Timothy Upchurch v. TIMOTHY M. O’BRIEN, MARGARET M. O’BRIEN, and STEVEN M. LUCARELI

In the
United States Court of Appeals
for the Seventh Circuit
____________________
No. 22-2541
TIMOTHY UPCHURCH,
Plaintiff-Appellant,
v.
TIMOTHY M. O’BRIEN, MARGARET M. O’BRIEN,
and STEVEN M. LUCARELI,
Defendants-Appellees.
____________________
Appeal from the United States District Court
for the Western District of Wisconsin.
No. 19-cv-165-wmc — William M. Conley, Judge.
____________________
SUBMITTED MARCH 29, 2023 — DECIDED AUGUST 6, 2024
____________________
Before SYKES, Chief Judge, and ROVNER and BRENNAN,
Circuit Judges.
SYKES, Chief Judge. For years Timothy Upchurch waged a
relentless and disturbing campaign of harassment against his
neighbors, Timothy and Margaret O’Brien, in a dispute over
a claimed easement across their property for access to the
shores of Catfish Lake. The local sheriff’s office eventually
stepped in, and Upchurch was convicted of disorderly

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2 No. 22-2541
conduct, criminal damage to property, and theft stemming
from his trespass on the O’Briens’ property and theft of their
security camera. Upchurch retaliated with this suit against the
O’Briens, their lawyer, the local district attorney, and three
sheriff’s deputies seeking damages under the Racketeer Influ-
enced and Corrupt Organizations Act (“RICO”) for alleged
interference with his claimed easement.
The suit was utterly frivolous from its inception. Up-
church does not own an easement over the O’Briens’ prop-
erty, and the RICO claim was baseless and vindictive, filed
only for the purpose of harassment. After about a year of liti-
gation and facing sanctions motions under Rules 11 and 37 of
the Federal Rules of Civil Procedure, Upchurch dropped the
case. The district judge awarded sanctions and ordered Up-
church and his attorney, Timothy Provis, to pay the defend-
ants’ costs and attorney’s fees.
Upchurch appealed, claiming that the judge was required
to hold a hearing before imposing sanctions. The appeal is un-
timely; we dismiss it for lack of jurisdiction. The appeal is also
thoroughly frivolous, so we grant the defendants’ motion for
sanctions under Rule 38 of the Federal Rules of Appellate Pro-
cedure.
I. Background
For more than 30 years, Timothy O’Brien and his wife,
Margaret, owned Everett Resort on Catfish Lake in Eagle
River, Wisconsin. For many years Timothy Upchurch, who
lived in a neighboring cottage, insisted that he had an ease-
ment in his deed that guaranteed access to the lake over the
resort property. The O’Briens disputed his claim; they in-
stalled “No Trespassing” signs, surveillance cameras, and

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No. 22-2541 3
other security measures to deter him from trespassing on their
property.
Upchurch responded to these measures with a persistent
and troubling campaign of harassment against the O’Briens.
Starting in 2003, he sent hostile and expletive-laden notes and
letters to the O’Briens and Steven Lucareli, their lawyer. In
2012, the letters had become more frequent and aggressive,
prompting the Vilas County Sheriff’s Office to warn Up-
church that his conduct amounted to stalking and that he
would be arrested if it continued.
About a year later, a security camera caught Upchurch
trespassing on resort property and stealing a second security
camera the O’Briens had installed after Upchurch twice used
a chainsaw to cut down a fence at the resort. The O’Briens re-
ported the trespass and theft to law enforcement, and Up-
church was charged with stealing the security camera. He
pleaded no contest and was convicted of theft.
Undeterred, Upchurch was soon arrested for stalking the
O’Briens. He was charged with disorderly conduct and crim-
inal damage to property. He again pleaded no contest and
was convicted. In 2015 the O’Briens applied for a restraining
order against Upchurch. The petition was resolved with an
agreement among the parties that Upchurch could not go
within 200 yards of the O’Briens or their property.
With this agreement in place, Upchurch focused his atten-
tion on Lucareli, the O’Briens’ lawyer. In 2017 he filed griev-
ances against the attorney with the Wisconsin Supreme
Court’s Office of Lawyer Regulation. He asserted that Lu-
careli was an “absolute menace to our society” and that he,

