursement of sale proceeds and 1099s were
consistent with the settlement agreement. In O’Malley’s view, the transfer of
ownership was the only portion of the settlement agreement that had not been
completed.

¶40 O’Malley further testified that he believed that he was the sole
owner of the corporation pursuant to the settlement agreement. However, in his
view, ownership “hasn’t been properly transferred” because his sisters had not
provided a full accounting of its assets and liabilities. When asked to identify a
provision in the agreement that required specific documentation to be provided,
O’Malley pointed to the provision that stated: “[The sisters] agree at Closing to
surrender any and all Johnson-O’Malley roles, shares and interests over to
O’Malley, thus giving O’Malley 100% … ownership.” As we best understand

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No. 2025AP944

O’Malley’s testimony, the point he was attempting to convey was that his 100%
ownership included ownership of all corporate records and that, “according to
Wisconsin business law,” the transfer is not complete until records are provided.

¶41 During his testimony, O’Malley also asserted that he had not wanted
to agree to the terms of the settlement agreement and was under “undue influence”
to sign it. More specifically, he testified that he had wanted the property to be
partitioned rather than sold, but he “was told that if [he] didn’t sign the agreement”
the corporation might lose its liquor license, “the buyer might walk,” the lost value
“would come out of … [his] ownership proceeds,” and the house on the residential
property would likely be condemned. When asked how those facts amounted to
undue influence, O’Malley testified that the situation “created a sense of urgency
that wouldn’t be there otherwise.”

¶42 O’Malley also testified that, in his view, it was “highly
inappropriate” for the corporation to be included as a party to the settlement
agreement. According to O’Malley, the corporation had not been included until
the sisters’ attorney added it as a party to the settlement agreement at the “last
minute.” O’Malley asserted that the attorney must have been representing the
corporation as well as his sisters during the settlement negotiations, and that the
attorney continued to represent the corporation after the closing occurred.

¶43 In addition, O’Malley’s testimony touched on his concerns about
poor corporate recordkeeping practices over a period of 20 years, and he asserted
that the corporation might have liabilities that he was unaware of for which he
would be responsible.

¶44 Finally, O’Malley also vaguely alluded to events that, he suggested,
had occurred after the closing. Specifically, he testified, “my understanding is

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No. 2025AP944

they [the sisters, presumably] made a huge shift for their tax benefits that greatly
harmed me,” and “my understanding is they flipped it and suddenly there was
$700,000 put on the corporation that wasn’t there.” O’Malley did not introduce
evidence to support these assertions.

¶45 The circuit court determined that the siblings had voluntarily entered
into the settlement agreement, and that it was enforceable. Therefore, the court
ordered specific performance of the remaining provisions of the agreement—
namely, that all shares of the corporation belonged to O’Malley as of the date of
the closing, and the dismissal of the lawsuit.

¶46 The circuit court made the following factual and legal
determinations in support of its ruling. The settlement agreement was signed by
all of the siblings and by Cady on behalf of the corporation. The agreement
contemplated a full resolution of all of the issues in the lawsuit, including the
manner in which the sale proceeds would be divided after the closing. All of the
events contemplated by the agreement had occurred. The settling parties had all
agreed that the numbers in the closing statement were correct, and the proceeds
were disbursed according to that statement. The parties also signed the 1099s
consistent with their prior agreement.

¶47 The circuit court also determined that the facts that O’Malley
testified to regarding a “sense of urgency” did not amount to undue influence or
duress. As the court explained, “urgency certainly plays a part in all kinds of
business dealings,” especially in real estate transactions. However, it “is not a
threat” to discuss the “potential outcomes” of not reaching an agreement—it is
instead a natural part of the negotiation process, which includes “providing
information” so that the parties can make “a reasoned decision … about whether

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to go forward or not.” If O’Malley had questions about corporate recordkeeping
or other matters, he should have resolved his questions before signing the
settlement agreement.

