Photographs by Simon Dawson/Bloomberg,Scott Eells/Bloomberg

Outrageous CEO Wagers

  1. Richard Branson vs. Willie Walsh
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    Richard Branson vs. Willie Walsh

    Virgin Group CEO Richard Branson on Dec. 10 bet Willie Walsh, chief executive of British Airways owner International Consolidated Airlines Group (IAG), that Virgin would still be in business in five years. In lieu of the £1 million ($1.6 million) that Branson offered, Walsh instead wagered a “knee in the groin.” These two are not the first CEOs to put money—and dignity—on the line over a difference in opinion.

    Photographs by Simon Dawson/Bloomberg,Scott Eells/Bloomberg
  2. Leo Mullin vs. Gerald Greenwald
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    Leo Mullin vs. Gerald Greenwald

    In 1998, Leo Mullin, then-chief executive of Delta Air Lines (DAL), bet United Airlines (UAL) CEO Gerald Greenwald 1,000 basketballs, worth more than $20,000, that the Utah Jazz (which played at the Delta Center—now called EnergySolutions Arena) would beat the Chicago Bulls (of the United Center). Mullin lost and later admitted he was secretly rooting for the Bulls all along. The basketballs were donated to schools.

    Photographs by Susan Walsh/AP Photo, Emile Wamsteker/Bloomberg
  3. Sam Walton vs. David Glass
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    Sam Walton vs. David Glass

    After losing a bet to store managers and then-Chief Operating Officer David Glass that the company could not achieve a pretax profit of 8 percent, Wal-Mart (WMT) founder Sam Walton put on a grass skirt and did the hula dance on Wall Street in 1984.

    Photographs by Beth Hall/Bloomberg, John Sleezer/Kansas City Star/MCT via Getty Images
  4. Vince McMahon vs. Donald Trump
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    Vince McMahon vs. Donald Trump

    World Wrestling Entertainment (WWE) owner Vince McMahon’s chosen wrestler lost him the "Battle of the Billionaires" in 2007. Opponent Donald Trump shaved off McMahon’s hair in the ring, on live TV. Ever dramatic, McMahon screamed, "Don't do this to me!"

    Photographs by Jeff J Mitchell/Getty Images, Bob Levey/WireImage
  5. Mitt Romney vs. Ed Rendell
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    Mitt Romney vs. Ed Rendell

    Former Pennsylvania Governor Ed Rendell has made many a sports bet with politicians. For instance, after the New England Patriots beat the Philadelphia Eagles in the 2005 Super Bowl, Rendell, losing his wager with Romney, sang the national anthem with his wife before a Celtics-76ers game. At least it wasn’t America the Beautiful.

    Photographs by Brendan Smialowski/Getty Images, Daniel Acker/Bloomberg
  6. MC Hammer vs. Carl Icahn
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    MC Hammer vs. Carl Icahn

    In the 1991 Mother Goose Stakes, rapper and founder of record label Bustin' Records MC Hammer (son of a career horseplayer) made a side bet with business magnate Carl Icahn, then chief executive of TWA. Icahn's thoroughbred champion Meadow Star won and Hammer handed him a check for $35,000 "for personal advice," as he noted on the check. A month later, Hammer won $150,000 in another racing bet with Icahn.

    Photographs by Kevin Winter/Getty Images, Scott Eells/Bloomberg