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4 No. 22-2541
along with the O’Briens, “should be prosecuted and sent to
prison.”
In 2018 the O’Briens sold Everett Resort. Upchurch still
did not relent. Represented by Attorney Timothy Provis, he
filed suit in federal court against the O’Briens, Lucareli, the
Vilas County District Attorney, and three Vilas County sher-
iff’s deputies. The complaint alleged that Upchurch had “an
easement in his deed” giving him access to Catfish Lake over
the Everett Resort property, and that the defendants had en-
gaged in an illegal racketeering enterprise and committed a
pattern of racketeering acts—specifically, extortion and ob-
struction of justice—with the purpose of interfering with his
easement, all in violation of RICO, 18 U.S.C. §§ 1962(c),
1964(c). The complaint sought triple damages, punitive dam-
ages, attorney’s fees, and costs.
The complaint’s foundational factual allegation—that Up-
church owned a deed with a lake-access easement over the
resort property—was false. Though he lived in a cottage next
door, he was not the title holder and owned neither a deed to
the property nor an easement for lake access across Everett
Resort.
The different groups of defendants filed motions to dis-
miss, and the O’Briens also moved for sanctions under Rule
11. The latter motion highlighted Upchurch’s disturbing cam-
paign of harassment and the complete absence of any good-
faith basis in fact or law for the RICO claim.
Provis’s response on his client’s behalf included only his
own declaration conceding that Upchurch did not in fact own
a deed or easement, as the suit had claimed. Provis instead
asserted that the relevant easement was “in the name of the

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No. 22-2541 5
Weiland family trust” and that Marvin Weiland—the father
of Upchurch’s wife—would “sign an affidavit” at “an appro-
priate time” confirming that Upchurch was entitled to use the
easement. As for the sanctions motion, Provis offered mostly
non-responsive retorts and concluded with the grandiose as-
sertion that “[t]his case is about a powerful corporation im-
posing its will on ordinary folks” and that if Provis “had time
to waste[,] he would ask for sanctions against the O’Briens.”
Discovery proceeded while the dismissal and sanctions
motions were pending. When Provis neither served initial
disclosures nor responded to defense discovery requests, the
O’Briens filed a motion to compel. In an order granting the
motion, the district judge noted that Upchurch and his coun-
sel had “no excuse” for failing to comply with discovery obli-
gations. The judge’s deadline for complying with his order
came and went with no response, so the O’Briens moved for
sanctions under Rule 37 in addition to their pending Rule 11
motion.
Less than a week after this second motion for sanctions,
Provis filed a notice of voluntary dismissal as to the O’Briens,
Lucareli, and the district attorney. Days later he filed a stipu-
lation signed by counsel for the three sheriff’s deputies agree-
ing to dismiss the case against them. Provis then filed a half-
page response to the O’Briens’ second sanctions motion, as-
serting that the court lacked jurisdiction to consider sanctions
because of the dismissal notices.
At this point Lucareli filed his own motion for sanctions
under Rule 11. In a minute order shortly thereafter, the judge
acknowledged receipt of the dismissal notice and stipulation
of dismissal and noted that these pleadings, taken together,
“terminate[d] the whole case.” But the judge retained

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6 No. 22-2541
jurisdiction over the three sanctions motions: the O’Briens’
motions under Rules 11 and 37, and Lucareli’s motion under
Rule 11.1
The judge eventually granted all three sanctions motions,
emphasizing that the case “should never have seen the light
of day.” Upchurch’s complaint “contained various, obvious
factual inaccuracies and was devoid of any reasonable basis
in existing law.” The judge also found that Upchurch had
filed the suit for an improper purpose—namely, to harass the
defendants. Finally, the judge held that sanctions under Rule
37 were warranted given the “unrebutted evidence” that Up-
church had failed to comply with the court’s discovery order.
For all these reasons, the judge concluded that an award of
costs and reasonable attorney’s fees was appropriate. He in-
vited the O’Briens and Lucareli to follow up with itemized re-
quests documenting their fees and costs. The judge also
ordered Provis to disgorge any fees that Upchurch had paid
him for his work on the lawsuit and deposit that sum with the
court.
The O’Briens and Lucareli promptly complied with the
judge’s order by submitting itemized requests for attorney’s
fees and costs. Provis responded by asking the judge not to
1 See Cooter & Gell v. Hartmax Corp., 496 U.S. 384, 396 (1990) (explaining
that the “imposition of a Rule 11 sanction,” “[l]ike the imposition of costs
[and] attorney’s fees, … is not a judgment on the merits,” so the “determi-
nation may be made after the principal suit has been terminated”); Dunn
v. Gull, 990 F.2d 348, 350 (7th Cir. 1993) (determining that a district court
“maintained jurisdiction over the sanctions motion”—which had sought
sanctions under Rule 11 and Rule 37—even though the court had previ-
ously granted a dismissal under Rule 41(a)(2) of the Federal Rules of Civil
Procedure).

