James Cayne

James E. "Jimmy" Cayne (February 14, 1934 – December 28, 2021) was an American businessman and CEO of Bear Stearns. In 2006, he became the first Wall Street chief to own a company stake worth more than $1 billion, Cayne attended Purdue University, but left before graduating to join the United States Army.

His first job was as a traveling salesman; he then sold scrap iron and municipal bonds. and he was with the company until its demise.

Wealth In 2005, Forbes magazine ranked him 384th among the 400 richest Americans, with an estimated net worth of $900 million. or 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 of the company. It is estimated that the value of Cayne's 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. In addition to being named on this list, Time also alleged that of all the CEOs during the crisis, "none seemed more asleep at the switch" than Cayne. They had one child, Alison Cayne Schneider. Alison is divorced from hedge fund manager Jack Schneider with whom she has five children. He was uncle to hedge fund investor Richard Cayne Perry.

Cayne had one child from his first marriage, Jennice Cayne Nienkerk, who has two daughters.

Cayne died on December 28, 2021, at the age of 87, at a hospital in Long Branch, New Jersey, from complications of a stroke.

In 2025, a copy of Jeffrey Epstein's birthday book from 2003 was released, which included a note from Cayne. The New York Times described him and Epstein as having a "close relationship".

Bridge Cayne, himself a sound bridge player, His bridge career as a sponsor and player has resulted in attaining the ranks of ACBL Grand Life Master and World Bridge Federation World Master. In the biennial Bermuda Bowl world championship teams, his 1995 team USA1—one of two that represented the United States, a unique status—finished ninth (the lowest U.S. finish in the sixty-year history of the event), while Team USA2 placed first. In March 2002, The New York Daily Sun announced that Cayne would be contributing a bridge column.