Inside Josh Flagg’s exit from Douglas Elliman

Exit came in conjunction with settlement over Pasadena deal

Josh Flagg’s Elliman Exit
Josh Flagg (Illustration by Kevin Rebong for The Real Deal with Getty)

When Josh Flagg left Douglas Elliman for Compass earlier this year, all was painted rosy. Flagg called his Elliman colleagues “family,” while Elliman wished him well. 

The reality of Flagg’s exit was allegedly more contentious. 

Douglas Elliman terminated Flagg’s contract on March 11, according to documents obtained by The Real Deal pertaining to Flagg’s exit. But Douglas Elliman and Flagg disagreed on the reason for the termination. 

“My client was approached to work with Compass months before the public announcement was made that he was joining Compass in March 2024, and long before any dispute existed between Josh Flagg and Douglas Elliman,” Marty Singer, an attorney for Josh Flagg, said in a statement. “The dispute was amicably resolved.”

Flagg’s departure happened in conjunction with settlement agreements around the sale of 375 Linda Vista Avenue in Pasadena, according to emails discussing Flagg’s exit and the agreements, which were reviewed by TRD. The home sold for $4.7 million at the end of February, records show. 

Flagg had represented the seller and buyer of 375 Linda Vista Avenue, according to listings for the property. But the sellers allegedly had concerns over the way Flagg worked the sale, including whether all offers had been presented. California law requires agents present all offers to sellers, unless the seller waives that right in writing. 

To resolve any concerns, Flagg agreed to hand over his sellers’ commission on 375 Linda Vista, according to emails discussing an early version of an agreement to settle claims over 375 Linda Vista. In exchange, the sellers agreed not to bring any claims against Flagg, according to emails discussing Flagg’s exit reviewed by TRD

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The sellers, Timothy and Holly Larsen, declined to comment.

“My client did not engage in any wrongful or improper conduct in relation to the sale of the property in Pasadena,” Singer said in a statement. “There is documentation confirming that all offers for the property were communicated to the seller. Any implication or insinuation that my client did anything wrong in connection with this transaction is absolutely false and highly defamatory.”

“Josh Flagg is no longer with Douglas Elliman,” a representative for Douglas Elliman said in a statement, but declined to comment further. “We wish him the very best.”

The day after Flagg’s contract was terminated, Compass announced Flagg had joined the brokerage. In a statement, a Compass spokesperson said the brokerage had been in “discussions” with Flagg “several months prior to that date.” 

When Flagg moved, he brought a number of listings and pending deals from Douglas Elliman to Compass as part of his exit, according to the documents obtained by TRD

“My client walked away from Douglas Elliman with all of his listings worth millions of dollars, and the right to commission pending deals in escrow,” Singer said in a statement. “A real estate agent who is terminated from a brokerage does not get to take active listings or receive commission on pending deals. The listings always stay with the brokerage the agent is leaving.”

Flagg, who has starred on the Bravo show “Million Dollar Listing: Los Angeles” since 2006, joined Douglas Elliman in 2021 from Rodeo Realty, a Beverly Hills-based brokerage. 

Harrison Connery contributed reporting.