Best & Worst in Money 2008: Biggest fall from grace

This post is part of AOL Money & Finance's Best & Worst in Money 2008 feature.

In 2008, many big names took big face plants. Since this is a blog about money, I ranked them based on how much they lost and how far they fell. As you can see, the method is not exactly scientific. Here are the five biggest falls from grace:

1. Richard Fuld, Lehman Brothers. The $639 billion bankruptcy is history's largest so far by a factor of at least six. And Fuld personally lost about $1 billion in his personal holdings of Lehman stock. And the repercussions of letting Lehman fail stretched from money market funds to Iceland. Ouch!
2. Jimmy Cayne, Bear Stearns CEO. Cayne lost plenty of his personal wealth when Bear Stearns stock stumbled. But at least shareholders were able to get out with something when JPMorgan Chase (NYSE: JPM) bought it.
3. Eliot Spitzer, New York governor. Spitzer destroyed his once promising political career by spending time with at least one woman other than his wife. He was trying to use his prosecution of Wall Street to boost his political career as Rudy Giuliani did. But his self-destructive urges got the better of him.
4. Sheldon Adelson, CEO, Las Vegas Sands (NYSE: LVS). Adelson, a colorful character who was a consulting client of mine, has lost $30 billion on paper thanks to his excessive debt load and a decline in gambling.
5. Jerry Yang, CEO, Yahoo! (NASDAQ: YHOO). Poor Jerry Yang suffered from delusions about his ability to revive his creation. He lost a chance to boost shareholder returns by selling to Microsoft Corp. (NASDAQ: MSFT) for $31 a share. With the stock at $11.51, he left big bucks on the table, and the board kicked him out of the big chair.

Let us know which one you would chose as the biggest fall of 2008.

Peter Cohan is president of Peter S. Cohan & Associates. He also teaches management at Babson College and edits The Cohan Letter. He has no financial interest in the securities mentioned.

Share the reasons for your Biggest Fall from Grace pick in the comments, or let us know about any contenders we overlooked. Also be sure to see the rest of the Best & Worst in Money 2008.