15 of the Most Astonishing Retirements, Bonuses and Cash-Outs in Corporate America

Updated: June 17, 2009

While athletes' contracts grab all the headlines, they can't hold a candle to the most legendary corporate cash-outs, retirements, and bonuses. Here are 15 of the most astonishing retirement packages, severance payouts and bonuses that corporate America has ever seen.

  1. Lee R. Raymond — Exxon Mobil Corp.: Raymond bailed in 2006 with a golden parachute that totaled more than $351 million. Raymond's biggest contribution to the petroleum powerhouse came in 1999, when he struck up the merger between Exxon and Mobil to create the largest and most profitable oil company on earth. Ever the accountable penny-pincher, Raymond has said that he will partly reimburse the company when he uses Exxon Mobil's private jet for personal use.
  2. Edward Whitacre — AT&T: Whitacre walked away in 2007 with $158.5 million after a 43-year career with the telecommunications giant. Shareholder wealth and a long tenure as the company's CEO were the reported reasons for the size of his retirement package. To sweeten the deal, AT&T will pick up the tax tab for the bulk of Whitacre's benefits, as well as provide his family with insurance for life.
  3. Richard Handler — The Jeffries Group Inc.: Not to be shown up, Handler launched into retirement with a cool $202 million package in 2007. The company told The Wall Street Journal that Handler's work in growing the share price 400 percent in his seven-year stay earned him his pretty payout. Handler is currently the chairman and CEO of the Handler Family Foundation, a nonprofit that benefits underprivileged children. He also chairs the board of trustees for his alma matter, the University of Rochester.
  4. Michael D. Eisner — Disney.: Eisner stepped down as CEO in 2005 after the media-dubbed "Disney War," in which stockholders and board members squared off against Eisner and other members of the company. His 2004 letter detailed his plans to depart the company in 2006, but due to the corporate drama, Eisner decided to cut his stay short by a year. It is estimated that Eisner accumulated over $1 billion in bonuses, salary and stock options during his 21 years at Disney.
  5. Henry A. McKinnell — Pfizer Inc. : When Henry A. McKinnell decided to throw in the towel at Pfizer in 2006, he left with a $213 million parachute with the possibility of more, contingent upon company stock. In his time as CEO, the Pfizer's stock went down 40 percent, costing shareholders $140 billion. At a company meeting held in Lincoln, Neb., a plane was seen flying over the building with a banner that read "Give It Back, Hank!"
  6. Jack Welch — General Electric Co.: Jack Welch said his goodbyes in 2002, taking a modest $9 million. Per year. For the rest of his life. This pretty little pension comes with perks like charge accounts at his favorite restaurants, use of the company plane, maid service at his multiple abodes and other parting gifts. The exact specifications of Welch's departure gift basket were murky at best, even to key shareholders, which prompted the SEC (Securities and Exchange Commission) to ask for further documentation.
  7. Charles Prince — Citigroup Inc.: Charles Prince retired with a $42 million package in 2007, contingent on the company's stock performance. Add this to his 1.61 million shares of stock, which are currently worth about $53 million, and his nest seems to be fairly feathered.
  8. Stanley O'Neal — Merrill Lynch & Co. Inc.: Stanley O'Neal retired with a solid $161.5 million in 2007. His departure was influenced by the company's loss of $2.3 billion in Q3 of that year, followed closely by a pesky $8.4 million government charge for botching credit and mortgage investments after the U.S.'s subprime mortgage crisis.
  9. Robert Nardelli — The Home Depot: Robert Nardelli decided to part ways to the tune of $210 million in cash and stocks in 2007. Nardelli was hired in 2000 to beef up company profits, and while the company's revenue and profits nearly doubled in his first five years, they fell short of his projected goals.
  10. James Kilts — The Gillette Co.: The year 2005 saw James Kilts get merged out of a job when Procter & Gamble munched up Gillette into its corporate kingdom. The now former CEO shouldn't have any hard feelings: Procter & Gamble gave him a $165 million payout full of perks and cash. Procter & Gamble was even nice enough to provide Kilts with $13 million to cover the transaction's resulting taxes, ensuring that his pockets stayed deep. In 2007, Kilts joined the Board of Directors at Pfizer.
  11. Dick Cheney — Halliburton: When his vice-presidential ticket was punched in 2000, Cheney stepped on to the White House lawn and quietly gave up his title as CEO of a little government-contracting company named of Halliburton — with a $34 million rip cord on his golden parachute. Cheney was kept on the company's payroll after retirement, however, and was paid deferred compensation for his years of service. He also retained around 430,000 shares of Halliburton stock, which eventually led to questions about his business ties to a company that seemed to have benefited quite well from the War on Terror.
  12. Angelo Mozilo — Countrywide Financial Corp.: It is never fun showing up for work if you've been labeled as the man who is responsible for a national crisis. But instead of hiding away in an undisclosed location while his public-relations people apologized, Angelo Mozilo — former CEO of Countrywide Financial — showed up and faced the music with class. As head of one of the nation's leading mortgage companies, Mozilo was at the forefront of the subprime-mortgage bubble that began to burst in 2007. Mozilo turned his back on $37.5 million in severance pay and perks, as well as a $400,000 annual salary. He instead opted to testify on the whole mess before the Congressional Committee on Oversight and Government Reform in March 2008. After the housing-loan episode, Countrywide Financial agreed to be bought by Bank of America Corp. to the tune of $4.1 billion. Don't go feeling sorry for our hero though: Mozilo's bare-bones retirement package, which he received for his years with the company, totaled around $23.8 million.
  13. Robert Toll — Toll Brothers Inc.: On the other side of the subprime-mortgage coin, some CEOs are receiving bonuses regardless of the industry's current public image. Luxury-home builder Toll Brothers Inc. announced in March 2008 that chairman and CEO Robert Toll will receive a scheduled $17.5 million bonus, along with his current 2 percent annual draw from the company's earnings before taxes.
  14. John J. Mack — Morgan Stanley: In 2006, John J. Mack received a $40 million bonus, as Morgan Stanley's stock went up 42 percent. His monetary reward set a Wall Street record as the largest bonus of its time but was promptly topped the following year.
  15. Lloyd Blankfein — The Goldman Sachs Group Inc.: Besting Mack in 2007, Lloyd Blankfein saw a $60.7 million bonus when he peeked into the envelope.
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