Berkley Insurance Company v. Caraway et al

3:24-cv-00256Ilsd25.11.2025

Gesamter Gesetzestext

1
IN THE UNITED STATES DISTRICT COURT
FOR THE SOUTHERN DISTRICT OF ILLINOIS
BERKLEY INSURANCE CO., 	)
)
Plaintiff, 	)
)
vs. 	) 	Case No. 24-cv-256-DWD
)
JASON CARAWAY, 	)
WOWL TRUST TRUSTEE 	)
DEAN DEVERT, 	)
)
Defendants. 	)
MEMORANDUM AND ORDER
DUGAN, District Judge:
Defendant Jason Caraway (“Caraway”), formerly an attorney at Caraway &
Broombaugh, is currently serving a 90-month sentence for embezzling funds from both
his clients and his law firm. Before his indictment, the Wowl Trust, through Trustee Dean
Devert (the “Wowl Trust”), filed a lawsuit against Caraway alleging that he owed
$753,611.59 under a 2013 Sale Agreement and Promissory Note executed in connection
with Caraway’s purchase of a law firm.
In this declaratory judgment action, Plaintiff Berkley Insurance Company (“BIC”),
which issued a Lawyers Professional Liability Policy to Caraway (the “Policy”), seeks a
determination that it has no duty to defend or indemnify Caraway in the underlying
lawsuit filed by the Wowl Trust. Having failed to timely answer or appear, Caraway is
Case 3:24-cv-00256-DWD Document 48 Filed 11/25/25 Page 1 of 15 Page ID
#<pageID>
2
in default, 1 but the Wowl Trust has assumed the burden of establishing that its lawsuit
is covered by the policy BIC issued to Caraway.
Presently before the Court is BIC’s Motion for Summary Judgment as to the Wowl
Trust and for Default Judgment as to Caraway. (Doc. 43). For the reasons discussed
below, BIC’s Motion for Summary Judgment is GRANTED and its request for default
judgment is DENIED as MOOT.
I. 	U NDISPUTED MATERIAL F ACTS 2
A. The Underlying Lawsuit
On, February 9, 2023, the Wowl Trust filed a lawsuit against Caraway as the sole
defendant styled Wowl Trust – Trustee Dean Devert v. Jason Caraway, case number
1 On October 24, 2024, the Clerk entered a default against Wowl Trust and Caraway for failing to
answer or otherwise plead in response to BIC’s Amended Complaint. (Doc. 22). On November 5, 2024, the
Court set aside the default entered against Wowl Trust and granted it leave to file its proposed answer.
(Doc. 32). On April 2, 2025, the Court denied Caraway’s motion to vacate the default entered against him.
(Doc. 24). Caraway has not responded to the instant motion.
2 The Wowl Trust did not dispute BIC’s Statement of Material Facts. As such, those facts are
deemed admitted for purposes of summary judgment. SDIL-LR 56.1(g). Further, the Court disregards any
asserted facts that are not supported by proper citations to the record. SDIL-LR 56.1(c). See also Friend v.
Valley View Community Unit School Dist. 365U, 789 F.3d 707, 710-711 (district court did not abuse its
discretion in disregarding facts contained in statement of additional facts that were not supported by
proper citations to the record). For instance, the Wowl Trust states as follows in its statement of material
facts:
While Plaintiff claims not to have had any notice of this underlying lawsuit against
Caraway prior to July 20, 2023, it is noteworthy that Terri Harmon v. Jason Caraway, 23LA205
was filed February 24, 2023, with entries of appearances filed April 25, 2023, and April 27,
2023, and an Answer to the Complaint filed on June 1, 2023. Also, Thomas Dennis v. Jason
Caraway, 23LA205 was also filed on May 18, 2023.
(Doc. 46 ¶ 17). Aside from being unclear why activity in the referenced lawsuits is relevant to when BIC
received notice of the Wowl Trust’s lawsuit against Caraway, the factual assertions are deficient as they are
not supported by any citations to the record and will be disregarded by the Court. Additionally, the
following alleged facts are not supported by a citation to the record or are not supported by the record
cited: (1) Statement of Material Facts ¶ 1 (no citation to the record); (2) Statement of Material Facts ¶ 2,
assertion that the Sale Agreement was signed by Kolker Law Office, P.C., not supported by the record
because the Seller’s name is redacted; and (3) Statement of Material Facts ¶ 10 (no citation to the record).
