In Pictures: Top 10 Smoking-Gun E-Mails

Bill Detamore has seen plenty of smoking-gun e-mails as chief legal officer of IE Discovery, an Austin, Texas-based consulting firm that helps companies search through millions of electronic documents looking for evidence that could win--or torpedo--a case. Fortunately for prosecutors and hungry plaintiff lawyers, there are usually plenty. "When you're writing e-mails, you're not thinking about how a jury will take it," says Detamore. "Even sophisticated executives do it." Here's Detamore's list of the top 10 smoking-gun e-mails:

Bear Stearns

"...the entire subprime market is toast." This unwise, if frank, observation by former Bear Stearns executive Matthew Tannin came as he and his boss were assuring investors that the subprime funds they ran were still sound. Both were indicted for fraud June 19.

Microsoft

"Winning Internet browser share is a very, very important goal for us." Bill Gates may have been stating the obvious in this 1996 directive to subordinates, but superlawyer David Boies used this and scores of other incriminating e-mails to convince a federal judge Microsoft had conspired to drive Netscape out of the business.

Chevron

American Home Products

"Do I have to look forward to spending my waning years writing checks to fat people with a silly lung problem?" This e-mail from an American Home Products executive, discovered by plaintiff lawyers and leaked to the press, helped drive a $20 billion settlement of fen-phen claims.

Merck

"I just can't wait to be the one to present those results to senior management," said an angry Merck scientist, Dr. Alise Reicin, in a 1997 e-mail after cardiovascular symptoms emerged with Vioxx. Ultimate tab to settle the litigation: $5 billion and counting.

Arthur Andersen

"Remind the engagement team of our documentation and retention policy." Arthur Andersen lawyer Nancy Temple's e-mailed instructions to the Enron auditing team preceded an orgy of document destruction and helped to seal Andersen's fate.

Credit Suisse First Boston

"Time to clean up those files." In a similar vein, former Credit Suisse First Boston banker Frank Quattrone was convicted of obstruction of justice in 2004 for allegedly instructing employees to thwart a Securities and Exchange Commission investigation with this e-mail. The conviction was reversed on appeal.

Marsh & McClennan

"I will give you clear direction on who (we) are steering business to and ... who we are steering business from." This 2002 e-mail from a top Marsh & McClennan executive helped former N.Y. Attorney General Eliot Spitzer make the case the insurance broker was engaged in a massive bid-rigging scheme.

Former Houston District Attorney

"The very next time I see you, I want to kiss you behind your right ear." One of the few printable e-mails from former Houston District Attorney Chuck Rosenthal, who resigned this year after this e-mail to his secretary and hundreds of others emerged in an unrelated civil rights suit.

Former Detroit Mayor

"Never busted. Busted is what you see! LOL." Detroit Mayor Kwame Kilpatrick was confident his affair with a city official was secret when he sent this text message. He was later indicted for denying the affair under oath.

I am a senior editor at Forbes, covering legal affairs, corporate finance, macroeconomics and the occasional sailing story. I was the Southwest Bureau manager for Forbes in Houston from 1999 to 2003, when I returned home to Connecticut for a Knight fellowship at Yale Law Sch...