¶48 The circuit court entered an order that dismissed all claims and
counterclaims with prejudice and ordered that all “roles, shares, and interests [in
Johnson O’Malley, Inc.] are transferred from [the sisters] to [O’Malley], giving
[O’Malley] 100% ownership effective June 15, 2023.” O’Malley appeals.5

5
The briefs and appendices filed in this appeal violate various provisions of the rules of
appellate procedure found in WIS. STAT. ch. 809.

First, the brief and appendix that the sisters filed and the reply brief and appendices that
O’Malley filed do not comply with WIS. STAT. RULE 809.19(8)(bm), which addresses the
pagination of appellate briefs and appendices. See RULE 809.19(8)(bm) (providing that, when
paginating briefs, parties should use “Arabic numerals with sequential numbering starting at ‘1’
on the cover”). This rule was amended to its current form in 2021, see S. CT. ORDER 20-07, 2021
WI 37, 397 Wis. 2d xiii, and the reason for the amendment is that briefs are now electronically
filed in PDF format, and are electronically stamped with page numbers when they are accepted
for efiling. The pagination requirements ensure that the numbers on each page of a brief “will
match … the page header applied by the eFiling system, avoiding the confusion of having two
different page numbers” on every page of a brief. Supreme Court Note, 2021, RULE 809.19.

Second, O’Malley’s appendices also include some documents that were not filed during
the circuit court proceedings and are not included in the record on appeal. We disregard these
documents because our appellate review is limited to the record on appeal, which contains only
those documents that were presented during the circuit court proceedings. See State ex rel. Wolf
v. Town of Lisbon, 75 Wis. 2d 152, 155-56, 248 N.W.2d 450 (1977).

Third, although WIS. STAT. RULE 809.19(1)(d) and (e) require appellate briefs to contain
appropriate references to the record and citation of supporting legal authorities, O’Malley’s
briefing contains a number of factual assertions that are not paired with any reference or citation
to any portion of the record and a number of assertions about the law that are not paired with
citations to legal authority. It is within our discretion to disregard such factual and legal
assertions as unsupported. See State v. Pettit, 171 Wis. 2d 627, 646-47, 492 N.W.2d 633 (Ct.
App. 1992) (a court need not consider arguments that are unsupported by legal citations or are
otherwise undeveloped).

Finally, and most troublingly, O’Malley’s briefs also include false legal citations.
Specifically, some of the citations in his briefs are to legal authorities that do not exist, and other
citations are to legal authorities that exist but are wholly unrelated to the proposition for which
they are cited. The inclusion of false legal citations in O’Malley’s briefing violates WIS. STAT.
(continued)

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No. 2025AP944

DISCUSSION

¶49 There is no dispute that, during the course of this litigation,
O’Malley signed a settlement agreement that expressly provided that it was
intended to be a full settlement of all claims that were or could have been brought
in the litigation. The agreement, which was not contingent on any future event
except the closing of the real estate sale, was made in writing and subscribed by
each party; therefore, the statutory requirements for a binding and enforceable
settlement agreement are satisfied. See WIS. STAT. § 807.05; see also Affordable
Erecting, Inc. v. Neosho Trompler, Inc., 2006 WI 67, ¶¶22-24, 28, 291 Wis. 2d
259, 715 N.W.2d 620 (interpreting § 807.05).6

¶50 On appeal, O’Malley makes a number of arguments about why the
circuit court should not have enforced the settlement agreement, which called for
the dismissal of the lawsuit. His arguments are at times difficult to parse, only
some of them were raised during the circuit court proceedings, and many are not

