Sterling National Bank v. Bernard N. Block

In the
United States Court of Appeals
For the Seventh Circuit
____________________
Nos. 19‐2300, 19‐3122, & 19‐3235
S TERLING NATIONAL BANK ,
Plaintiff/Counterclaim Defendant‐
Appellant/Cross‐Appellee,
v.
BERNARD N. BLOCK , et al.,
Defendants/Counterclaim Plaintiffs‐
Appellees/Cross‐Appellants.
____________________
Appeals from the United States District Court for the
Northern District of Illinois, Eastern Division.
No. 1:16‐cv‐09009 — Harry D. Leinenweber, Judge.
____________________
A RGUED SEPTEMBER 23, 2020 — D ECIDED J ANUARY 5, 2021
____________________
Before SYKES , Chief Judge, and HAMILTON and ST . EVE , Cir‐
cuit Judges.
HAMILTON , Circuit Judge. In 2015, plaintiff Sterling Na‐
tional Bank purchased the Damian Services Corporation from
its prior owners (the defendant Sellers). The stock purchase
agreement set up an escrow of two million dollars available
to resolve disputes that might arise after the purchase. The

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2 Nos. 19‐2300, 19‐3122, & 19‐3235
parties dispute here the right to the escrowed money. The is‐
sues are governed by the elaborate Stock Purchase Agreement
in which the parties set up a comprehensive, custom‐tailored
set of rights, obligations, remedies, and procedures for resolv‐
ing disputes.
Shortly after the purchase, a disgruntled former Damian
employee called some of Damian’s clients to tell them of a bill‐
ing practice that the Sellers had instituted years earlier. When
Sterling learned of the situation, it investigated with the help
of a law firm and forensic accountant. After several months,
Sterling concluded that under the Sellers’ management,
Damian had overcharged its clients by over one million dol‐
lars. Sterling refunded these overpayments to each of its cur‐
rent clients, but not to any former clients.
Sterling then demanded indemnification from the escrow.
Sterling claimed that the Sellers had misrepresented
Damian’s liabilities and vulnerability to litigation. The Sellers
refused, leading to this lawsuit. The district court granted
summary judgment to the Sellers on the theory that Sterling
missed the seemingly strict deadline for claiming indemnifi‐
cation under the stock purchase agreement. The district court
then denied the Sellers’ request for statutory pre‐ and post‐
judgment interest on the escrow money. Both sides have ap‐
pealed.
We reverse summary judgment for the Sellers. Whether
Sterling’s demand for indemnification was late depends at
best on disputed facts. Even if the demand was late, however,
the agreement’s elaborate terms provide that any delay could
be held against Sterling only “to the extent that [Sellers] irrev‐
ocably forfeit[] rights or defenses by reason of such failure.”
Undisputed facts show that the Sellers have not irrevocably

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Nos. 19‐2300, 19‐3122, & 19‐3235 3
forfeited any claims or defenses, so the timing of Sterling’s de‐
mand does not matter. We decline both sides’ invitations to
decide the merits of Sterling’s claims as a matter of law in the
first instance. We agree with the district court’s denial of pre‐
and post‐judgment interest. We remand to the district court
for further proceedings on the merits.
I. Factual and Procedural Background
A. Damian’s Billing Practices
The Damian Services Corporation provides various ad‐
ministrative and payroll services to independent temporary
staffing companies (“temp agencies”). To explain the parties’
dispute, we must explain how Damian serves and bills its cli‐
ents. The baseline level of service, offered to “money‐only”
clients, is that Damian provides short‐term payroll funding to
pay the temp agencies’ employees. Damian offers other ser‐
vices to “full service” clients. Although Damian contracted
with its temp agency clients, it invoiced the end‐user compa‐
nies that hired the temporary workers. The end‐user employ‐
ers would then pay Damian, which would, in turn, send the
payments to the temp agencies after taking its cut as a fee for
its services.
Damian encourages its client staffing agencies to obtain
prompt payment from the end‐user employers. If the end‐
user employers pay quickly, then the temp agencies can pay
Damian faster and will be eligible for a discount. If an end‐
user waits too long and payment to Damian is delayed,
Damian assesses a late fee to its client. The parties agree that
Damian negotiated these discounts and fees (including tim‐
ing) with every client temp agency. Despite variations in rates

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4 Nos. 19‐2300, 19‐3122, & 19‐3235
and other terms, however, the underlying client contracts al‐
ways pegged these discounts and late fees to the invoice date.
The parties dispute the exact contours of Damian’s billing
and invoice‐dating practices before the 2009 change. In broad
brushstrokes, Damian would generally wait until it had re‐
ceived all the necessary information about each temporary
employee’s hours and rates before issuing an invoice. The in‐
voice would thus be issued and dated some time after the
workweek had ended—generally on a Friday, five business
days after the preceding Sunday. Damian marketed this delay
in processing payment as a benefit to potential clients.
In 2009, however, Damian began dating its invoices as of
the last day of the workweek, that is, Sunday. The date listed
on an invoice was thus earlier than not just the generation and
remission of the invoice, but also, in some cases, even
Damian’s receipt of the information needed to generate it.
This change gave Damian’s clients a narrower window to re‐
ceive early‐payment discounts and a larger chance of being
hit with late‐payment fees. Sterling refers to this practice as a
“backdating” scheme. For the sake of neutrality, we refer to it
more blandly as “the 2009 change.”
There is evidence that Damian took steps to hide the 2009
change from its clients. Damian never publicized the change,
although it had previously alerted its clients to other changes
in business practices that could affect them. There is also evi‐
dence that Damian developed a script for its employees to fol‐
low if a client ever complained. Employees were instructed to
tell the complaining client that they would “look into it,”
would seek approval for a “change back” to the previous bill‐
ing scheme, and, if a change were approved, would refund
fees and tell the client that Damian would have caught the

