By Michael Siconolfi and Michael Rapoport 

Alan "Ace" Greenberg, the executive who helped turn Bear Stearns Cos. 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.

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 associate James Cayne. An avid bridge player, Mr. Greenberg liked 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 became a symbol of the financial crisis when it 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 New York firm for $10 a share after initially striking a deal at $2.

In addition to serving as CEO, Mr. Greenberg was Bear Stearns' chairman of the board from 1985 through 2001. After that, he served as chairman of the firm's executive committee until Bear was acquired by J.P. Morgan in 2008. Mr. Greenberg told associates he was angry at how loosely the firm had been run in its later years.

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

For years, Mr. Greenberg reflected the securities firm's outcast culture on Wall Street. Rather than seek Ivy League talent, Mr. Greenberg looked for what he called "PSDs"--poor, smart employees with a deep desire to get rich. He often hired people who were fired from rival firms.

A legendary trader, Mr. Greenberg was fanatical about having static or losing trading positions sold--quickly. For years, he led what Bear Stearns called "cold-sweat" meetings in which he would grill traders on their positions. The firm printed an "aged-position report" that showed "stale" trades not sold within 90 days. He recalled that his father, a clothing retailer, often told him: "If something isn't moving, sell it today because tomorrow it will be worth less."

At a key risk meeting during the financial crisis, Mr. Greenberg had reviewed a number of the firm's negative stock bets, and wasn't happy. The positions were too risky, he warned, and should be closed out immediately. He also wanted the firm's heavy inventory of mortgage securities slashed. "We've got to cut!" Mr. Greenberg demanded.

Mr. Greenberg helped hire "ferrets," or trading police. With nicknames like "snoop" and "the hawk," these employees would scrutinize trading records. When the ferrets helped nab a Bear trader who had allegedly mismarked an options position and tried to cover it up, Mr. Greenberg fired him on the spot. "The definition of a good trader is a guy who takes losses," Mr. Greenberg said. "The definition of an ex-trader is one who tries to cover up a loss."

Mr. Greenberg urged traders and others to take calculated risks. If you haven't taken losses recently, he told traders, you haven't been taking enough risk.

Mr. Greenberg broke the tension on Black Monday in 1987 by getting up from his chair on the trading floor, practicing his golf swing and loudly announcing he was taking the next day off--even though he didn't play golf and came in the following day. Despite a $96 million loss in the crash, he said: "I wanted to show that there was no panic at Bear Stearns."

Amid the turmoil of the financial crisis, Mr. Greenberg, wearing his trademark bow tie, performed magic tricks to amuse colleagues.

He didn't like long conversations. At his desk on Bear's trading floor, Mr. Greenberg once answered a phone call from a Bear trader, paused, then barked: "Who's buying it? A client? Are you making anything off it? We can't make a living making a 16th of a point." Then he hung up.

Mr. Greenberg was one of Wall Street's quirkier characters. He was as well known for his voluminous memos and expertise outside Wall Street as his trading acumen. In 1988, he printed a bound, 50-page booklet of his memos, "Memos from the Chairman." Of the more than 100 memos he wrote between 1977 and 1993, nearly half concerned controlling costs.

His most famous memo was about expenses. The message: Stop buying paper clips.

"All of us receive documents every day with paper clips on them," he wrote. "If we save these paper clips, we will not only have enough for our own use, but we will also, in a short time, be awash in the little critters. Periodically, we will collect excess paper clips and sell them (since the cost to us is zero, the Arbitrage Department tells me the return on capital will be above average)."

He found all kinds of ways to cut costs. At a junk-bond conference at the Waldorf-Astoria once, some Bear executives wanted Aretha Franklin to sing. But Mr. Greenberg thought she was too expensive; the firm settled for the Temptations.

A Bear executive once returned with Mr. Greenberg to New York from a trip to Mexico and called his secretary to arrange a car to pick them up at Kennedy Airport. "My secretary ordered you a car," the executive told Mr. Greenberg. "Why?" Mr. Greenberg responded. "Are the yellow cabs on strike?"

Warren Buffett, the billionaire investor, once said that Mr. Greenberg "does almost everything better than I do--bridge, magic tricks, dog training, arbitrage --all the important things in life."

Mr. Buffett, who was traveling on Friday, said in a brief statement that Mr. Greenberg was "a wonderful friend and always fun to be with."

Lisa Schwartz

and Anupreeta Das contributed to this article.

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

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