Legal filings and sworn statements have dropped Honolulu broker Stephen Cipres into the middle of a high-profile scandal over consensual and allegedly coerced sexual encounters that reportedly took place inside homes he was hired to sell. The accusations, made by his former executive assistant, have triggered multiple civil lawsuits and led his local firm to cut ties. Cipres denies forcing anyone to do anything and has responded with a defamation suit of his own.
In affidavits and deposition excerpts, the assistant, Sarah Dombrose, says she and Cipres had intimate encounters at "10 to 20" listed properties between 2021 and 2024, including some meetups during normal business hours, according to Honolulu Civil Beat. Dombrose told the outlet she "felt obligated to perform oral sex on him to keep my employment" and said Cipres sometimes paid her large sums from his personal accounts. Through his attorney, Cipres has said the relationship was consensual and has alleged that Dombrose initiated some of the encounters.
Court filings and deposition material posted online, including complaint documents hosted on DocumentCloud, show that Dombrose’s estranged husband, Matthew Gillespie, sued Cipres in 2024 for intentional infliction of emotional distress and related claims. Cipres has answered with a defamation suit, setting up dueling civil cases that remain in the discovery phase.
The legal saga has moved beyond local dockets. TMZ summarized the filings on July 2 and reported that Corcoran Pacific has cut ties with Cipres, even as he continues to market properties through his own brokerage. Local reporting says Corcoran Pacific’s leadership told Cipres to resign after deposition disclosures surfaced, while the national Corcoran Group has stressed that its franchise affiliates are independently owned and operated.
Potential licensing and legal consequences
Hawaiʻi law and the Real Estate Commission’s rules require licensees to "protect the public against fraud, misrepresentation, or unethical practices" and give regulators the authority to fine, suspend or revoke licenses, according to the state commission’s bulletin. The DCCA Real Estate Bulletin and related Hawaii Administrative Rules (HAR §16-99-3) spell out the standards the commission applies. A spokesman for the Department of Commerce and Consumer Affairs told Honolulu Civil Beat that Cipres’ broker license remains valid and that the commission had not received any complaints related to the filings as of the outlet’s reporting.
What’s next in court
Both sides have filed complaints and sat for depositions, and portions of those records are publicly accessible through court filings and document repositories such as DocumentCloud. The litigation is expected to move forward through discovery, motion practice and possibly settlement talks. Any court orders or administrative findings could influence whether the Real Estate Commission launches a separate regulatory inquiry.
The controversy has also raised uncomfortable questions about brand oversight and client trust in the luxury market. Corcoran Pacific’s public profile for Cipres highlights his long-standing role in Oʻahu’s high-end real estate scene and lists active properties associated with his name, underscoring the reputational stakes for sellers, buyers and the wider local brokerage community. The company notes in its public materials that franchise affiliates operate independently. Corcoran Pacific lists Cipres’ office and active listings as part of that public record.