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Nos. 19‐2300, 19‐3122, & 19‐3235 5
(deliberate) dating change by the end of the quarter. Several
clients noticed and complained, but dozens of other did not.
B. Sale, Investigation, and Indemnification Demand
More than five years later, on February 27, 2015, the Sellers
sold Damian to Sterling for a little over $25 million. Under
what we call “the Agreement,” the Stock Purchase Agreement
at the center of these appeals, Sterling deposited two million
dollars of the purchase price in an escrow account. If no dis‐
putes arose by December 31, 2015, one million dollars would
be released to the Sellers, and the rest would be released in
August 2016, eighteen months after closing.
In July 2015, soon after the closing, a former Damian em‐
ployee began contacting Damian clients to expose the 2009
change. Sterling, which says it had not known before about
the 2009 change, quickly investigated. It retained the law firm
Wachtell, Lipton, Rosen & Katz to investigate. Sterling also
placed an internal hold on all documents relevant to the in‐
vestigation and told Damian’s temp agency clients that it had
uncovered a billing discrepancy. By August 11, 2015, Wachtell
Lipton had prepared a preliminary memorandum on poten‐
tially fraudulent billing practices. The next day, Wachtell Lip‐
ton discussed its initial findings in a telephone call with the
U.S. Attorney’s Office in the Northern District of Illinois as a
potential case of corporate fraud. Sterling also hired a forensic
accounting firm, AlixPartners, which calculated that if the
2009 change had not occurred, Damian’s clients would have
saved $1,289,916 in discounts and avoided late fees.
As Wachtell Lipton wrapped up its investigation, it
drafted another memorandum, dated November 27, and pre‐
sented it to the U.S. Attorney’s Office on December 2. The

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6 Nos. 19‐2300, 19‐3122, & 19‐3235
prosecutors declined to take up the case. Nine days later, on
December 11, 2015, Sterling sent the Sellers a formal notice
demanding indemnification under the Agreement. Before the
Sellers responded, Sterling contacted each of Damian’s then‐
current clients that it had determined had been overcharged
and offered full refunds on the overcharges.
The Sellers rejected Sterling’s demand. They said that the
thirty‐page demand did not provide sufficient detail on how
the total amount was computed. The Sellers refused to partic‐
ipate in the Agreement’s process for resolving indemnifica‐
tion claims. As a result of the dispute, no escrow funds have
been released.
C. Procedural History
Sterling filed this suit in September 2016 seeking indemni‐
fication under the Agreement. Sterling’s claims arise under
state law; federal jurisdiction rests on diversity of citizenship.
The operative complaint alleges that the Sellers’ failure to dis‐
close the 2009 change and its consequences breached the
Sellers’ representations and warranties in the Agreement, and
that the Sellers breached the Agreement by refusing to indem‐
nify Sterling. The Sellers counterclaimed for, among other
things, a declaratory judgment holding that Sterling is not en‐
titled to indemnification and that the Sellers are entitled to
pre‐ and post‐judgment interest at 12% on the money in es‐
crow.
Sterling and the Sellers filed cross‐motions for summary
judgment. Sterling argued that undisputed facts showed that
the Sellers are liable for breaching warranties and representa‐
tions in the Agreement. The Sellers argued that Sterling failed

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Nos. 19‐2300, 19‐3122, & 19‐3235 7
to follow the Agreement’s procedures for demanding indem‐
nification. In the alternative, the Sellers argued that the 2009
change of invoice dates did not actually breach any underly‐
ing client contracts, so that no representations or warranties
were breached.
The district court granted summary judgment for the
Sellers on the narrow procedural ground that Sterling’s in‐
demnification notice was too late and that the delay preju‐
diced the Sellers. Sterling appealed. After some confusion
about whether any counterclaims remained pending, the dis‐
trict court reopened the case and then denied the Sellers’ mo‐
tion for pre‐ and post‐judgment interest. Although the district
court did not issue an amended Rule 58 judgment, both sides
appealed.
II. Appellate Jurisdiction
We must first consider whether these appeals are properly
before us. The lack of a separate, final Rule 58 judgment
makes the appellate jurisdiction picture messier than neces‐
sary. The district court noted in its summary judgment opin‐
ion that neither side had addressed all of the Sellers’ counter‐
claims but still entered judgment for the Sellers pursuant to
Rule 58. The court later reopened the case because some
claims had not yet been resolved. The Sellers then voluntarily
dismissed two of their counterclaims and explained that the
only remaining issues were whether they were entitled to pre‐
and post‐judgment interest and their costs. The court ruled on
those outstanding motions without issuing an amended Rule
58 judgment.
Rule 58 requires: “Every judgment and amended judg‐
ment must be set out in a separate document . . . .” Fed. R. Civ.

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8 Nos. 19‐2300, 19‐3122, & 19‐3235
P. 58(a). This “‘separate document’ requirement is important
because it keeps jurisdictional lines clear.” Wisconsin Central
Ltd. v. TiEnergy, LLC, 894 F.3d 851, 854 (7th Cir. 2018). This
formality is not, however, a “prerequisite to appealing. The
losing party can appeal a judgment … before the entry of the
Rule 58 judgment order if … the judgment really is final
within the meaning of 28 U.S.C. § 1291.” Borrero v. City of Chi‐
cago, 456 F.3d 698, 699–700 (7th Cir. 2006). We may exercise
appellate jurisdiction without an amended Rule 58 judgment
“if the district court has otherwise indicated its intent to fi‐
nally dispose of all claims.” Wisconsin Central, 894 F.3d at 854.
When a district court grants declaratory relief, the court
“must declare specifically and separately the respective rights
of the parties, not simply state in a memorandum opinion, mi‐
nute order, or a form prescribed for judgment in a civil case
that a motion has been granted or denied.” Calumet River
Fleeting, Inc. v. Int’l Union of Operating Engineers, Local 150,
AFL‐CIO, 824 F.3d 645, 651 (7th Cir. 2016) (cleaned up),
quoted in INTL FCStone Financial Inc. v. Jacobson, 950 F.3d 491,
502 (7th Cir. 2020). But “we may nevertheless have jurisdic‐
tion if the practicalities weigh heavily toward a common sense
conclusion that the district court intended to enter a final
judgment.” Id.1
Here, the district court’s opinions and orders show it in‐
tended to dispose of all claims. See Sterling National Bank v.
1 In a civil case where the district court has failed to render a Rule 58
judgment, “we treat judgment as entered 150 days after the entry of the
judgment or order on the civil docket.” Calumet River Fleeting, 824 F.3d at
650, citing Fed. R. Civ. P. 58(c)(2)(B) and Fed. R. App. P. 4(a)(7)(A)(ii).
Judgment here was effectively entered no later than March 8, 2020, 150
days after the district court resolved the last pending issues.