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No. 22-2541 7
require disgorgement of the $10,000 retainer that Upchurch
had paid him. He disclosed that Upchurch had sued him in
small-claims court to recover payment, and that he and his
client were litigating over $4,000 of the retainer that remained
unspent. Provis explained that he was taking “responsibility
for his mistake” and was “not putting up any defense,” so
making him disgorge his retainer to the court would prevent
Upchurch from getting his money back.
Upchurch then filed his own response. Rather than contest
the itemized fee requests, he simply tried to relitigate whether
sanctions were warranted in the first place. Provis did the
same in another nonresponsive filing; in this document he ar-
gued for the first time that sanctions could not be imposed
without a hearing.
In an order entered on July 26, 2022, the judge resolved all
remaining matters. He awarded the costs and attorney’s fees
the O’Briens and Lucareli had requested. He declined to re-
scind his disgorgement order, but he modified it to a limited
extent: if Upchurch had already recovered some of his re-
tainer in small-claims court, the disgorgement amount could
be reduced commensurately. Finally, he rejected Provis’s re-
quest for a hearing as unnecessary. On August 4 the O’Briens
asked the judge to “enter judgment” based on the July 26 or-
der. The judge did so that same day, restating the same fee
awards from the July 26 order. Upchurch filed a notice of ap-
peal on August 31.
II. Discussion
Our threshold question is appellate jurisdiction. After Up-
church appealed, the O’Briens moved to dismiss the appeal as
untimely. We decided to take that motion—and an

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8 No. 22-2541
accompanying motion for frivolous-appeal sanctions under
Rule 38—with the merits of the case. We directed the parties
to address jurisdiction in their briefs; we also encouraged the
O’Briens and Lucareli to file a joint brief. They obliged.
Provis continues to represent Upchurch on appeal. (We
don’t know whether or how the dispute over his retainer was
resolved.) He did not meaningfully engage with the question
of appellate jurisdiction and did not respond at all to the ar-
gument about Rule 38 sanctions, either in his opening brief or
reply. Instead, he offered a largely incoherent and ultimately
frivolous argument about the judge’s failure to hold a hearing
before imposing sanctions. (More on that later.)
We begin, as we must, with the jurisdictional question. A
party who wishes to appeal a judgment or order in a civil case
must file a notice of appeal “within thirty days after the entry
of such judgment, order or decree.” The statutory time limit
“is a jurisdictional requirement.” Bowles v. Russell, 551 U.S.
205, 214 (2007). In limited circumstances the district court may
upon motion extend or reopen the time for appeal, see 28
U.S.C. § 2107(c), but Upchurch did not pursue this option. So
if his notice of appeal was filed outside the 30-day window
required by § 2107(a), we must dismiss the appeal for lack of
jurisdiction.
The timeliness question turns on whether the July 26 order
or the August 4 judgment is the operative “entry” for pur-
poses of the statutory deadline. If the judge’s July 26 order
triggered the countdown, then Upchurch’s appeal is untimely
because he did not file his notice of appeal within the 30-day
statutory deadline from that date. But if the August 4 judg-
ment provides the relevant date, then the appeal is timely.

