Cypress Creek Intermediaries, Inc. v. Westport Insurance Corp.

Background

Cypress Creek Intermediaries, Inc. claimed that it helped connect Westport Insurance Corp. with TMS, Re, Inc. for a potential acquisition. Cypress Creek’s president, Andrew Pyle, contacted Westport’s Katie McGrath, arranged an introductory call involving Cypress Creek, Westport, and TMS, and helped prepare proposed nondisclosure agreements. Westport and TMS later resumed discussions without Cypress Creek’s participation, and a Westport company acquired TMS in December 2021.

Cypress Creek originally asserted claims for breach of contract, breach of the duty of good faith and fair dealing, fraud, unfair and deceptive practices under Massachusetts law, unjust enrichment, and payment for the reasonable value of its services. In an earlier order, the court dismissed the first four categories of claims but allowed the unjust-enrichment and service-payment claims to continue. Westport then moved for summary judgment under Federal Rule of Civil Procedure 56, arguing that Cypress Creek could not prove essential elements of those remaining claims.

Court’s Analysis

Under New York law, unjust enrichment and payment for the reasonable value of services are treated together as a single type of claim based on an obligation to pay reasonable compensation. The court explained that such a claim generally requires evidence that the plaintiff provided services in good faith, the defendant accepted them, the plaintiff expected compensation, and the services had a reasonable value. Unjust enrichment also requires a benefit to the defendant at the plaintiff’s expense that fairness does not permit the defendant to retain.

The court first considered New York’s Statute of Frauds, which requires certain agreements to be supported by a signed writing, including agreements to pay for negotiating a business opportunity. The court concluded that the parties’ emails and proposed nondisclosure agreements could collectively provide sufficient written evidence that Westport accepted Cypress Creek’s services. The writings included Westport’s interest in the opportunity Cypress Creek presented, Westport’s participation in the introductory call, an agreement to recognize Cypress Creek in a proposed agreement, and later discussions about Cypress Creek’s role and compensation. Because the writings and the parties’ conduct could support Cypress Creek’s position, the court found a genuine dispute of material fact rather than a basis for summary judgment.

The court next addressed whether Westport and Cypress Creek reasonably expected that Westport would owe Cypress Creek a fee. Westport argued that Cypress Creek raised compensation only after the introductory call and that it was unclear whether Westport or TMS would pay. The court found evidence pointing in both directions, including Pyle’s testimony that he discussed compensation around the time of the call, McGrath’s statement that the parties were not yet ready to discuss specifics, internal Westport communications about how Pyle would be paid, and the continuing treatment of compensation as an unresolved issue. The uncertainty about who would pay also created a factual dispute.

Finally, the court considered the reasonable value of Cypress Creek’s services. Cypress Creek proposed compensation based on 1% to 2% of certain premiums, while Westport argued that the proposed measure was unsupported and that acquisition-related compensation would ordinarily be based on the purchase price. The court held that a factfinder could determine whether Cypress Creek’s proposed fee was reasonable in these circumstances.

Disposition

Judge Edgardo Ramos denied Westport’s motion for summary judgment. The court did not enter judgment for either party on the remaining unjust-enrichment and service-payment claims. It directed the parties to appear for a conference on October 15, 2025, and directed the clerk to terminate the motions identified in the order.