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Nos. 19‐2300, 19‐3122, & 19‐3235 9
Block, 2019 WL 5085715 (N.D. Ill. Oct. 10, 2019) (“Sterling II”)
(ruling on costs and pre‐ and post‐judgment interest); Sterling
National Bank v. Block, Case No. 16‐cv‐9009, Dkt. 182 (“The
case will not terminate until the Court issues a ruling on costs
and pre‐ and post‐judgment interest.”); see also Dkt. 206
(transcript of hearing memorialized by Dkt. 182). We expect a
more thorough accounting of each party’s respective rights
and obligations at the conclusion of an action seeking declar‐
atory relief. Still, we are confident that the district court in‐
tended to enter a final judgment here, especially since it de‐
nied the Sellers’ declaratory claim in full. See Calumet River
Fleeting, 824 F.3d at 651. Finally, the Sellers’ acknowledgment
at oral argument that they had withdrawn their remaining
counterclaims with prejudice assures us that the district court
disposed of all the claims before it. See Wetzel v. Glen St. An‐
drew Living Community, LLC, 901 F.3d 856, 867 (7th Cir. 2018)
(accepting similar concession). We therefore have jurisdiction
over these appeals.
III. Summary Judgment Standard
“We review a district court’s summary judgment ruling de
novo and consider the facts and draw all inferences in the
light most favorable to the nonmoving party.” Henry v. Hulett,
969 F.3d 769, 776 (7th Cir. 2020) (en banc); see also Black Earth
Meat Market, LLC v. Village of Black Earth, 834 F.3d 841, 847 (7th
Cir. 2016) (considering cross‐motions for summary judgment
“one at a time, construing all facts and drawing all reasonable
inferences in favor of the non‐moving party”). “Summary
judgment is appropriate when ‘there is no genuine dispute as
to any material fact and the movant is entitled to judgment as
a matter of law.’” Henry, 969 F.3d at 776, quoting Fed. R. Civ.

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10 Nos. 19‐2300, 19‐3122, & 19‐3235
P. 56(a). The parties agree that Illinois law applies to their
claims.
“The primary objective in construing a contract is to give
effect to the intent of the parties,” which is best shown by the
language of the contract itself. Gallagher v. Lenart, 226 Ill. 2d
208, 232–33, 314 Ill. Dec. 133, 148, 874 N.E.2d 43, 58 (2007). “If
the words in the contract are clear and unambiguous, they
must be given their plain, ordinary and popular meaning.”
Thompson v. Gordon, 241 Ill. 2d 428, 441, 349 Ill. Dec. 936, 944,
948 N.E.2d 39, 47 (2011), quoted in Soarus LLC v. Bolson Mate‐
rials Int’l Co., 905 F.3d 1009, 1011 (7th Cir. 2018). With contracts
with substantial stakes, negotiated between commercially so‐
phisticated parties, we interpret contracts “literally” because
such parties “know how to say what they mean and have an
incentive to draft their agreement carefully.” Bank of America,
N.A. v. Moglia, 330 F.3d 942, 946 (7th Cir. 2003) (applying Illi‐
nois law); see also West Bend Mut. Ins. Co. v. Procaccio Painting
& Drywall Co., 794 F.3d 666, 680 (7th Cir. 2015) (applying Illi‐
nois law and refusing to ignore contract’s plain meaning: the
“sophisticated contract partner[] [] easily could have included
the terms” it wanted to read into the contract); Central Illinois
Light Co. v. Home Ins. Co., 213 Ill. 2d 141, 156, 290 Ill. Dec. 155,
164, 821 N.E.2d 206, 215 (2004) (“[S]ophisticated business en‐
tities [] can be assumed to have specialized knowledge of the
contractual terms they employ.”).
All portions of a contract should be “construed as a whole,
viewing each part in light of the others.” Gallagher, 226 Ill. 2d
at 233, 314 Ill. Dec. at 148, 874 N.E.2d at 58. We also try to give
meaning to every provision of the contract and avoid render‐
ing any provisions superfluous. Land of Lincoln Goodwill In‐
dus., Inc. v. PNC Financial Servs. Grp., 762 F.3d 673, 679 (7th

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Nos. 19‐2300, 19‐3122, & 19‐3235 11
Cir. 2014) (applying Illinois law). At the same time, we should
also recognize that drafters of contracts, like drafters of stat‐
utes, may “intentionally err on the side of redundancy to ‘cap‐
ture the universe.’” See Abbe R. Gluck & Lisa Schultz Bress‐
man, Statutory Interpretation from the Inside—an Empirical
Study of Congressional Drafting, Delegation, and the Canons: Part
I, 65 Stan. L. Rev. 901, 934 (2013); see also Continental Casualty
Co. v. MidStates Reinsurance Corp., 388 Ill. Dec. 214, 219, 24
N.E.3d 122, 127 (Ill. App. 2014) (accepting that drafters of con‐
tract took the proverbial “belt and suspenders” approach ra‐
ther than straining to find different meanings).
IV. Compliance with Indemnification Procedures
The district court granted summary judgment to the
Sellers on the ground that the Agreement does not require in‐
demnification if the notice is too late and the delay causes ir‐
revocable harm. The court reasoned that Sterling’s notice was
late and left the Sellers without any way to challenge Ster‐
ling’s offers to reimburse Damian’s clients or its six‐figure in‐
vestigation budget.
On appeal, Sterling argues that the court made three er‐
rors. First, Sterling defends its notice as timely. Second, Ster‐
ling argues that even if its notice was late, any delay should
have no consequence because the Sellers have not irrevocably
forfeited any rights or defenses. Under the parties’ elaborate
Agreement, we conclude that the Sellers have not shown that
Sterling’s demand was late. Also, undisputed facts show that
even if Sterling’s demand had been late, the Sellers have not
irrevocably forfeited any rights or defenses by reason of any
delay. We need not reach Sterling’s third argument, that fac‐
tual disputes about the extent of any prejudice to the Sellers
preclude summary judgment.