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No. 22-2541 9
The Federal Rules of Appellate Procedure provide the
starting point for determining which date governs. Rule 4
starts the timer for filing a notice of appeal upon the “entry of
the judgment or order appealed from.” FED. R. APP.
P. 4(a)(1)(A); see also Perry v. Sheet Metal Workers’ Local No. 73
Pension Fund, 585 F.3d 358, 361 (7th Cir. 2009). Rule 4 also tells
us that Rule 58 of the Federal Rules of Civil Procedure, which
specifies the procedures for entering judgment and some-
times requires a separate document, affects how we decide
when the relevant entry occurs. When Rule 58 requires a sep-
arate document to enter judgment, Rule 4 starts the appeals
clock at the earlier of two occurrences: when the separate doc-
ument is entered or when 150 days have run since the order
or judgment was entered in the civil docket. See FED. R. APP.
P. 4(a)(7)(A)(ii). But when Rule 58 does not require a separate
document, the clock starts “when the judgment or order is en-
tered in the civil docket.” Id. 4(a)(7)(A)(i).2
2 We recognize that the Federal Rules of Appellate Procedure are not ju-
risdictional when they impose time prescriptions that are “absent from the
U.S. Code.” Hamer v. Neighborhood Hous. Servs. of Chi., 583 U.S. 17, 27
(2017). We also recognize that Rule 4 refers to the entry of a judgment or
order “for purposes of this Rule 4(a).” FED. R. APP. P. 4(a)(7)(A). But the
mere involvement of the Federal Rules of Appellate and Civil Procedure
does not eliminate the jurisdictional character of the timeliness question
presented here, which turns on compliance with § 2107(a)—a “time pre-
scription … imposed by Congress.” Hamer, 583 U.S. at 27. In other words,
a jurisdictional requirement is still jurisdictional even if federal rules—
which may not be jurisdictional themselves—inform our analysis of com-
pliance with that requirement. See Bankers Trust Co. v. Mallis, 435 U.S. 381,
384 (1978) (“The sole purpose of the separate-document requirement,
which was added to Rule 58 in 1963, was to clarify when the time for ap-
peal under 28 U.S.C. § 2107 begins to run.”); Wis. Cent. Ltd. v. TiEnergy,
LLC, 894 F.3d 851, 854 (7th Cir. 2018) (Barrett, J.) (“Rule 58’s ‘separate

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10 No. 22-2541
So where does this leave us? The timeliness of the appeal
depends on whether the judge’s July 26 order—which
granted the requests for attorney’s fees pursuant to the sanc-
tions order and set the award amounts—required a separate
judgment under Rule 58. If it did, then August 4 is the opera-
tive date because that’s when the judge “set forth” the July 26
order “on a separate document.” FED. R. APP. P. 4(a)(7)(A)(ii).
But if it did not require a separate judgment document, then
the July 26 order itself is the relevant entry for assessing com-
pliance with § 2107(a).3
Although Rule 58(a) generally requires that “[e]very judg-
ment … be set out in a separate document,” some orders are
exempt. Specifically, “a separate document is not required for
an order disposing of a motion for attorney’s fees under Rule
document’ requirement is important because it keeps jurisdictional lines
clear.” (emphasis added)). To enforce § 2107(a)’s jurisdictional require-
ment, we must decide which docket entry triggered the 30-day clock, and
doing so requires analysis of the federal rules. But the overarching timeli-
ness issue remains jurisdictional. See Nutrition Distrib. LLC v. IronMag Labs,
LLC, 978 F.3d 1068, 1072 (9th Cir. 2020) (explaining that the 30-day period
for appealing is jurisdictional because it is “based in statute” and that the
“Federal Rules of Appellate and Civil Procedure work in combination to
set forth the rules governing when notices of appeal must be filed”); Leavy
v. Hutchison, 952 F.3d 830, 831–32 (6th Cir. 2020) (per curiam) (dismissing
for lack of jurisdiction after consulting Rule 4 and Rule 58 to determine
“which document starts the clock”); United States v. Bradley, 882 F.3d 390,
394 (2d Cir. 2018) (same).
3 If Rule 58(a) did not require a separate document, the mere fact that the
judge entered a judgment on August 4 with no material differences would
not restart the time to appeal. See Leavy, 952 F.3d at 831 (“That the district
court later entered a formal judgment … does not change the appeal dead-
line or restart the clock.”); see also Groves v. United States, 941 F.3d 315, 324
(7th Cir. 2019) (Barrett, J.).