Case 3:24-cv-00256-DWD Document 48 Filed 11/25/25 Page 2 of 15 Page ID
#<pageID>
3
23LA0142, in St. Clair County, Illinois (the “Underlying Lawsuit”). (Doc. 44 ¶¶ 1, 3). The
Underlying Lawsuit sought relief from Caraway based on his failure to make payments
under the terms of a Sale Agreement and Promissory Note. (Doc. 44 ¶ 4; Doc. 46 ¶ 13).
The Wowl Trust served Caraway with the complaint in the Underlying Lawsuit on
February 11, 2023. (Doc. 44 ¶ 2; Doc. 46 ¶ 12).
The Sale Agreement is a contract between an unidentified seller (redacted by the
Wowl Trust, hereinafter referred to as the “Seller”), 3 Kolker Law Offices, P.C., and
Caraway for the sale of a law firm. (Doc. 44 ¶¶ 5-7; Doc. 46 ¶ 2). The Sale Agreement was
signed on March 7, 2013 by Caraway “individually and as Incoming President of Kolker
Law Offices.” (Doc. 44 ¶ 6; Doc. 46 ¶ 2). The Seller retained liens on “cases and fees in
which the client or prospective client retained, or made contact with, [Kolker Law Offices]
or any of its attorneys prior to March 8, 2013, and those cases or files in which any legal
services were performed, or advice given, or the matter was contemplated to be a fee
producing matter by an attorney of [Kolker Law Offices] prior to March 8, 2013.” (Doc.
44 ¶ 8; Doc. 46 ¶ 3). The Sale Agreement established liens for full fees generated from
“Special Contingency Cases” and a specific percentage of fees generated from other
“Contingency” cases. (Doc. 44 ¶9; Doc. 46 ¶ 4). As part of the Sale Agreement, Caraway
3 In its statement of material facts, the Wowl Trust alleges that Kolker Law Offices, P.C. signed the
Sale Agreement as the seller and that, pursuant to the Sale Agreement, Caraway purchased the Kolker Law
Offices for the purpose of performing legal services. (Doc. 46 ¶¶ 1 and 2). As previously noted, the Wowl
Trust does not cite to any evidence in the record supporting the claim that Caraway purchased the Kolker
Law Office for the purpose of performing legal services or that the Kolker Law Offices signed the Sale
Agreement as the Seller. In its reply, BIC admits that Caraway signed the Sale Agreement individually and
as Incoming President of Kolker Law Offices but disputes that the Sale Agreement was signed by Kolker
Law Office, P.C. because the Seller’s name is redacted throughout the contract and the Seller’s signature
block is redacted.
Case 3:24-cv-00256-DWD Document 48 Filed 11/25/25 Page 3 of 15 Page ID
#<pageID>
4
and Kolker Law Offices acquired certain personal property in a building located in
Belleville, Illinois. Caraway and Kolker Law Offices also acquired business goodwill,
stock, and intangibles valued at $100,000, and the Seller agreed to lend money to Kolker
Law Offices, paid off pursuant to a promissory note. (Doc. 44 ¶ ¶ 10-12).
A Promissory Note was signed on March 7, 2013 by Caraway and Kolker Law
Offices. (Doc. 44 ¶ ¶ 13-14; Doc. 46 ¶ 5). Through the Promissory Note, Caraway and
Kolker Law Offices borrowed $280,000 from the Seller with interest accruing on the
unpaid balance until maturity at a rate of 4% per annum. (Doc. 44 ¶ 15; Doc. 46 ¶ 5). The
Promissory Note was for a term of 108 months (or 9 years), meaning it was set to mature
in March 2023. (Doc. 44 ¶ 16).
On February 5, 2023, the Seller assigned its rights under the Sale Agreement
and/or 	the 	Promissory 	Note 	to 	Wowl 	Trust. 	The 	document 	titled
“Agreement/Assignment” states that Caraway is in default and owes $753,651.59. (Doc.
44 ¶ ¶ 17-18).
