James E. (Jimmy) Cayne (born February 14, 1934) is an American businessman, a former CEO of Bear Stearns (1993–2008), and bridge player. After losing about one billion dollars in net worth from the collapse of Bear Stearns' stock, he sold his entire stake in the company for 61 million US$. CNBC named Cayne as one of the "Worst American CEOs of All Time".
His first job was as a traveling salesman selling copiers in the Midwest. He subsequently sold scrap iron and municipal bonds. In 1969, in New York City, he was playing bridge full time when fellow bridge-player Alan Greenberg, then a relative novice, hired him as a stockbroker at Bear Stearns; he was with that company until its demise. Cayne became president in 1985, CEO in 1993, and (while continuing as CEO) the chairman of the board in 2001.
In July 2007, Cayne was absent from New York at a bridge tournament when Bear Stearns' hedge funds collapsed. This event was one of the early signals of the subsequent global financial credit crisis. In March 2008, as Bear Stearns was on the verge of bankruptcy, Cayne played bridge at a tournament in Detroit.
On March 14, 2008, Charlie Gasparino of CNBC reported that the value of Cayne's holdings in Bear Stearns had declined from $993 million to significantly less than $200 million in the wake of Bear Stearns liquidity crisis. Just days later Bear Stearns came to agreement with competitor JP Morgan for a full buyout at only $2 share, roughly $236 million for the entire firm. At the time, Cayne had significant exposure to the company's stock, with most of his net worth tied up in shares that he had not yet exercised. It is estimated that the value of Caynes' holdings had dropped to less than $15 million as a result, effectively removing him from the list of the wealthiest individuals in the country. On March 27, 2008, it was announced that Cayne sold his entire stake in Bear Stearns, over 5.61 million shares, for $10.82 a share. This stake was sold prior to the vote on the renewed bid by JP Morgan for Bear Stearns.
Cayne is a world-class bridge player, having won more than a dozen North American championships, most recently the Reisinger Board-a-Match Teams (one of the major North American bridge championships) in November, 2007. He is ACBL Grand Life Master and World Bridge Federation World Master, and has represented the United States in the Bermuda Bowl world championship in 1995. His fellow bridge enthusiasts claim that Cayne sometimes smokes marijuana at the end of tournament sessions.
In March 2002, The New York Daily Sun, a new daily newspaper, announced that he would be writing a bridge column for the paper.
In 2005, Forbes magazine ranked him as the 384th among the 400 richest Americans, with an estimated net worth of $900 million. He is married and has two children. On February 15, 2008, the Caynes purchased two fourteenth-floor condominium units in Plaza Hotel overlooking Central Park in New York for $27.4 million. Cayne is also a veteran of the United States Army.
In the last minutes in the sale of Bear Stearns to J.P. Morgan, Cayne was competing in a bridge tournament in Nashville and was unreachable by email or cell phone, a fact for which he received much criticism.