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No. 22-2541 11
54.” FED. R. CIV. P. 58(a)(3). The O’Briens and Lucareli argue
that the judge’s July 26 order falls squarely within this excep-
tion.
As we’ve noted, Upchurch completely failed to engage
with the relevant inquiry. He did not address the interaction
between Rule 4 and Rule 58, and his reply brief selectively
quotes § 2107 to suggest that only “judgments” can trigger the
30-day clock. But the statute, of course, refers to “any judg-
ment, order or decree.” § 2107(a) (emphasis added). Because
our jurisdiction is at issue, however, we consider a potential
wrinkle that Upchurch has not identified: Does it matter that
the judge awarded attorney’s fees under Rule 11 and Rule 37
rather than “under Rule 54” explicitly?
It does not. Under our precedent, the request for attorney’s
fees need not arise under Rule 54 expressly for the
Rule 58(a)(3) exception to apply. In Feldman v. Olin Corpora-
tion, 673 F.3d 515, 516–17 (7th Cir. 2012), sanctioned attorneys
contended that Rule 58(a)(3) was inapplicable because “the
award of fees against them was based in part on Rule 11” and
therefore was “outside the scope of Rule 54.” We rejected this
argument, reasoning that Rule 54 is “the rule on judgments”
and “makes awards of attorneys’ fees one type of judgment.”
Id. at 517 (emphasis added). And Rule 58(a)(3)’s reference to
Rule 54 merely “designates” that “type of judgment” as one
“for which a separate judgment document is not required.”
Id. We observed, importantly, that “Rule 54 does not create a
right to seek attorneys’ fees.” Id. Rather, the right to seek an
award of attorney’s fees is found elsewhere in the statutes and
rules. Id. We saw no reason why some orders disposing of fee
requests “should be subject to one [appeal] deadline” and
other orders “subject to another” depending on the basis—

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12 No. 22-2541
whether found in a statute or rule—for granting attorney’s
fees. Id. In sum, the Rule 11 sanction in Feldman “took the form
of an order to pay attorneys’ fees,” so it was “under Rule 54”
for purposes of Rule 58(a)(3). Id.
Although this is not a frequently litigated issue, our distil-
lation of the interaction between these rules in Feldman is not
an outlier. See Perez v. AC Roosevelt Food Corp., 744 F.3d 39, 40–
42 (2d Cir. 2013) (citing Feldman favorably and holding that “a
final order solely on the issue of attorneys’ fees is appealable
without entry of a separate document”); 2 STEVEN S. GENSLER
& LUMEN N. MULLIGAN, FEDERAL RULES OF CIVIL PROCEDURE,
RULES AND COMMENTARY, RULE 58, at 224 n.18 (Feb. 2023 up-
date) (citing Feldman and noting that while “the relationship
between Rule 58 and Rule 54 is confusing … , the end result
is simple: fee orders do not require a separate document of
judgment, so the time to appeal them starts to run as soon as
the order is entered on the docket”).
Applying Feldman, the judge’s July 26 order finally dispos-
ing of the motions for attorney’s fees did not require a sepa-
rate document, so it provides the relevant date for assessing
the timeliness of Upchurch’s appeal. This means that Up-
church’s notice of appeal—filed on August 31—was too late.
The appeal must be dismissed for lack of jurisdiction.
That leaves the motion for appellate sanctions under Rule
38. Because a Rule 38 sanctions request is not a merits deter-
mination, we may consider it even though we lack jurisdiction
over Upchurch’s appeal. See Cooke v. Jackson Nat’l Life Ins. Co.,
882 F.3d 630, 632–33 (7th Cir. 2018) (dismissing an appeal for
lack of jurisdiction but considering a request for Rule 38 sanc-
tions); cf. Willy v. Coastal Corp., 503 U.S. 131, 138 (1992) (ex-
plaining that a Rule 11 sanction “is not a judgment on the