In the Underlying Lawsuit, the Wowl Trust alleges as follows: Caraway failed to
make payments required under the Sale Agreement and the terms of the Promissory Note
and seeks to collect the amounts “due and owing” (Count I); Caraway knowingly lied
and defrauded creditors, including the Wowl Trust (Count II); Caraway “acted willfully
and wantonly” in stealing funds owed to the Wowl Trust (Count III); Caraway was an
attorney and fiduciary when he signed the Sale Agreement and when he received client
fees and costs referenced in the Sale Agreement and promissory Note and that his
Case 3:24-cv-00256-DWD Document 48 Filed 11/25/25 Page 4 of 15 Page ID
#<pageID>
5
conduct violated the appropriate standard of care for an attorney (Count IV). (Doc. 44 ¶
¶ 19-32).
The Court in the Underlying Lawsuit entered a default judgment against Caraway
and Caraway appealed. (Doc. 44 ¶ ¶ 33-34). In its appellate brief, the Wowl Trust states
as follows:
Defendant [Caraway] contracted to buy Kolker Law Offices in 2013 when
Christopher Kolker was selected to be an Associate Judge in Saint Clair
County, Illinois. The law practice collapsed because Defendant and his
wife, the firm’s bookkeeper, stole over one million dollars from clients and
Kolker prior to abandoning the firm in 2023. The scheme involved a course
of conduct where he embezzled, converted, stole, and misapplied money
from his clients and his firm by secretly using business funds for personal
use through a series of misrepresentations and acts of concealment.
(Doc. 44 ¶ 35).
B. Indictment and Guilty Plea
Caraway was indicted in the United States District Court for the Southern District
of Illinois for eleven counts of wire fraud. United States of America v. Jason Russel Caraway,
Case No. 3:23-cr-30148-NJR (Doc. 1). (Doc. 44 ¶ 36). On February 12, 2025, Caraway
signed a plea agreement admitting that he: (1) knowingly devised or participated in a
scheme to defraud; and (2) that he did so with intent to defraud; and (3) that the scheme
or fraud involved a materially false or fraudulent pretense, representation, or promise;
and (4) that for the purpose of carrying out the scheme, Defendant caused wire
communications to take place in the manner charged in counts l, 2, 3, 4, 5, and 9 of the
indictment. (Id. Doc. 26). (Doc. 44 ¶ 38).
Case 3:24-cv-00256-DWD Document 48 Filed 11/25/25 Page 5 of 15 Page ID
#<pageID>
6
C. Notice of the Underlying Lawsuit to BIC
Caraway reported the Underlying Lawsuit to BIC on July 20, 2023. (Doc. 44 ¶ 40;
Doc. 46 ¶ 21). July 20, 2023, was the first time BIC received notice of the Underlying
Lawsuit from any source. (Doc. 44 ¶ 41).
D. The Policy
The 	Lawyers 	Professional 	Liability 	Policy 	issued 	by 	BIC 	to 	Caraway 	&
Broombaugh, P.C. as the named insured was initially effective from June 1, 2022 to June
1, 2023. (Doc. 46 ¶ 6). 4 Pursuant to an endorsement to the Policy effective May 1, 2023,
the Policy’s expiration date was changed to May 1, 2023. (Doc. 44 ¶ 50; Doc. 46 ¶ 7; Doc.
11-1, pg. 24 (“In consideration of the premium paid for this Policy, it is understood and
agreed that effective May 01, 2023, the Declarations page of this Policy is amended as
follows: Item 2 and 7 of the Declarations is amended to read…Policy Period: From June
01, 2022 (inception date) to May 01, 2023 (expiration date)”).