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12 Nos. 19‐2300, 19‐3122, & 19‐3235
Section 8.05(c) of the Agreement provides the following
procedures for indemnification claims between the parties:
Direct Claims. Any Action by an Indemnified
Party on account of a Loss which does not result
from a Third Party Claim (a “Direct Claim”)
shall be asserted by the Indemnified Party giv‐
ing the Indemnifying Party reasonably prompt
written notice thereof, but in any event not later
than ten (10) days after the Indemnified Party
becomes aware of such Direct Claim. The failure
to give such prompt written notice shall not,
however, relieve the Indemnifying Part of its in‐
demnification obligations, except and only to
the extent that the Indemnifying Party irrevoca‐
bly forfeits rights or defenses by reason of such
failure. Such notice by the Indemnified Party
shall describe the Direct Claim in reasonable de‐
tail, shall include copies of all material written
evidence thereof and shall indicate the esti‐
mated amount, if reasonably practicable, of the
Loss that has been or may be sustained by the
Indemnified Party.
Late Notice?
We are not persuaded that Sterling’s demand was actually
late, or at least that the undisputed facts show it was late. The
Agreement required notice within ten days, but only after a
party became “aware of” the claim, and it required a demand
with “reasonable detail.” This combination makes for an am‐
biguous mess, at least as applied to this dispute. The parties
disagree about just how much Sterling needed to know before
being “aware of” its claim against the Sellers and whether a

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Nos. 19‐2300, 19‐3122, & 19‐3235 13
precise trigger is needed to start the ten‐day clock for notice.
According to Sterling, it did not become “aware of” its claim
until Wachtell Lipton completed its investigation, especially
since the Sellers contended that even the thirty‐page demand
that Sterling presented was not detailed enough to count as a
proper demand under the Agreement. The Sellers, on the
other hand, counter that Sterling became “aware of” the claim
no later than August 2015, when Sterling and Wachtell Lipton
first presented the basic facts surrounding the 2009 change to
the U.S. Attorney’s Office.
Section 8.05(c) of the Agreement built in inherent tension
between the need to investigate a Direct Claim before making
a demand and the need to make a demand within just ten
days after becoming “aware of” it. We have studied the
Agreement’s definitions of Direct Claims and Actions and the
need to support a demand for indemnification with a “reason‐
able” but uncertain quantum of evidence. We conclude that
whether Sterling’s demand came more than ten days after it
became “aware of” its Direct Claim cannot be decided in favor
of the Sellers as a matter of law. We also conclude that we need
not decide whether Sterling is entitled to summary judgment
on the issue. As we explain next, Sterling is entitled to sum‐
mary judgment on the notice issue on a different basis. Even
if its demand was late, the undisputed facts show that the
Sellers did not irrevocably forfeit any rights or defenses by
reason of the timing of Sterling’s demand.
B. Irrevocable Forfeiture?
Section 8.05(c) of the Agreement requires prompt notice of
a Direct Claim. Delay is excused, however, unless the Sellers
“irrevocably forfeit[] rights or defenses by reason of such fail‐
ure.” The Sellers claim that Sterling’s supposed delay caused

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14 Nos. 19‐2300, 19‐3122, & 19‐3235
them to forfeit three rights: (1) the right to settle the underly‐
ing claims with overcharged clients; (2) the right to litigate the
underlying breach‐of‐contract claims with overcharged cli‐
ents, including raising certain defenses; and (3) the right to
investigate as granted by the Agreement. The Sellers cannot
show, however, that they have irrevocably forfeited any of
these rights. Under § 8.05(c), therefore, the timing of Sterling’s
indemnification demand could not relieve the Sellers of a
duty to indemnify. See Dkt. 135, at *14–15 (Sterling’s request
for summary judgment on this issue); Dkt. 136, ¶ 66.
First, the Sellers have not irrevocably forfeited the right to
settle the underlying claims because they never had that right
to begin with. The Sellers argue that Sterling’s premature set‐
tlements of these claims with current clients for one hundred
cents on the dollar deprived them of their right to drive
harder bargains. The Sellers cite cases applying Illinois law in
the insurance context that have required notice to head off in‐
sureds’ incentives to overpay when playing with someone
else’s money.
The problem for the Sellers is that this case does not di‐
rectly involve any of Damian’s clients or temporary employ‐
ment payroll contracts. To use the Agreement’s terms, Ster‐
ling has asserted a Direct Claim, not a Third Party Claim: Ster‐
ling has sued the Sellers for concealing these potential liabili‐
ties. Whether Sterling actually paid refunds to Damian’s cli‐
ents or not does not tell us whether it was required to do so.
The key liability issue for indemnification is whether the
Sellers misrepresented anything in the Agreement. To be sure,
if a temp agency had ever sued or threatened to sue Damian
for the 2009 change after the 2015 purchase, that would have
been a Third Party Claim. Such a claim would have required

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Nos. 19‐2300, 19‐3122, & 19‐3235 15
the parties to consult before any settlement. See § 8.05(b)
(“Settlement of Third Party Claims”). But that is not what hap‐
pened. The cooperation clauses in § 8.05(b) simply do not ap‐
ply.
Moreover, the fact that the Agreement expressly requires
the parties to cooperate on Third Party Claims implies that
there is no such duty on Direct Claims, for which the Agree‐
ment says nothing about cooperation. See Land of Lincoln
Goodwill, 762 F.3d at 679 (“[W]e attempt to … avoid a con‐
struction that would render a provision superfluous.”); Rick‐
her v. Home Depot, Inc., 535 F.3d 661, 668 (7th Cir. 2008), dis‐
cussing Drexel State Bank of Chicago v. O’Donnell, 344 Ill. 173,
183, 176 N.E. 348, 352 (1931) (Illinois courts use expressio unius
canon as a rule of construction, but do not allow it to override
a contract’s unambiguous terms).
The Sellers’ citations to insurance cases miss the mark.
Many of those cases applied contract language expressly re‐
quiring cooperation during litigation or settlement. The par‐
ties here drafted their elaborate Agreement without requiring
cooperation for Direct Claims. Compare § 8.05(c), with Waste
Management, Inc. v. Int’l Surplus Lines Ins. Co., 144 Ill. 2d 178,
192, 161 Ill. Dec. 774, 779, 579 N.E.2d 322, 327 (1991) (“The co‐
operation clause in this case imposes upon insureds the duty
to assist insurers in the conduct of suits and in enforcing any
right to contribution or indemnity against persons potentially
liable to insureds.”); Country Mut. Ins. Co. v. Livorsi Marine,
Inc., 358 Ill. App. 3d 880, 882, 885, 295 Ill. Dec. 665, 666, 668,
833 N.E.2d 871, 872, 874 (2004) (distinguishing “notice of oc‐
currence” and “notice of lawsuit” cases because the contract
in question gave the insurer “the right and duty to defend any
suit” or to “settle any claim or suit”) (internal quotation marks

