Alan "Ace" Greenberg, the executive who helped turn Bear Stearns into one of the world's biggest—and riskiest—securities firms, died of complications from cancer in New York on Friday at the age of 86.

Greenberg began his career at Bear Stearns in 1949 and rose through the ranks over many decades, taking over as chief executive in 1978 and running the New York firm until 1993, when he handed the reins to trusted associate James Cayne. An avid bridge player, Greenberg liked risk takers and found, in Cayne, a like-minded protégé.