Subject to conditions and exclusions, the Policy as amended by an endorsement
(titled “Amend Insuring Agreement to Remove Career Coverage”) provides coverage
pursuant to the following Insuring Agreement:
The Insurer agrees to pay on behalf of the Insured all sums in excess of the
deductible, up to the Limit of Liability, that the Insured shall become
legally obligated to pay as Damages and Claim Expenses because of a
Claim that is both first made against the Insured and reported in writing to
4 Lawyers Professional Liability Policy No. No. PLP-1499184-P7
Case 3:24-cv-00256-DWD Document 48 Filed 11/25/25 Page 6 of 15 Page ID
#<pageID>
7
the Insurer during the Policy Period, or any Extended Reporting Period, if
applicable, by reason of an act or omission in the performance of Legal
Services by the Insured or by any person for whom the Insured is legally
liable, while acting on behalf of the Named Insured and/or Predecessor
Firm for clients of the Named Insured and/or Predecessor Firm provided
that:
1. no Insured gave notice to a Prior Insurer of such Claim or a
Related Claim; and/or
2. no Insured gave notice to a Prior Insurer of any such act or
omission or Related Act or Omission; and/or
3. prior to the inception date of the first policy if continuously
renewed, or the date the Insured first became a member or employee
of the Named Insured and/or Predecessor Firm, whichever is later,
no Insured had a basis to believe that any such act or omission, or
Related Act or Omission, might reasonably be expected to be the
basis of such Claim.
(Doc. 44 ¶ 51).
The Policy provides the following with respect to Extended Reporting Periods:
As used herein, “Extended Reporting Period” means the period of time
after the end of the Policy Period for reporting Claims that are first made
against the Insured during the applicable Extended Reporting Period by
reason of an act or omission that occurred prior to the end of the Policy
Period and is otherwise covered by this Policy.
A. Automatic Extended Reporting Period
1. 	If this Policy is canceled or non-renewed by either the Insurer or by
the Named Insured, the Insurer will provide to the Named Insured
an automatic, non-cancelable 60 day Extended Reporting Period
starting at the termination of the Policy Period only if there is no
other policy or policies that would otherwise provide insurance for
such act or omission. This Automatic Extended Reporting Period
will terminate after 60 days.
2. 	The Insurer’s liability for all Claims reported during the Automatic
Extended Reporting Period shall be part of and not in addition to
the Limit of Liability for the Policy Period as set forth in the
Declarations and section II. Limit of Liability and Deductible.
B. Optional Extended Reporting Period
Case 3:24-cv-00256-DWD Document 48 Filed 11/25/25 Page 7 of 15 Page ID
#<pageID>
8
1. 	If this Policy is canceled or non-renewed by either the Insurer or
by the Named Insured, then the Named Insured shall have the
right to purchase an Optional Extended Reporting Period. Such
right must be exercised by the Named Insured within 60 days
of the termination of the Policy Period by providing:
a. 	written notice to the Insurer; and
b. 	b. with the written notice, the amount of additional
premium described below.
* * *
4. The Insurer’s liability for all Claims reported during the Optional
Extended Reporting Period shall be part of and not in addition to
the Limit of Liability for the Policy Period as set forth in the
Declarations and section II. Limit of Liability and Deductible.
(Doc. 44 ¶ 53).
Pursuant to the endorsement to the Policy effective May 1, 2023, the Policy was
modified to add the following language:
In consideration of the payment of the additional premium of [redacted], it
is understood and agreed that pursuant to section VI. 8. Optional Extended
Reporting Period of this Policy, the Named Insured has purchased an
Extended Reporting Period of 24 months, which Optional Extended
Reporting Period shall commence at 12:01 a.m. on May 1, 2023 and expire
at 12:01 a.m. on May 1, 2025. Such Optional Extended Reporting Period
applies only to Claims that are first made against the Insured during the
Optional Extended Reporting Period by reason of an act or omission that
occurred prior to the end of the Policy Period which is otherwise covered
by this Policy.
(Doc. 44 ¶ 54; Doc. 11-1, pg. 23).
The Policy defines the term “Claim” to mean the following:
Claim means a demand for money or services, including the service of suit
or the institution of any alternative dispute resolution proceeding, received
by the Insured arising out of an act or omission, including Personal Injury,
in the rendering of, or failure to render Legal Services.
(Doc. 44 ¶ 57).
Case 3:24-cv-00256-DWD Document 48 Filed 11/25/25 Page 8 of 15 Page ID
#<pageID>
9
II. 	LEGAL STANDARD
Summary judgment is proper when there is no genuine dispute as to a material
fact and the movant is entitled to judgment as a matter of law. F ED. R. C IV. P. 56(a); Med.