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16 Nos. 19‐2300, 19‐3122, & 19‐3235
omitted); American Country Ins. Co. v. Bruhn, 289 Ill. App. 3d
241, 244, 224 Ill. Dec. 805, 807, 682 N.E.2d 366, 368 (1997) (no‐
tice provision required insured to “[c]ooperate with [insurer]
in the investigation, settlement or defense of any claim or
suit”).
To be sure, some cases applying Illinois law have gone be‐
yond contractual texts to find implied remedies for lack of no‐
tice in contracts to give full effect to notice provisions. See,
e.g., Kerr v. Illinois Central R.R. Co., 283 Ill. App. 3d 574, 581–
82, 219 Ill. Dec. 81, 87, 670 N.E.2d 759, 765 (1996) (construing
notice provision to include implied remedy where excess in‐
surer did not reserve right to participate in defense of claim,
lest insurer “be called on simply to write the check”); see also
AU Electronics, Inc. v. Harleysville Grp., Inc., 82 F. Supp. 3d 805,
814 (N.D. Ill. 2015) (explaining rationale of Illinois insurance
rules as applied to contracts that “entitle the insurers to con‐
trol the insured’s defense against a covered claim and negoti‐
ate a settlement”).
The principal‐agent problems motivating the unusual,
non‐textual finding of an implied duty to cooperate in Kerr
are less relevant here because the underlying alleged contract
breaches were not with strangers but with Damian’s clients.
And apart from policy arguments, the Sellers’ contention that
the notice requirement implicitly granted the Sellers a right to
bargain independently with their former clients is not
supported by the text of the sophisticated parties’ elaborate
Agreement. Nothing in the language of the Agreement
required Sterling to involve the Sellers in any settlement
negotiations or to allow the Sellers to settle the claims
themselves. It would seem odd to give the Sellers the ability
to poison the relationship between Damian and its clients.

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Nos. 19‐2300, 19‐3122, & 19‐3235 17
Odd enough, anyway, not to find an implied right to do so.
Any exception that might be gleaned from Kerr does not
apply here, so any supposed delay in giving notice of the
indemnification claim did not cause the Sellers to lose a right
secured by the Agreement.
Second, the Sellers also have not irrevocably forfeited the
right to litigate the underlying contract claims. They are in
fact litigating the merits of those claims in this case. They can
still assert contract defenses, and the merits of Sterling’s claim
hinge on whether the underlying hypothetical contract claims
against Damian would have had any merit. That is, even
though the temp agency clients are not parties to this litiga‐
tion, Sterling must still show that Damian was liable to them.
The Sellers can litigate these claims now.
The Sellers counter that this reading unduly narrows their
rights to litigate the claims. Their theory seems to be that they
will have a more difficult time proving damages now that
some but not all clients have already been reimbursed. But the
parties here are commercially sophisticated. They wrote their
Agreement to nullify an indemnification demand for delay
only if and to the extent the delay resulted in “irrevocable for‐
feiture” of a claim or defense. That’s a high bar. If they had
wanted the Agreement to bar indemnification if late notice
merely impeded or weakened a claim or defense, they could
have said so. E.g., Procaccio Painting, 794 F.3d at 680.
Third, the Sellers have not irrevocably forfeited any inves‐
tigation rights. The relevant provisions of § 8.05(c) are in some
tension on this point:

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18 Nos. 19‐2300, 19‐3122, & 19‐3235
The Indemnified Party shall allow the Indemni‐
fying Party and its professional advisors to in‐
vestigate the matter or circumstance alleged to
give rise to the Direct Claim, and whether and
to what extent any amount is payable in respect
of the Direct Claim and the Indemnified Party
shall assist the Indemnifying Party’s investiga‐
tion by giving such information and assistance
(including access to the Company’s premises
and personnel and the right to examine and
copy any accounts, documents or records) as the
Indemnifying Party or any of its professional
advisors may reasonably request.
The Sellers claim that this language gave them a right to par‐
ticipate in Sterling’s internal, pre‐claim investigation, which
they say was irrevocably lost when Sterling investigated on
its own. The Sellers also contend that they have lost the right
to conduct their own timely investigation because (a) infor‐
mation about the settlement value of the underlying claims is
now unobtainable, (b) any subsequent investigation would be
rendered a nullity because Sterling paid the clients already,
and (c) Sterling unfairly blocked third‐party discovery in this
case.
The Sellers’ arguments assert rights not granted by the
Agreement. Section 8.05(c) of the Agreement is ambiguous in
important respects, but it quite plainly assumes that Sterling
would need to conduct some investigation of its own before
giving notice of a Direct Claim for indemnification. The
Agreement required Sterling, in giving formal notice, to “de‐
scribe the Direct Claim in reasonable detail, [] include copies