RULE 809.19(1)(e) and (4)(b). The sisters pointed out these false citations in their respondents’
brief, but O’Malley did not acknowledge the error in his reply brief and instead continued to use
the same false citations. This is a significant violation of court rules; accordingly, we considered
whether, on our own motion, to order O’Malley to show cause why he should not be sanctioned
for the false citations pursuant to RULE 809.19(2), which provides broad authority to issue
sanctions for a failure to comply with this court’s rules. In the end, we decline to issue such an
order in favor of a prompt resolution of this appeal. But we caution O’Malley not to repeat this
violation in any future filings in this or any court. We offer an additional note of caution—if the
root of the problem is that O’Malley used generative AI for legal research and trusted it to
provide accurate results, he should be aware that there are many reported instances in which
generative AI has hallucinated nonexistent cases and misreported the holdings of existing cases.
6
WISCONSIN STAT. § 807.05 provides: “No agreement, stipulation, or consent between
the parties or their attorneys, in respect to the proceedings in an action or special proceeding shall
be binding unless made in court … and entered in the minutes or recorded by the reporter, or
made in writing and subscribed by the party to be bound thereby ….” Whether a settlement
agreement is enforceable under this statute is a question of law that we review de novo. Waite v.
Easton-White Creek Lions, Inc., 2006 WI App 19, ¶5, 289 Wis. 2d 100, 709 N.W.2d 88 (2005).

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No. 2025AP944

supported by citations to the record or legal authority. We now consider
O’Malley’s arguments as best as we understand them.

¶51 We begin with O’Malley’s arguments about purportedly unfilled
“conditions precedent” to the dismissal of the lawsuit. Whether the conditions
precedent to the enforcement of a settlement agreement have been fulfilled
involves both questions of law (what the agreement requires) and questions of fact
(whether those things occurred as the agreement requires). Schlosser v. Allis-
Chalmers Corp., 86 Wis. 2d 226, 244, 271 N.W.2d 879 (1978) (the meaning of an
unambiguous contract is a question of law); Smith Realty Co. v. Zimmerman, 75
Wis. 2d 11, 17, 248 N.W.2d 472 (1977) (whether a party’s activities constitute
performance of its obligations under a contract may present a question of fact).

¶52 O’Malley argues that the circuit court erred by dismissing the
lawsuit pursuant to the settlement agreement without regard to whether the
conditions precedent to dismissal had been satisfied. Specifically, O’Malley
contends, those conditions were “the proper transfer of corporate ownership” and
“an honest allocation of the sale proceeds,” which, O’Malley asserts, “did not
occur.” “[A]t minimum,” O’Malley argues, the court should have “held an
evidentiary hearing on whether the settlement conditions were met” but the court
“instead … enforced the [settlement] agreement without inquiry.”

¶53 This argument is ahistorical—as noted, the circuit court did hold an
evidentiary hearing, and during the hearing it gave explicit consideration to
whether everything that the agreement contemplated happening prior to dismissal
had occurred. The court found that everything the agreement contemplated had
indeed occurred, and O’Malley does not persuade us that the court erred with
respect to any determination on these points.

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¶54 To illustrate, regarding the first alleged condition precedent—the
transfer of corporate ownership—the circuit court found that the sisters had
attempted to transfer their shares to O’Malley. The court also implicitly found that
O’Malley did not have any valid reason to refuse to accept their shares. Therefore,
the court ordered that the corporation belonged to O’Malley as of the date of the
closing, thus fulfilling that aspect of the settlement agreement.

¶55 Although O’Malley continues to argue that no proper transfer of
corporate ownership occurred, his argument is unsupportable. The argument
appears to be based on his assertion that the sisters have not given him certain
corporate documents that may or may not exist. However, O’Malley does not
point to any provision of the settlement agreement that contemplated an exchange
of documents. That omission is telling—although the court ordered the sisters to
produce the records in their possession after they offered to do so, there was
nothing in the settlement agreement that required any particular records or
documents to be provided. Therefore, there was no unfulfilled condition
precedent regarding the transfer of corporate ownership.7

7
Indeed, rather than arguing on appeal that the settlement agreement required the
transfer of any specific documentation, O’Malley points to the statutory provisions in WIS. STAT.
§§ 180.1602-1604 that govern a shareholder’s right to inspect corporate records and a
corporation’s statutory responsibilities with respect to a shareholder’s written notice for an
inspection of corporate records. There are several independent problems with any argument
O’Malley might be making about these statutes. First, O’Malley did not make any argument
based on §§ 180.1602-1604 during the circuit court proceedings. Second, he does not specifically
identify any notice that he sent to the corporation’s registered agent, as required by
§ 180.1602(2)(c) and WIS. STAT. § 180.1150(1)(c). Third, § 180.1604 addresses a shareholder’s
recourse against a corporation that refuses to allow inspection; therefore, any claim under that
statute would be against the corporation, not against his sisters. As O’Malley acknowledges
elsewhere in his brief, the corporation is not a party to this litigation. Finally, even if O’Malley
had shown a violation of §§ 180.1602-1604, he does not point to anything in the settlement
agreement establishing that compliance with these statutes was a prerequisite to transferring
ownership of the corporation.

