21. Sandy Weill

Banker and Wall Street dealmaker

Benjamin Wachenje
"Learn how to be a loser, because it's important to be a loser to be a winner."

Financier and philanthropist, former chairman and CEO, Citigroup
Born: March 16, 1933, New York City
Education: Bachelor's in government, Cornell University

Sandy Weill was arguably the financial industry's master dealmaker of his time. His triumph was to have built two financial services empires like no others at the time—one, Shearson, a giant; the other, Citigroup, a colossus. His tragedy is that both would be brought low as he watched from afar.

Citigroup was intended to be the crowning accomplishment of Weill's half-century of dealmaking on Wall Street. Through mergers and acquisitions, he built the first financial supermarket since the Depression-era Glass-Steagall Act walled off banks from other financial institutions, such as securities firms and insurers. At the heart of his creation was America's largest bank.

The global financial crisis of 2008 unmasked Citigroup as an unmanageable—or, as Weill would later accuse his successors, unmanaged—corporation, devoid of the business synergies his dealmaking was meant to have enabled, and incapable of integrating its global businesses or of keeping tabs on risky investments and the staff making them.

Citi's stock fell from a high of $55 a share in 2007 to about $1 in 2009. The U.S. government stepped in with a $45 billion taxpayer bailout, and the company set about disassembling what Weill had built.

He retired as chairman of Citi in 2006, and the subprime mortgage market collapsed late in the summer of 2007. He had stepped down as CEO in 2003 in a wave of managerial restructuring that followed the stock market slump of 2002. Weill still owned 16 million shares of Citi stock, though, and tried to return in 2007 when CEO Chuck Prince, who had let its balance sheet balloon, resigned.

It might have been different had Weill not fallen out with his protégé Jamie Dimon, who as CEO of JPMorgan Chase found the synergies and management controls that eluded Citi, and steered it relatively unscathed through the financial crisis. Their 15-year partnership had ended in 1999, with Dimon being shown the door.

A falling out between Weill, then CEO of American Express, and Chairman James Robinson III in 1985 had set Weill and the young Dimon on the road to building Citi. Weill bought Commercial Credit, the troubled consumer finance arm of Control Data, for $7 million, and then began absorbing a blue-chip roster of Wall Street names: Shearson, Smith Barney and Salomon. The final piece was a $76 billion merger with Travelers Group, which closed in 1998.

Weill had been a dealmaker for a long time by then, having turned a small brokerage firm he co-founded in 1960, Carter Berlind Potoma & Weill, into Shearson Loeb Rhoades. Shearson was the second-largest securities firm on Wall Street, behind Merrill Lynch, when he sold it to American Express in 1981 for $930 million.

Though Weill became the company's president, the 1984 acquisition of investment bank Lehman Brothers quashed his ambition of becoming CEO. Lehman's Lewis Glucksman eventually got the job, and Weill was gone within a year. As it happened, he got Shearson back when AmEx began to dismantle in the early 1990s.

Speaking in 2012, Weill surprised everyone when he called for the breakup of big banks and the return of Glass-Steagall, given how aggressively he had lobbied for its repeal when creating Citi, enlisting former President Gerald Ford and former Treasury Secretary Robert Rubin to the cause. Last year he qualified his statements, saying that big banks could remain intact if "the right regulation" were in place and that they should only split up if they see it as in their own best interest.

Now in his 80s, Weill and his wife of more than 50 years, Joan, split their time between a vineyard home in Sonoma, Calif., which they bought in 2010, and their native New York. The couple are active philanthropists and fundraisers, including for Weill's alma mater, Cornell, and for Carnegie Hall.

"Philanthropy is much more than just writing a check," they wrote in an op-ed for CNBC. "It's donating your time, energy, experience and intellect to the causes and organizations you are passionate about."

Sandy Weill: Lifelong highlights

  • Started his Wall Street career as a runner for Bear Stearns in 1955, delivering brokerage orders to a floor trader
  • Owns a wood etching of himself engraved with the words "The Shatterer of Glass-Steagall"
  • Sold penthouse, on Central Park West, for $88 million in 2012, the highest home sale price recorded in New York at the time
  • Endowed Cornell University's medical school, now known as the Weill Cornell Medical College, and its Weill Institute for Cell and Molecular Biology
  • Serves as chairman of Carnegie Hall and is an enthusiastic supporter of classical music

Read MoreFULL LIST: CNBC FIRST 25

Latest Special Reports

  • Alibaba Group headquarters in Hangzhou, China

    In-depth coverage on Alibaba's IPO, including roadshow coverage, expert analysis, and Alibaba's stock price.

  • With more than 1,600 ETFs now on the market, learn more about how advisors and investors are profiting from the ETF boom.

  • Unlock the keys to building a successful long-term financial plan: manage your money, grow your money, and protect it.