Protective Co. of Fort Wayne, Ind. v. Am. Int'l Specialty Lines Ins. Co., 990 F.3d 1003, 1008 (7th
Cir. 2021). Once a moving party has met its burden, the nonmoving party must go beyond
the pleadings and set forth specific facts showing there is a genuine issue for trial. F ED. R.
C IV. P. 56(c); Becker v. Tenenbaum–Hill Assocs., Inc., 914 F.2d 107, 110 (7th Cir. 1990). The
court considers the record as a whole and draws all reasonable inferences in the light
most favorable to the party opposing the motion. Green v. Carlson, 826 F.2d 647, 650 (7th
Cir. 1987); Fisher v. Transco Services–Milwaukee, Inc., 979 F.2d 1239, 1242 (7th Cir. 1992).
III. 	I NSURANCE PRINCIPLES
As a federal court siting in diversity, this Court applies state law to resolve
substantive questions. Harper v. Vigilant Ins. Co., 433 F.3d 521, 525 (7th Cir.2005). The
parties appear to agree that Illinois law applies, and thus this Court will apply the
substantive law of Illinois in addressing the pending summary judgment motion.
Under Illinois law, the primary function in construing an insurance policy is to
ascertain and give effect to the intentions of the parties as expressed by the words of the
policy. Cent. Illinois Light Co. v. Home Ins. Co., 213 Ill. 2d 141, 153 (2004). “If the words of
the policy are clear and unambiguous, they must be afforded their plain, ordinary and
popular meaning.” Connecticut Specialty Ins. Co. v. Loop Paper Recycling, Inc., 356 Ill. App.
Case 3:24-cv-00256-DWD Document 48 Filed 11/25/25 Page 9 of 15 Page ID
#<pageID>
10
3d 67, 73 (1st Dist. 2005). In construing an insurance policy, the court should refrain from
creating ambiguities where none exist. Id.
Illinois law provides that “the insurer's duty to defend arises when ‘the facts
alleged in the underlying complaint fall within, or potentially within, the policy's
provisions.’ ” Mkt. St. Bancshares, Inc. v. Fed. Ins. Co., 962 F.3d 947, 951–52 (7th Cir.
2020) (quoting Crum & Forster Managers Corp. v. Resolution Tr. Corp., 620 N.E.2d 1073, 1079
(Ill. 1993)); see also Pekin Ins. Co. v. Wilson, 930 N.E.2d 1011, 1016–17 (Ill. 2010) (“In a
declaratory judgment action such as that presented here, where the issue is whether the
insurer has a duty to defend, a court ordinarily looks first to the allegations in the
underlying complaint and compares those allegations to the relevant provisions of the
insurance policy.”). The insured bears the burden of proving that its claim falls within
the policy's coverage. Addison Ins. Co. v. Fay, 905 N.E.2d 747, 752 (Ill. 2009). Once the
insured has established coverage, the burden shifts to the insurer to prove that a
limitation or exclusion applies. Id.
An insurer's duty to defend is broader than its duty to indemnify. Pekin Ins. Co.,
930 N.E.2d at 1017 (citing Outboard Marine Corp., 607 N.E.2d 1204 (Ill. 1992)).
IV. 	DISCUSSION
A. Motion for Summary Judgment
First, BIC contends it owes no duty to defend or indemnify Caraway in the
Underlying Lawsuit because it does not arise out of the rendering of “legal Services” and
therefore is not a “Claim” within the meaning of the Policy. Second, BIC contends that,
even if the Underlying Lawsuit is a covered Claim, coverage is precluded because the
Case 3:24-cv-00256-DWD Document 48 Filed 11/25/25 Page 10 of 15 Page ID
#<pageID>
11
Claim was not reported during the Policy Period or any applicable Extended Reporting
Period. Lastly, BIC argues the Policy’s breach of contract, funds, and intentional acts
exclusions preclude coverage. The Court finds the second ground dispositive and
therefore does not reach the question of whether the Underlying Lawsuit constitutes a
covered “Claim” within the meaning of the Policy or whether the referenced exclusions
preclude coverage.