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No. 2025AP944

¶56 Regarding the second alleged condition precedent, the allocation of
sale proceeds, the circuit court found that the proceeds were disbursed in
accordance with the settlement agreement and the closing statement, which had
been approved by O’Malley. O’Malley does not argue that this finding is clearly
erroneous, nor does he dispute that he actually received his share of the proceeds,
as reflected in the closing statement. Therefore, to the extent that the proper
disbursement of sale proceeds was a condition precedent of dismissal, that aspect
of the settlement agreement was also fulfilled.

¶57 O’Malley makes arguments about the sale proceeds on appeal, but
his concern does not appear to be about how the net proceeds were disbursed (that
is, all to the siblings and none to the corporation). Instead, as best as we
understand it, his concern appears to be that, following the closing, a portion of the
lump sum payment for the real estate may have been attributed to the commercial
parcel that had been owned by the corporation. O’Malley contends that this
attribution of value has tax consequences and his concern may or may not be valid
as an accounting and tax matter, but it is wholly irrelevant to the issue here. The
issue is whether there were any remaining conditions that had to be fulfilled before
the litigation was dismissed pursuant to the settlement agreement, and there were
no terms in that agreement that addressed the tax consequences of the real estate
transaction. Nor were there any terms that addressed how the payment should be
allocated between the two parcels that were included in the real estate sale.
Therefore, O’Malley has not identified an unfulfilled condition precedent to
dismissal pursuant to the settlement agreement.

¶58 We now turn to O’Malley’s numerous arguments about the sisters’
pre-settlement actions with respect to managing the corporation. In continuing to
advance these arguments, O’Malley does not come to grips with the fact that he

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No. 2025AP944

signed a settlement agreement that resolved all of the claims he had raised in the
litigation and that also included a mutual release. Accordingly, the sisters’ pre-
settlement actions are no longer relevant for purposes of this litigation unless there
is some reason that the settlement agreement is unenforceable.

¶59 O’Malley makes several arguments about why the settlement
agreement is unenforceable which we now consider and reject.

¶60 To the extent that O’Malley renews an argument about undue
influence or duress, the circuit court determined that the facts O’Malley testified to
did not amount to either. O’Malley does not develop an argument as to why that
determination is erroneous. He does make some assertions about being under
“pressure from multiple directions,” about the quality of representation he
received from his attorney during settlement negotiations, and about the sisters’
attorney’s “last-minute” insistence that the corporation be included in the
settlement agreement and its mutual release, but he does not attempt to pair those
arguments with the elements of either legal doctrine.8

¶61 Instead, O’Malley makes new arguments about alleged fraudulent
inducement or alleged material breaches of the settlement agreement. Although

8
Undue influence is a legal theory that is typically used as a basis for objecting to a will,
and has no apparent relevance here. See Kehrbert v. Pribnow, 46 Wis. 2d 205, 208-09, 174
N.W.2d 256 (1970) (discussing the elements of undue influence, which are susceptibility,
opportunity, disposition, and the achievement of a coveted result).

Economic duress can be a defense to the enforcement of a contract, but a party alleging
economic duress must prove that the party was the victim of a wrongful or unlawful act; the act or
threat deprived the party of the party’s unfettered will; and as a result, the party was compelled to
make a disproportionate exchange of values or give something up for nothing. Wurtz v.
Fleischman, 97 Wis. 2d 100, 109, 293 N.W.2d 155 (1980). O’Malley has not shown that any of
these elements were satisfied here.

