Who

Citigroup's former chairman and CEO, Weill now tends to various philanthropic pursuits.

Backstory

Born and raised in Bensonhurst, Weill started out as an engineering student at Cornell, switching to government after nearly flunking out. He managed to graduate, though, and in 1955 he moved to New York, landing at Bear Stearns as a runner and a few years later moving up to broker with just two clients, his mother and a former boyfriend of his wife. Needless to say, things soon picked up. In 1960, Weill went into business on his own, teaming up with partners Roger Berlind, Arthur Carter (and, later, Arthur Levitt). The endeavor succeeded quickly thanks to acquisition-happy Weill, who engineered more than a dozen deals in the 1960s and '70s to create the powerhouse Shearson Loeb Rhodes. In 1981, Weill cashed out, offloading the firm to American Express for $900 million. A power struggle with Amex's James Robinson forced Weill to exit soon after—so he started all over again. With $7 million of his own money, he took over a troubled financial services company called Commercial Credit and proceeded to build yet another financial conglomerate, acquiring nearly a dozen companies over the course of a decade, including Travelers Insurance and Salomon Bros. In 1998, he formed Citigroup via a $78 billion merger with Citicorp.

Of note

Weill transformed the rules of the banking game: He helped demolish the Depression-era rules that had separated investment and commercial banking, and pioneered the notion that consumers would purchase all of their financial services from a single provider—possibly the height of his professional glory. But his inability to structure his succession—he ousted Jamie Dimon, his one-time heir apparent, and clashed with Citi's John Reed, his co-CEO—was followed by the biggest blemish of all: the scandal surrounding conflicts of interest within Citi's investment research division.

After an investigation showed that Weill had implicitly solicited a bullish rating on a stock from analyst Jack Grubman in exchange for arranging admission to the 92 Street Y's elite preschool for Grubman's twins, Weill found his reputation tarnished and his ability to run the company restrained by regulators. He resigned as CEO in 2003—Charles Prince was installed as the company's chief—and then stepped down as chairman in April 2006. Yet his influence over Citi remains formidable. In 2007, he helped negotiate the ouster of his protégé Chuck Prince following unexpectedly steep losses in connection with the subprime loan crisis, and he was supportive of the board's decision to replace Prince with Vikram Pandit.

Keeping score

Weill is estimated by Forbes to be worth $1.3 billion. He earned close to a billion dollars in cash and stock during his final five years at the helm of Citigroup.

Pet causes

Weill has pursued philanthropy as energetically as he pursued empire building over the past few years. He and his wife have funded various artistic institutions around town (reflected by the numerous facilities named in their honor) but Weill's largest gifts to date have been directed to Cornell's medical school and New York Hospital. Now named the Weill Cornell Medical College, the couple has donated an extraordinary $500 million to the center since the late 1990s, including a record-setting $250 million donation in 2007.

In print

In 2007, Weill published a memoir, The Real Deal: My Life in Business and Philanthropy. The book attracted controversy over the sharp words he reserved for some of his former colleagues and competitors, including Jack Welch and Lou Gerstner. A more balanced portrayal of Weill's legacy can be found in WSJ reporter Monica Langley's Tearing Down the Walls.

In person

Weill's taste for fine foods and alcohol—he has a particular love of Chateau Margaux—once saw him balloon to 250 pounds. (He used to belong to an exclusive wine-drinking club that hosted dinners where the members would drink up to $1 million of wine.) Weill remains an avid golfer and a member at Augusta National Golf Club, home of the Masters.

Personal

Weill is married to Joan Mosher Weill, who's currently chair of the board of the Alvin Ailey American Dance Foundation. The couple has two adult children, Marc Weill and Jessica Weill Bibliowicz. In 2007, Weill paid $42.4 million for a penthouse at 15 Central Park West. The 6,744-square-foot apartment, which has more than 2,000 square feet of terraces, is located on the 20th floor of the "Tower" building. The couple's new neighbors in the building include Dan Loeb, Bob Costas, Denzel Washington, Sting, Dan Och, and Arthur and William Zeckendorf. The Weills also have a weekend home in the Adirondacks.

Family ties

Both of Weill's children once held senior positions at Citi. (Indeed one of the reasons Jamie Dimon was forced out of Citi was because of his reluctance to promote Jessica Weill as quickly as her father would have liked.) Jessica currently serves as CEO of National Financial Partners. Marc resigned from Citi following a trip to rehab for a cocaine addiction and a widely-reported affair with an adult film actress.

No joke

Weill says he was scared of heights as a kid and only got over the phobia when he purchased his first private jet in the 1980s. Since then, flying private has been de rigueur for the finance mogul: Part of his retirement package consisted of continued access to Citi's fleet of jets until it was revealed publicly.