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.

My brother William Cohan's Fortune cover story on Bear Stearns' former CEO Jimmy Cayne has many fascinating tales. (Fortune and BloggingStocks share the same parent -- Time Warner (NYSE: TWX)). I found three to be most interesting.

• Bear was brought down by Fidelity and Federated Investors - Fortune argues that Bear depended on the market for 'overnight repos' -- loans of a one-day term collateralized by securities -- for $50 billion of its working capital. Bear used 71% of its mortgages as its collateral and according to Fortune, "Bear's reliance on overnight Rep effectively gave the overnight lenders -- such as Fidelity and Federated Investors -- a vote on the firm's viability every night. And during that fateful week in mid-March, those overnight lenders voted a collective no. The result? Bear Stearns did not have enough cash on hand to meet customers' demands during the run on the bank."
• Cayne nearly died of sepsis 11 months ago - The article begins, "In the early morning hours last Sept. 11, a black Town Car pulled up to the entrance of New York-Presbyterian Hospital in Manhattan. Inside the sedan Jimmy Cayne, the CEO of Bear Stearns, was close to death."
• Ace Greenberg planned to ask Barbara Walters to marry him the day before she wed Merv Adelson - Fortune says that Bear's Ace Greenberg told Cayne that he was was dating Walters and was planning to marry her. According to Fortune Greenberg told Cayne, 'I've decided I'm going to marry Barbara Walters.' The very next day in the papers she's engaged to Merv Adelson."

For the full story, read the article.

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 Time Warner securities.

James Cayne added insult to injury has he sold his last $61 million in stock. He got slight ly more than $10 a share. When the stock traded above $170 lost year, he was a bit better off. According to MarketWatch, "Cayne and his wife sold two large blocks of more than 5.6 million Bear Stearns shares."

Cayne will take a beating for cashing out while many Bear Stearns (NYSE:BSC) employees lose their jobs in a takeover by JP Morgan (NYSE:JPM). He had been kicked out of the CEO job by his board. While he has much responsibility for the collapse of the firm, he has lost most of his fortune, and is in his seventies.

Cayne took what he could before the deal faces potential reviews by Congress. The transaction could still fall apart and take the stock to zero. Cayne will be long gone then, back to playing bridge, golfing, and allegedly smoking pot.

Dougals A. McIntyre is an editor at 247wallst.com.

At a mere $276 million, celebrity talk-show host and entertainment billionaire Oprah Winfrey could afford to buy Bear Stearns (NYSE: BSC), which closed Tuesday at $5.91 per share and keeps on climbing to over $6.50 a share in morning trading. The story alone and the associated publicity would be worth at least that. Furthermore, she could at least make an offer and demand a meeting with the Federal Reserve Board to discuss the issue.

If her offer was rejected, she would still be able to generate millions of dollars of publicity and perhaps she might want to acquire the asset, in particular if the Fed is going to protect the acquirer from potential losses. She could really become an international mogul, the likes of which has not been seen. We all know that Oprah wants to do good. She is so giving, this could be the ultimate.

I could just see the headlines: Oprah Winfrey takes on JP Morgan Chase (NYSE: JPM) and the Federal Reserve to rescue John Q. Public.

Bear Stearns Cos. (NYSE: BSC) embattled CEO Jimmy Cayne is lucky his firm reported its horrid quarterly results showing its biggest profit decline in more than a decade so soon after Ben Bernanke delighted the market through a larger-than-anticipated rate cut. Good thing too that the market reacted positively to comments made by CFO Samuel Molinaro that the worst is over though it wasn't clear when he developed his psychic abilities.

For now, investors are basking in the present sending shares of New York-based Bear are up in early afternoon including Goldman Sachs (NYSE: GS), which reported better-than-expected third-quarter results today. Lehman Brothers Holdings Inc. (NYSE: LEH), which reported strong earnings yesterday, also showed gains as did Merrill Lynch & Co. (NYSE: MER). Morgan Stanley (NYSE: MS), which disappointed investors, was a laggard.

Nonetheless, the contrasts between Bear Stearns and the rest of Wall Street are stark.

Bear Stearns Cos. (NYSE: BSC) Chief Executive Jimmy Cayne and his one-time protege Warren Spector attended the National Bridge Championship in Nashville in July just as the credit markets were starting to implode, showing how much their priorties were out of whack.

Spector, who was fired Sunday as the subprime meltdown engulfs the Wall Street bank, actually won his first national championship in the four-day competition which attracted about 5,000 people from 18 countries, according to Rick Beye, the tournament's director. Spector achieved the designation of Life Master at young age the age of 16. I guess he didn't discover girls until later.

Cayne's prowess at bridge is legendary. He's been a world-class bridge player for more than 30 years. Among his many titles are Grand Life Master, the highest rank of the American Contract Bridge League. Neither Berkshire Hathaway Inc. (NYSE: BRK.A) Chief Executive Warren Buffett nor Microsoft Corp. (NASDAQ: MSFT) Chairman Bill Gates, who are both avid bridge players, are close to being that good.

Of course, the bridge connection to the subprime meltdown will make it tougher for bridge to market itself as a game that's fun for players under 75. There is even a Web site called bridge is cool aimed at teens and there was a college competition at the tournament..

Of course, being a champion requires a single-minded persuit of excellence, but it seems like Cayne and Spector had better ways to spend their time. But if Nero fiddled while Rome burned, I guess these guys could play cards while Bear Stearns' shareholders shelled out $1 billion to rescue two collapsed hedge funds.

Bear Stearns Cos. (NYSE: BSC) Chief Executive Jimmy Cayne may soon be following his protege and bridge-playing buddy Warren Spector out of the venerable Wall Street bank.

Late Sunday, Cayne fired Spector, whom Bloomberg News says once viewed a potential successor, in a scene that must have been quite dramatic. The New York Times and The Wall Street Journal's accounts have Cayne delivering the bad news in a dimly lit office. Spector was apparently shocked, but he shouldn't have been.

The meltdown in the subprime mortgage market has rocked Bear Stearns. Two hedge funds have blown up costing investors more than $1 billion. Standard & Poor's cut its outlook on the company's A+ credit rating to negative on Friday. Bear Stearns' stock is in freefall, plunging more than 30 percent over the past three months. Cayne failed to reassure investors that things were going swimmingly even though he pointed out that the company was "solidly profitable" during June and July.

What's next for Bear Stearns? Well, the Journal argues that Wall Street has been "buzzing with speculation that the firm will need to seek a strategic investor."

If that's the case, it's hard to imagine that any big investor would do that with Cayne still running the show.