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No. 2025AP944

O’Malley discussed the sisters’ pre- and post-closing conduct in detail in his
circuit court filings, he did not develop any theory based on fraudulent inducement
or material breach in the arguments he made in the circuit court. We could
disregard O’Malley’s argument on that basis,9 but we choose to further address
those arguments for completeness.

¶62 Beginning with fraudulent inducement, for O’Malley’s argument to
have any merit, there would have to be facts showing that the sisters engaged in
fraudulent conduct before the settlement agreement was executed. Kaloti
Enterprises, Inc. v. Kellogg Sales Co., 2005 WI 111, ¶42, 283 Wis. 2d 555, 699
N.W.2d 205 (“[t]o invoke this narrow fraud in the inducement exception,” the
misrepresentation must occur “before the contract was formed”). Here, there were
no facts identified in O’Malley’s circuit court filings or that were adduced at the
hearing that would support an argument that fraudulent conduct occurred before
the settlement agreement was executed. To be sure, O’Malley’s pro se
supplemental brief in opposition to dismissal asserted that there were “serious
concerns of potential fraud” with respect to post-closing documentation that
allocated the purchase price between the two parcels of real estate, but O’Malley
fails to explain how post-closing conduct that occurred after the settlement
agreement was signed could have induced him to sign the agreement.

¶63 As for O’Malley’s argument that the sisters materially breached
terms in the settlement agreement, there are several significant problems. Most

9
See Green v. Hahn, 2004 WI App 214, ¶21, 277 Wis. 2d 473, 689 N.W.2d 657
(“Except in rare circumstances that are not present here, we will not address an issue that an
appellant raises for the first time on appeal, because doing so undermines judicial economy and
creates an incentive for parties to build in error in order to have an adverse outcome in the trial
court overturned on appeal.”).

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No. 2025AP944

notably, O’Malley has not identified any conduct by the sisters that would
constitute a material breach of any term in the settlement agreement. As
mentioned, the agreement did not require the sisters to provide any particular
documents, and did not address how the purchase price would be allocated
between the parcels of real estate. To the extent that O’Malley or the corporation
could potentially have a legal claim against someone or something with respect to
any pre- or post-closing actions, including how the settlement proceeds were
reported for tax purposes, he does not identify any legal theory under which that
potential claim would prevent the settlement agreement from being enforced.10

¶64 Separately, O’Malley also makes some arguments about the
propriety of the role that the attorney who represented his sisters played in the
litigation. Specifically, O’Malley asserts that the attorney was engaged in “dual
representation” because he was “speaking for the corporation” as well as his
sisters during the settlement negotiations, and that the attorney continued to
represent the corporation in the litigation that occurred after the settlement
agreement was signed. O’Malley argues that the attorney “claimed to represent a
company they no longer owned—against the interests of its sole shareholder,” and
he suggests that the circuit court erred by not requiring “proof of [the attorney’s]
authority to represent the corporation post-closing.”

¶65 These arguments fail because, among other things, they are not
supported by the record. Most notably, O’Malley does not identify any occasion

10
In his appellate briefing, O’Malley makes a more general argument about “post-
signing misconduct” which, he asserts, could prevent the settlement agreement from being
enforced. However, as legal authority for this proposition, he includes a citation to a purported
Wisconsin Court of Appeals case that does not exist. This is consistent with other false case
citations that are scattered throughout his briefs, which we disregard.

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No. 2025AP944

during this litigation in which the attorney who represented the sisters purported to
represent or speak for the corporation. O’Malley asks us to infer that the attorney
must have been representing the corporation’s interests, rather than the sisters’
interests, because the attorney insisted that the corporation be included as a party
to the settlement agreement and because the attorney argued against some of the
requests that O’Malley made in the circuit court, but that inference does not hold
up. The sisters, who had been corporate shareholders and had participated in its
management, would have had good reasons to want the corporation to be included
in the settlement agreement so that O’Malley, who would control the corporation
after the closing, would be precluded from bringing claims against them on the
corporation’s behalf. And the sisters would also have had a personal stake in
wanting the litigation to be dismissed. The fact that the sisters’ attorney pushed
for these positions in and out of court is not proof that the attorney was
representing the corporation rather than or in addition to the sisters in this
litigation.11