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Nos. 19‐2300, 19‐3122, & 19‐3235 19
of all material written evidence thereof and [] indicate the es‐
timated amount … of the Loss.” § 8.05(c). Sterling could not
have met that requirement without a substantial pre‐demand
investigation.
The Sellers’ asserted right to investigate must be consistent
with these requirements. Nothing in the Agreement granted
the Sellers a right to conduct a contemporaneous investiga‐
tion even before Sterling gave notice of its demand. Perhaps,
as the Sellers suggest, it was unreasonable for Sterling to run
up $650,000 in investigation costs. If so, that issue would affect
only whether the professional fees were indemnifiable
“Losses,” not whether one can find an implied (and illogical)
right for an indemnifying party to conduct its own investiga‐
tion even before a demand is made.
The Agreement refers to the “Indemnifying Party’s inves‐
tigation,” not to the “Indemnifying Party’s participation in the
Indemnified Party’s investigation,” which would make little
sense. After demand is made, according to the Agreement, the
Sellers had a limited right of access to documents and person‐
nel. The Sellers had that right whether the notice was late or
timely, but they did not have a right to do more earlier.
The Sellers also complain about being denied the right to
depose certain clients of Damian under the Federal Rules of
Civil Procedure in this action. The Sellers’ argument on this
point is difficult to follow. Nothing in the Agreement itself
provides—or could provide—the right to subpoena third par‐
ties through the parties’ private dispute‐resolution proce‐
dures. The Federal Rules of Civil Procedure apply in this case,
of course, but on appeal, the Sellers have not challenged any
case‐management limits on depositions. On remand, the dis‐

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20 Nos. 19‐2300, 19‐3122, & 19‐3235
trict court may of course choose to revisit the scope of discov‐
ery, but nothing about this dispute relieves the Sellers of any
otherwise valid claim for indemnification.
The Sellers’ original response to the indemnification de‐
mand underscores that any right to investigate is far more
limited than they argue now. As noted, the Sellers objected to
Sterling’s thirty‐page demand for indemnification on the
ground that it did not provide enough detail. That is, the
Sellers claimed the demand was insufficient under the Agree‐
ment unless and until Sterling provided the kinds of docu‐
mentation that could have come only from an investigation
that would have been even more thorough than the one that
the Sellers now argue took too long and was too expensive.
Along those lines, the Sellers also argue that the right to
investigate was lost because Sterling prematurely settled any
outstanding claims by customers. We reject this attempt to re‐
cast the first two arguments within the framework of the in‐
vestigation for the reasons above. The Agreement simply did
not grant the Sellers a right to negotiate with third parties in
addressing a Direct Claim like this. And even if the Sellers lost
the ability to learn exactly what each current client might have
accepted as a settlement offer for purposes of computing
damages in this lawsuit, they have not lost access to Damian’s
former clients, who have not yet been paid. The Sellers have
not irrevocably lost any opportunity to investigate the
amounts for which temp agencies would settle.2
2 We need not resolve Sterling’s back‐up argument that disputed facts
about the extent to which the Sellers were harmed require remand for trial.
Section 8.05(c) relieves the Sellers of a duty to indemnify only “to the ex‐
tent that the Indemnifying Party irrevocably forfeits rights or defenses.”
Our conclusion that the extent of irrevocable harm was zero resolves this

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Nos. 19‐2300, 19‐3122, & 19‐3235 21
V. Directing Summary Judgment on Other Grounds?
Looking beyond the notice issues, both sides also contend
that they should prevail as a matter of law on issues the dis‐
trict court did not address. Their arguments focus on the mer‐
its of the underlying contract disputes that Damian’s clients
might have raised based on the 2009 change in dating in‐
voices.
We are not convinced that either side should prevail as a
matter of law on the merits of those hypothetical claims for
breach of contract. To highlight just two of our concerns, the
underlying client contracts did not include specific language
on how invoices should be dated. That silence may make it
impossible to decide with one stroke whether the 2009 change
did or did not breach all of those contracts. The evidence of
the Sellers’ misleading script for calming any restless clients
supports an inference that the Sellers knew the 2009 change
was not authorized and could lead to unhappy clients and
even litigation. On the other hand, the fact that no clients ever
sued and that most apparently never noticed the 2009 change
supports an inference that it was not a significant concern to
them.3
issue. In any event, the district court’s grant of judgment as a matter of
law would have been erroneous even if the Sellers had demonstrated some
irrevocable harm because they did not show that, taking all the evidence
in the light most favorable to Sterling, the Sellers had forfeited their entire
case, that is, that the extent of forfeiture was complete.
3 The Sellers’ brief argues that the client contracts required Damian to
“render” the invoices promptly at the end of the workweek and that these
provisions implicitly also required dating the invoices as of the end of the
workweek. But at oral argument, the Sellers conceded that they did not

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22 Nos. 19‐2300, 19‐3122, & 19‐3235
To the extent that either side relies on a course of dealing
or other evidence beyond the inconclusive text of the client
contracts themselves, it may be impossible to decide the mer‐
its of those hypothetical claims without a close look at
Damian’s dealings with each client. That course would be a
poor candidate for summary judgment, let alone an appellate
decision in the first instance. See International Financial Servs.
Corp. v. Chromas Technologies Canada, Inc., 356 F.3d 731, 740
(7th Cir. 2004) (refusing to direct summary judgment on issue
that “depends on a host of considerations that this court is ill‐
positioned to weigh as a matter of first impression”).
VI. Pre‐judgment Interest Under the Agreement
The district court held that the Sellers were entitled to the
two million dollars in escrow but were not entitled to pre‐
judgment interest on the funds. Sterling II, 2019 WL 5085715,
at *6. We must set aside the ruling that the Sellers are entitled
to the escrow funds, but the issue of pre‐judgment interest is
likely to arise on remand. Those funds will eventually need to
be distributed to someone. We agree with the district court
that, under the terms of the parties’ Agreement, pre‐judgment
interest is not available.
As a general matter, in a contract dispute like this one, pre‐
judgment interest may be awarded under state law as a matter
of statute or contract. See Procaccio Painting, 794 F.3d at 680
(turning to state law); Kouzoukas v. Retirement Board of Police‐
men’s Annuity & Benefit Fund of City of Chicago, 234 Ill. 2d 446,
“render” the invoices until after the invoice date. Because the client con‐
tracts did not speak to dating and the only arguably relevant contract lan‐
guage is inapposite, we cannot decide this case based on only the “render”
language.