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No. 22-2541 13
merits,” so it “does not raise the issue of a district court adju-
dicating the merits of a case or controversy over which it lacks
jurisdiction” (quotation marks omitted)). As we’ve noted, Up-
church did not respond to the motion for Rule 38 sanctions in
his opening brief. His reply brief is also silent on the subject,
even though the O’Briens and Lucareli devoted an entire sec-
tion of their joint response brief to the request for sanctions.
Given the lack of response, we can be brief. Rule 38 per-
mits us to sanction an appellant or his attorney when an ap-
peal is frivolous. See Salata v. Weyerhaeuser Co., 757 F.3d 695,
701 (7th Cir. 2014). “An appeal is frivolous when the result is
obvious or when the appellant’s argument is wholly without
merit.” Brotherhood of Locomotive Eng’rs & Trainmen v. Union
Pac. R.R. Co., 905 F.3d 537, 544 (7th Cir. 2018) (quotation marks
omitted). When that’s the case, Rule 38 sanctions serve “to
compensate the appellee for the time and resources wasted in
defending against a plainly baseless appeal.” Id. at 545.
This appeal is frivolous in more ways than one.
Upchurch’s opening brief and reply, spanning fewer than
eight combined pages, utterly failed to articulate a coherent
argument on the jurisdictional issue. He did not engage at all
with the central question of the exception to the separate-doc-
ument requirement under Rule 58(a)(3). And the lone refer-
ence to § 2107 is a misleading quotation suggesting that only
a “judgment” may start the appeals clock, even though the
statute plainly states that an “order” may do so too. § 2107(a)
(“[N]o appeal shall bring any judgment, order or decree in a[]
[civil case] … unless notice of appeal is filed, within thirty
days after the entry of such judgment, order or decree.” (em-
phases added)).

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14 No. 22-2541
Provis’s merits argument on his client’s behalf is largely
unintelligible. He insists that “Eighth Amendment (Excessive
Fines Clause) Due Process” required the judge to hold a hear-
ing before imposing sanctions. The Eighth Amendment, of
course, does not have a due-process clause, and the Excessive
Fines Clause has no bearing on this case, as Provis conceded
in his reply brief. His Fifth Amendment due-process argu-
ment amounts to a “bald conclusion,” Jaworski v. Master Hand
Contractors, Inc., 882 F.3d 686, 691 (7th Cir. 2018), that the
judge had a constitutional duty to hold a hearing before im-
posing sanctions. But Provis’s tardy request for a hearing,
which came after the judge had already addressed the sub-
stance of the sanctions motions, failed to explain what a hear-
ing would accomplish or why one was required. See In re
Rimsat, Ltd., 212 F.3d 1039, 1046 (7th Cir. 2000) (“Since a court
is not invariably required to provide a hearing before impos-
ing sanctions, the appellants’ failure to request a hearing
waives any right they might have had to one.”). Provis’s ar-
gument about the lack of a hearing is procedurally and sub-
stantively frivolous.
In short, after making the O’Briens and Lucareli spend
time and money dealing with a lawsuit that “should never
have seen the light of day,” Upchurch and Provis prolonged
this vexatious litigation by requiring them to defend a frivo-
lous appeal challenging the district judge’s sanctions order—
“the capstone of litigation that is hollow in every particular.”
Berwick Grain Co. v. Ill. Dep’t of Agric., 217 F.3d 502, 506
(7th Cir. 2000) (quoting Greening v. Moran, 953 F.2d 301, 307
(7th Cir. 1992)).
Rule 38 sanctions are amply justified. We will follow the
district judge’s lead in making Provis and Upchurch jointly

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No. 22-2541 15
and severally liable for the costs and reasonable attorney’s
fees required to defend this frivolous appeal. Even if Up-
church insisted that Provis keep this frivolous litigation going
through appellate review, Provis had a “legal duty not to yield
to such importuning[], and he open[ed] himself to sanctions”
when he failed to do his duty. Midlock v. Apple Vacations W.,
Inc., 406 F.3d 453, 458 (7th Cir. 2005).
Accordingly, the appeal is dismissed for lack of jurisdic-
tion. Provis and Upchurch are jointly and severally liable for
the costs and reasonable attorney’s fees incurred in defending
the appeal. Within 15 days, the O’Briens and Lucareli may
submit an accounting of their fees and costs. The clerk of court
shall send a copy of this opinion, and the district court’s sanc-
tions order, to the Wisconsin Office of Lawyer Regulation for
any action it deems appropriate.
DISMISSED FOR LACK OF JURISDICTION, WITH SANCTIONS

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