The type of policy at issue here is a claims-made policy. See
Mkt. St. Bancshares,
Inc. v. Fed. Ins. Co., 962 F.3d 947, 952 (7th Cir. 2020) (claims-made policies protect
against the risk of an injured party bringing a claim against the insured during the
covered period).5 The Insuring Agreement obligates BIC to pay Damages and Claim
Expenses only with respect to:
A Claim that is both first made against the Insured and reported in writing
to the Insurer during the Policy Period, or any Extended Reporting
Period, if applicable…by reason of an act or omission in the performance
of Legal Services…
(Doc. 11-1, pp. 7, 13) (emphasis added). Like the claims-made policy at issue in Continental
Casualty Co. v. Cuda, coverage is provided under the Policy only if the claim is made and
reported during the Policy Period (or applicable extended reporting period). 306 Ill. App.
3d 340, 349, 715 N.E.2d 663, 669 (1999).
5 “By way of background, conventional liability insurance policies or ‘occurrence’ policies ‘insure against a
negligent or other liability-causing act or omission that occurs during the policy period regardless of when
a legal claim arising out of the act or omission is made against the insured’ ... Because an occurrence policy
can expose an insurance company to indefinite future liability, companies often also offer a less expensive
option known as a ‘claims-made’ policy, which generally limits liability to claims made and reported
during the policy period.” Pac. Ins. Co. v. Eckland Consultants, Inc., No. 00 C 2140, 2001 WL 1388279, at *3
(N.D. Ill. Nov. 5, 2001) (internal citations omitted).
Case 3:24-cv-00256-DWD Document 48 Filed 11/25/25 Page 11 of 15 Page ID
#<pageID>
12
Here, the Policy Period originally ran from June 1, 2022, to June 1, 2023. However,
an endorsement effective May 1, 2023 shortened the Policy period, resulting in an
expiration date of May 1, 2023. Therefore, the Policy Period during which a claim had to
be both made and reported ended on May 1, 2023.
It is undisputed that Caraway was served with the Underlying Lawsuit on
February 11, 2023. Thus, to the extent the Underlying Lawsuit constitutes a covered Claim
within the meaning of the Policy (a matter the Court does not decide), the Claim was first
made against the insured on February 11, 2023 while the Policy Period was still in force.
Caraway did not report the Underlying Lawsuit to BIC until July 20, 2023, more than two
months after the Policy Period expired on May 1, 2023. The reporting was therefore
untimely unless an applicable extended reporting period preserved coverage for a claim
that was first made to the insured before the Policy Period ended.
The Policy provides two types of extended reporting periods: (1) an automatic 60-
day extended reporting period, and (2) an optional extended reporting period that the
insured may purchase. Neither provision assists the Wowl Trust in this case.
The Policy defines “Extended Reporting Period” as: “the period of time after the
end of the Policy Period for reporting Claims that are first made against the Insured
during the applicable Extended Reporting Period…and are otherwise covered by this
Policy.” (Doc. 11-1, pgs. 21-22) (emphasis added). The Optional Extended Reporting
Period purchased by Caraway, effective for 24 months beginning May 1, 2023, contains
materially identical language. It applies only to:
Case 3:24-cv-00256-DWD Document 48 Filed 11/25/25 Page 12 of 15 Page ID
#<pageID>
13
Claims that are first made against the Insured during the Optional
Extended Reporting Period by reason of an act or omission that occurred
prior to the end of the Policy Period which is otherwise covered by this
Policy.
(Doc. 11-1, pg. 23) (emphasis added).
The Policy’s language is unambiguous: both the automatic 60-day Extended
Reporting Period and the purchased 24-month Optional Extended Reporting Period
cover only claims that are first made against the insured after the Policy Period ends (i.e.
on or after May 2, 2023) and are reported during the respective Extended Reporting
Period windows. Claims that were first made during the Policy Period itself, such as the
Underlying Lawsuit, fall outside the scope of either Extended Reporting Period. These
provisions do not extend the reporting deadline for claims already made before the Policy
expired; they solely create a limited grace period for newly arising claims.
Because the Underlying Lawsuit was first made against Caraway while the Policy
was still in force, the Extended Reporting Periods provide no additional reporting
window. The Wowl Trust cannot rewrite the clear, negotiated terms of the Policy to
obtain 	coverage 	the 	parties 	never 	bargained 	for. 	Accordingly, 	neither 	Extended
Reporting Period applies here.
