Alan "Ace" Greenberg, the executive who helped turn Bear Stearns Cos. into one of the world's biggest and most daring investment banks, died in New York on Friday at the age of 86 of complications from cancer.

Mr. 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 acolyte James Cayne. An avid card player, Mr. Greenberg liked tough-minded risk takers and found, in Mr. Cayne, a like-minded protégé.

Mr. Greenberg was raised in Oklahoma City and briefly attended the University of Oklahoma on a football scholarship. He brought an outsider's sensibility to Wall Street. While rival investment banks such as Goldman Sachs Group Inc. and J.P. Morgan fashioned themselves as white-shoe firms catering to the global elite, Bear Stearns was a scrappy upstart that often managed to out-hustle rivals on deals.

Bear Stearns nearly collapsed in March 2008 as clients grew concerned about the risky mortgage securities Bear had created, and pulled their money en masse. J.P. Morgan Chase & Co. bought the firm for $10 a share after initially striking a deal at $2.

Mr. Greenberg's death was confirmed by his son, Theodore.

Write to Michael Rapoport at Michael.Rapoport@wsj.com

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