Berkley Insurance Co. v. Jason Caraway, Wowl Trust Trustee Dean Devert

CourtDistrict Court, S.D. Illinois
DecidedNovember 25, 2025
Docket3:24-cv-00256
StatusUnknown

This text of Berkley Insurance Co. v. Jason Caraway, Wowl Trust Trustee Dean Devert (Berkley Insurance Co. v. Jason Caraway, Wowl Trust Trustee Dean Devert) is published on Counsel Stack Legal Research, covering District Court, S.D. Illinois primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

Bluebook
Berkley Insurance Co. v. Jason Caraway, Wowl Trust Trustee Dean Devert, (S.D. Ill. 2025).

Opinion

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 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. UNDISPUTED MATERIAL FACTS2

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). 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. 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

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Bluebook (online)
Berkley Insurance Co. v. Jason Caraway, Wowl Trust Trustee Dean Devert, Counsel Stack Legal Research, https://law.counselstack.com/opinion/berkley-insurance-co-v-jason-caraway-wowl-trust-trustee-dean-devert-ilsd-2025.