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Nos. 19‐2300, 19‐3122, & 19‐3235 23
474, 334 Ill. Dec. 924, 940, 917 N.E.2d 999, 1015 (2009) (“As a
general rule, prejudgment interest is recoverable only where
authorized by the agreement of the parties or by statute.”).
The Sellers argue they were entitled to pre‐judgment in‐
terest under the Illinois Interest Act, 815 ILCS 205/2, which
authorizes interest awards for “all moneys after they become
due on any bond, bill, promissory note, or other instrument
of writing” and “money withheld by an unreasonable and
vexatious delay of payment.” Sterling counters that the
Agreement expressly waived prejudgment interest outside of
the indemnification framework and that the Sellers failed to
comply with the indemnification procedures in seeking inter‐
est.
Several Agreement provisions are relevant. First, Section I
identifies “interest” as a form of “Losses.” The Agreement
also has an expansive “Exclusive Remedies” provision in
which “the parties acknowledge and agree that their sole and
exclusive remedy with respect to any and all claims (other than
claims arising from … intentional misconduct …) for any
breach of any representation, warranty, covenant, agreement
or obligation set forth herein or otherwise relating to the sub‐
ject matter of this Agreement shall be pursuant to the indem‐
nification provisions . . . .” § 8.09 (emphasis added). Likewise,
“each party [] waives, to the fullest extent permitted under
Law, any and all rights, claims and causes of action for any
breach of any representation, warranty, covenant, agreement
or obligation set forth herein or otherwise relating to the sub‐
ject matter of this Agreement it may have against the other
parties hereto … except pursuant to the indemnification pro‐
visions.” Id.

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24 Nos. 19‐2300, 19‐3122, & 19‐3235
Section 8.03 explains when the Sellers may seek indemni‐
fication: for “any and all Losses incurred or sustained by, or
imposed upon the Seller Indemnitees based upon, arising out
of, with respect to or by reason of[] … any breach or non‐ful‐
fillment of any covenant, agreement or obligation to be per‐
formed by Buyer pursuant to this Agreement.”
The Agreement required that two million dollars be de‐
posited into the escrow account at closing, with one million to
be released to the Sellers on December 31, 2015, and the rest
to be released eighteen months after closing, in August 2016.
§ 2.02(b). These funds, however, were not to be released “in
the event one or more claims have been asserted by Buyer
against Seller” pursuant to the indemnity provisions. Id. In
that case, Sterling was to “reasonably estimate the amount of
Losses that could reasonably be incurred by [Sterling] if such
Asserted Claims were successful (the ‘Reserve’).” Id. In the
event Sterling makes a claim, the Reserve may not be released.
The parties also signed a separate Escrow Agreement, which
included provisions allowing the parties to agree to move the
escrow funds to alternate interest‐bearing investment ac‐
counts. See generally Dkt. 20‐2. The Agreement also included
a custom‐tailored provision for post‐judgment interest, calling
for interest to accrue at 12%, but not starting until five busi‐
ness days after an agreement to pay or a “final, non‐appeala‐
ble adjudication.” § 8.06(a).
The Sellers have not shown that they complied with the
indemnification procedures described above to demand inter‐
est. They became aware of Sterling’s Direct Claim on Decem‐
ber 11, 2015 and responded by the end of that month, yet it is
not clear that they ever provided proper notice of a claim for

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Nos. 19‐2300, 19‐3122, & 19‐3235 25
interest. The parties had plenty of opportunities to put the es‐
crowed funds in an interest‐bearing account, yet they never
did so.
Apart from the Sellers’ ironic failure to follow the same in‐
demnification notice procedures that they insist Sterling
failed to follow, neither the Agreement nor the Illinois Interest
Act provides for pre‐judgment interest here. The Agreement
acknowledges that interest may be available as a Loss, but it
funnels all claims through the indemnification provisions.
Those terms allow the Sellers to recoup Losses only for
breaches of the Agreement. Here, the Agreement did not re‐
quire the release of funds that “could be reasonably incurred
by [Sterling] if such Asserted Claims were successful.” Im‐
portantly, “reasonably” modifies the dollar value of the
claims if successful, not the probability of victory on any
claims.
Sterling’s demand for the entire two million dollars may
or may not succeed in the end, but it was not unreasonable as
a matter of law for Sterling to make the demand. A forensic
accounting firm estimated that Damian overcharged its cli‐
ents by almost $1.3 million, and Wachtell Lipton and the fo‐
rensic accountant billed hundreds of thousands of dollars.
The costs of enforcing the indemnification provision were also
uncertain. If Sterling did not breach the Agreement by de‐
manding indemnification, the Agreement bars pre‐judgment
interest.
To avoid this logic, the Sellers cite Katzman v. Helen of Troy
Texas Corp., 2013 WL 1496952 (S.D.N.Y. Apr. 11, 2013), in
which a district court held that a similarly broad waiver of
non‐indemnification remedies did not foreclose statutory in‐

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26 Nos. 19‐2300, 19‐3122, & 19‐3235
terest. The court reasoned that the contract did not “ever an‐
ticipate[] a controversy of this nature” (restraint of funds in
an escrow account) so that the contract could not have waived
pre‐judgment interest. Id. at *5.
We do not disagree with Katzman, but that case differs
from this one in decisive ways. First, this contract is subject to
Illinois law, which uses only a presumption of pre‐judgment
interest in some cases, while Katzman applied New York law,
which generally requires prejudgment interest. Compare, e.g.,
Santa’s Best Craft, LLC v. Zurich American Ins. Co., 408 Ill. App.
3d 173, 191, 346 Ill. Dec. 733, 941 N.E.2d 291, 307–08 (2010)
(trial court’s decision to award pretrial interest is discretion‐
ary and subject to prudential concerns), and Kouzoukas, 234
Ill. 2d at 476, 234 Ill. Dec. at 942, 917 N.E.2d at 1017 (“Statutes
permitting the recovery of interest … must be strictly con‐
strued.”), with Katzman, 2013 WL 1496952, at *2 (“A long line
of case law has held that prejudgment interest is mandatory.”)
(collecting cases applying New York law).
Second, although the waiver provisions in the Agreement
here and the Katzman contract are similar, the overall contracts
are not. The Agreement here expressly contemplated that
funds could be held in escrow past eighteen months if Sterling
brought a Direct Claim. That’s exactly what happened. Noth‐
ing in the Agreement suggests that holding funds in escrow
because of an ongoing dispute would breach the Agreement.
That’s the point of the escrow fund. Thus, unlike in Katzman,
the parties here did “anticipate a controversy of this nature”
and excluded it from the definition of indemnifiable Losses.
The Sellers further argue that the Exclusive Remedies pro‐
vision does not apply here because Sterling’s request for in‐
demnification qualified as “intentional misconduct” in three