The Court rejects the Wowl Trust’s contention that the Policy is ambiguous or
silent with respect to reporting obligations when the Policy Period is shortened by
endorsement. (Doc. 46, pg. 8). The May 1, 2023 endorsement unambiguously established
May 1, 2023 as the expiration date of the Policy Period, and the Policy plainly required
that a claim first made during that Policy Period be reported to BIC during the same
Case 3:24-cv-00256-DWD Document 48 Filed 11/25/25 Page 13 of 15 Page ID
#<pageID>
14
Policy Period. The Wowl Trust does not point to any provision of the Policy that creates
or suggests a grace period or equitable exception when the Policy Period’s expiration date
is advanced.
The Court likewise rejects the Wowl Trust’s argument that summary judgment is
precluded because BIC cannot demonstrate prejudice from the late notice. (Id). It is well
established that, with respect to claims-made policies, timely reporting within the policy
period (or an applicable extended reporting period) is a condition precedent to coverage,
and the insurer need not prove that it was prejudiced by untimely notice. See Hanover Ins.
Co. v. R.W. Dunteman Co., 446 F. Supp. 3d 336, 348 (N.D. Ill. 2020) (“Courts strictly
construe notice requirements in claims-made policies and view notice requirements as
valid conditions precedent.”); Executive Risk Indem., Inc. v. Chartered Benefit Servs., Inc.,
No. 03 C 3224, 2005 WL 1838433, at *6 (N.D. Ill. July 29, 2005) (“Given the purpose and
function 	of 	the 	reporting 	requirement 	in 	a 	claims-made 	policy, 	such 	reporting
requirements are strictly construed.”); Pacific Ins. Co. v. Eckland Consultants, Inc., No. 00 C
2140, 2001 WL 1388279, at *3 (N.D. Ill. Nov. 5, 2001) (unlike occurrence policies, “Illinois
law is clear that the issue of prejudice is irrelevant in the context of a ‘claims-made’
insurance policy”).
Because the Claim (the Underlying Lawsuit) was first made against Caraway on
February 11, 2023, during the Policy Period, coverage required that it be reported no later
than the Policy Period’s termination date of May 1, 2023. The Automatic Extended
Reporting Period and the Optional Extended Reporting Period provide no refuge for a
claim made before the Policy Period ended. Because notice was untimely, BIC is entitled
Case 3:24-cv-00256-DWD Document 48 Filed 11/25/25 Page 14 of 15 Page ID
#<pageID>
15
to judgment as a matter of law and a declaration that it has no duty to defend or
indemnify Caraway in the Underlying Lawsuit.
B. Motion for Default Judgment
In requesting default judgment against Caraway, BIC seeks a declaration that it
owes no duty to defend or indemnify Caraway in the Underlying Lawsuit. As the Court
has decided this case on the merits in BIC’s favor in finding that, because notice was
untimely, BIC owes no duty to defend or indemnify Caraway in the Underlying Lawsuit,
BIC’s Motion for Default Judgment will be denied as MOOT.
V. 	CONCLUSION
For the foregoing reasons, summary judgment is GRANTED in favor of Berkley
Insurance Company the Court DECLARES as follows:
Berkley Insurance Company owes no duty to defend or indemnify under
the Lawyers Professional Liability Policy No. PLP-1499184-P7 with respect
to the underlying lawsuit filed by the Wowl Trust against Caraway, styled
Wowl Trust – Trustee Dean Devert v. Jason Caraway, case number 23LA0142,
previously pending in the Circuit Court for the Twentieth Judicial Circuit
in St. Clair County, Illinois.
Berkley’s request for default judgment as to Jason Caraway is DENIED as MOOT.
The Court DIRECTS the Clerk to close the case and to enter judgment accordingly.
SO ORDERED.
Dated: November 25, 2025
/s/ David W. Dugan
DAVID W. DUGAN
United States District Judge
Case 3:24-cv-00256-DWD Document 48 Filed 11/25/25 Page 15 of 15 Page ID
#<pageID>

Setzen Sie Ihre Recherche in ChatGPT oder Claude fort

Verbinden Sie Omnilex, um den Rechtskorpus über Ihren KI-Assistenten zu durchsuchen.