¶66 Finally, O’Malley makes a series of due process arguments about
how his right to be heard was violated by the “truncated” proceedings held by the
circuit court. Specifically, O’Malley takes issue with the fact that the court limited
the time devoted to the evidentiary hearing, sustained a number of objections to
the relevance of evidence he wanted to offer, and dismissed the case even though,

11
Conversely, O’Malley argues that if the attorney did not represent the corporation
during the settlement negotiations, that could create a different problem, in that the corporation
would be bound to an agreement it entered without its own counsel. O’Malley does not cite any
legal authority to support his assertion that this creates a problem, and we see no problem under
these facts. As noted, all of the shareholders of the corporation were parties to the settlement
agreement, and O’Malley fails to explain why the shareholders could not collectively reach an
agreement to which the corporation would also be bound.

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No. 2025AP944

O’Malley asserts, a number of O’Malley’s motions remained “unresolved.” None
of these arguments have merit.

¶67 O’Malley’s assertion that he had pending motions that were not
resolved prior to dismissal is not borne out in the record.12 O’Malley may mean to
argue that the circuit court dismissed the litigation without addressing every
argument that O’Malley wanted the court to address, but he has not identified any
reason that the court was required to address these arguments, given the court’s
determination that there was an enforceable settlement agreement that called for
dismissal of the litigation. It was also within the court’s discretion to exclude
irrelevant evidence that went beyond the scope of the hearing, and we agree with
the court’s view on the proper scope of the hearing. The additional evidence that
O’Malley wanted to offer may have been relevant to a number of potential claims
that O’Malley would have liked to bring against his sisters, but it was not relevant
to the narrow issue before the court, which was whether the settlement agreement
should be enforced. Finally, regarding the two-hour time slot that the court

12
The record reflects that O’Malley filed three motions, the first two on December 16,
2024, and the third on the morning of January 7, 2025. The December 2024 motions asked the
circuit court to allow him to proceed pro se, to consider his pro se brief, and to seal certain
documents that he had filed, and the court did that. O’Malley’s January 2025 motion asked the
court to “delay any subsequent hearings … for 60 days following receipt of still missing
corporate records to allow [O’Malley] time to secure replacement counsel and to review
corporate records,” and the court gave its reasons for denying that motion during the hearing that
took place that same day.

O’Malley’s appellate briefing makes references to “motions to compel” that O’Malley
says he filed during the circuit court proceedings, but there is nothing in the record that supports
O’Malley’s assertion that he filed a motion to compel. O’Malley may be referring to the pro se
motions he filed in December 2024 and in January 2025 that we addressed in the preceding
paragraph; if so, none of these documents contained any motion to compel. Likewise, although
O’Malley asserts that his January 2025 motion “condition[ed] withdrawal” of his third set of
attorneys on his sisters’ “production of missing corporate records and time for review,” the
motion did no such thing.

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No. 2025AP944

devoted to the evidentiary hearing, it is within a circuit court’s discretion to
schedule proceedings in a manner that balances the need of any one case against
the needs of others. See Hefty v. Strickhouser, 2008 WI 96, ¶31, 312 Wis. 2d
530, 752 N.W.2d 820 (“circuit courts have discretion to control their dockets”).
Here, we are not persuaded that the court erred by allotting two hours for the
hearing, especially given the narrow issue that was before the court.13

¶68 For all of the above reasons, we conclude that the circuit court did
not err in enforcing the settlement agreement and dismissing this litigation with
prejudice pursuant to that agreement.

By the Court.—Order affirmed.

This opinion will not be published. See WIS. STAT.
RULE 809.23(1)(b)5.

13
To the extent that O’Malley makes any additional arguments in his appellate briefs
that we have not explicitly addressed here, we reject those arguments as undeveloped,
unsupported, or unpersuasive. Pettit, 171 Wis. 2d 627, 646-47.

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