James E. "Jimmy" Cayne (born February 14, 1934) is an American businessman, a former CEO of Bear Stearns and world-class 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.CNBC named Cayne as one of the "Worst American CEOs of All Time".
Cayne grew up in Evanston, Illinois. His father was a patent attorney. He is uncle to hedge fund investor Richard Cayne Perry. Cayne attended Purdue University, but he left before graduating to join the United States Army. His first job was as a traveling salesman selling photocopiers 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 C. 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.