James Cayne
(February 14, 1934 - December 28, 2021)
James Cayne stepped down as chief executive of investment bank Bear Stearns at the beginning of 2008, the year the firm went bust. The Wall Street Journal blog said that during 10 critical days of the bank's crisis in July 2007, Cayne was playing in a bridge tournament in Nashville, Tenn., without a cell phone or an email device.
The WSJ also reported that Cayne sometimes smoked marijuana after bridge tournaments, citing interviews with attendees at the tournaments. Cayne denied one alleged incident in 2004, but when asked whether he smoked pot during bridge tournaments on other occasions, he said he would respond only "to a specific allegation."
Cayne serves as a Bear Stearns director starting in 1985. According to The New York Times, "Until the mortgage meltdown, the firm had a spectacular run under Mr. CayneÕs decade and a half of leadership, with its stock soaring from $16 to a high of $172 in 2007. With his deep appreciation for the firmÕs quirky culture, Mr. Cayne was able to carve out a respectable niche in areas like back office support for mutual and hedge funds while enhancing firmÕs expertise in bonds."
The cigar-smoking former scrap metal salesman cashed in his share of Bear Stearns for $61 million in 2008, sending their stock down 5%.
UPDATE 2026: Cayne is mentioned in the 1/4/2026 New York Times Magazine article "Scams, Schemes, Ruthless Cons: The Untold Story of How Jeffrey Epstein Got Rich," which says, "Rumors, perhaps fueled by envy, began to spread that Epstein was helping Cayne to pursue women and score drugs, according to several of their colleagues." His relationship with Cayne "really catapulted" Epstein, and the two were described as "sleazeballs."