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Nos. 19‐2300, 19‐3122, & 19‐3235 27
ways. None is convincing. First, they claim that it was miscon‐
duct for Sterling to seek indemnification for funds it has not
yet paid to former clients. But indemnifiable “Losses” in‐
cludes “liabilities,” an ambiguous word that can refer to a case
such as this, where “society is not yet commanding perfor‐
mance, but it will so command if the possessor of the power
does some operative act.” Black’s Law Dictionary (11th ed.
2019), quoting William R. Anson, Principles of the Law of
Contract 9 (Arthur L. Corbin ed., 3d Am. Ed. 1919). The
Sellers’ reading of this provision would also present Sterling
with a Catch‐22: the Sellers say both that demanding indem‐
nification for as‐yet unpaid funds is intentional misconduct,
but also that paying refunds before an indemnification de‐
mand was a breach that caused the Sellers irrevocable harm.
Second, the Sellers claim that Sterling committed inten‐
tional misconduct in seeking attorneys’ fees. The definition of
Losses in Section 1 is internally contradictory. It both includes
and excludes attorneys’ fees: “Losses means all … out of
pocket third party costs or expenses of whatever kind, includ‐
ing reasonable attorneys’ fees … provided, however, that
‘Losses’ shall not include … attorneys’ fees and expenses.” Re‐
gardless of how this issue might ultimately be resolved, we
cannot see how arguing one side of this “classically ambigu‐
ous” contradiction could be intentional misconduct. See Uni‐
versal Guaranty Life Ins. Co. v. Coughlin, 481 F.3d 458, 464 (7th
Cir. 2007).
Third, the Sellers claim that even if hypothetical future
payments and attorneys’ fees are included, Sterling’s itemized
Losses did not add up to two million dollars, so that it was
misconduct to ask for more than Sterling would be entitled to.

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28 Nos. 19‐2300, 19‐3122, & 19‐3235
But Losses also include “the cost of enforcing any right to in‐
demnification,” which the parties have now been litigating for
four years.4
Even if the Agreement did not waive claims to pre‐judg‐
ment interest, it is not clear that the Illinois Interest Act would
apply. The Act allows for pre‐judgment interest for “money
due on a” document or “vexatious refusal to pay.” Money was
not due on the Agreement because it expressly granted Ster‐
ling the right to reserve escrow funds. Although the district
court did not directly address the “vexatious” prong, it rightly
noted that a “faulty reading” of the Agreement differs from
willful misconduct. Sterling II, 2019 WL 5085715, at *6. Re‐
gardless of who prevails at the end of this lawsuit, it is hard
to see on this record how the district court’s refusal to award
pre‐judgment interest here could be an abuse of discretion.
See Twenhafel v. State Auto Prop. & Casualty Ins. Co., 581 F.3d
625, 630–31 (7th Cir. 2009).
The conclusion that pre‐judgment interest is unavailable
here is bolstered by the fact that the Agreement explicitly re‐
quires post‐judgment interest in certain circumstances. The
parties’ choice to write around the indemnification require‐
ments for one specific exception further underscores that they
did not intend to do so for all cases. See Rickher, 535 F.3d at
668 (explaining that Illinois courts use expressio unius canon as
an interpretive tool).
Finally, we address two remaining issues that may resur‐
face on remand: the district court’s refusal to award post‐
4 We decide here that requesting attorneys’ fees as Losses did not
amount to intentional misconduct, but we do not decide here whether at‐
torneys’ fees are in fact Losses.

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Nos. 19‐2300, 19‐3122, & 19‐3235 29
judgment interest at the higher contractual rate and its award
of certain costs for duplicating electronically stored infor‐
mation.
A federal statute calls for post‐judgment interest on
money judgments at a formula tied to the market for one‐year
Treasury bills. 28 U.S.C. § 1961. The Sellers want to collect
12% post‐judgment interest based on a provision in the
Agreement imposing that higher rate where the indemnifying
party fails to make full payment within five business days of
a “final, non‐appealable adjudication.” See § 8.06(a). The dis‐
trict court correctly observed that the Agreement’s 12% inter‐
est rate does not apply until after a judgment becomes final
and non‐appealable. Again, that’s what the parties bargained
for, and that’s the rule that applies.
Regarding costs, the circuits disagree under 28 U.S.C.
§ 1920(4) about the outer boundary of reimbursable copying
costs for electronically stored information. See Colosi v. Jones
Lang LaSalle Americas, Inc., 781 F.3d 293, 297–98 (6th Cir. 2015),
discussing CBT Flint Partners, LLC v. Return Path, Inc., 737 F.3d
1320 (Fed. Cir. 2013), and Race Tires America, Inc. v. Hoosier
Racing Tire Corp., 674 F.3d 158 (3d Cir. 2012); see also United
States ex rel. Long v. GSDMIdea City, LLC, 807 F.3d 125, 131–32
(5th Cir. 2015) (“Courts have not uniformly addressed which
electronic discovery costs are recoverable under the most re‐
cent version of § 1920(4).”); but see Hecker v. Deere & Co., 556
F.3d 575, 591 (7th Cir. 2009) (concluding without elaboration
that “the costs [] for converting computer data into a readable
format … are recoverable under 28 U.S.C. § 1920”). If the par‐
ties wish to press this issue on remand, they may want to pay
close attention to these differences. Some of the requested
copying costs here may lie beyond the outer limits of some or

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30 Nos. 19‐2300, 19‐3122, & 19‐3235
all of the circuits’ tests. Compare Race Tires, 674 F.3d at 167,
citing Hecker, 556 F.3d at 591 (excluding from taxable costs
“collecting and preserving ESI; processing and indexing ESI;
[and] keyword searching of ESI for responsive and privileged
documents”), with Dkt. 176 at *59 (requesting costs for quality
control and communicating with Sellers); *63 (requesting
costs for time spent verifying password).
The judgment in favor of the Sellers is REVERSED and this
case is REMANDED for further proceedings consistent with
this opinion.

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