D'oh! E-mails that embarrass

When the history of embarrassing instant-message conversations is finally written, former Rep. Mark Foley deserves his own chapter.

The Republican politician from Florida spent a good portion of his career selling himself as a leading defender of children on the Internet. In reality, if IM transcripts posted by ABC News are accurate, Foley's favorite use of the Internet was to engage in lurid conversations about masturbation. Here's an excerpt that's almost safe for a family publication:

Maf54 (8:03:47 PM): what you wearing
Xxxxxxxxx (8:04:04 PM): normal clothes
Xxxxxxxxx (8:04:09 PM): tshirt and shorts
Maf54 (8:04:17 PM): um so a big buldge
Xxxxxxxxx (8:04:35 PM): ya
Maf54 (8:04:45 PM): um
Maf54 (8:04:58 PM): love to slip them off of you

Bill Gates now has a permanent place in business-school case studies--not only for creating Microsoft, but for careless trash-talking in e-mail.

Gates' e-mail exchanges became a highlight of the 1998 antitrust trial, which ended with a consent decree after the U.S. Department of Justice failed in its bid to break up the company. "I want to get as much mileage as possible out of our browser and Java relationship here," Gates wrote in an August 1997 internal message. "Do we have a clear plan on what we want Apple to do to undermine Sun?"

Then-U.S. District Judge Thomas Penfield Jackson used those e-mail exchanges to poke fun at Gates, calling him not "particularly responsive" when the Microsoft executive was quizzed about them during cross-examination. An appeals court later gave Jackson the boot, unanimously ruling that he had "seriously tainted the proceedings."

No wonder that U.S. Attorney General Alberto Gonzales and President Bush have forsworn e-mail. "I've made an easy decision there," Bush said last year. "I just don't do it?Everything is investigated in Washington. And that's just the nature of the way here right now. And so we're losing a lot of history, not just with me, but with other presidents, as well."

Electronic archives brought down Harry Stonecipher, once Boeing's president and chief executive. He resigned in March after reports of an extramarital affair with a female Boeing executive.

The smoking gun, in part, was sexually explicit correspondence between Stonecipher and his paramour. The Wall Street Journal reported at the time that the conversations took place at least in part through e-mail.

Would-be workplace sweethearts, be warned: Plenty of businesses monitor employees' e-mail messages, and it's perfectly legal to do so. A study that News.com wrote about last year said that 63 percent of corporations with 1,000 or more employees either employ or plan to employ staff to read or otherwise analyze outbound e-mail.

If you're a well-paid corporate lawyer, don't ask your secretary to reimburse you for a minor dry-cleaning expense. And if you must demand the cash, do not put it in e-mail.

That's what apparently cost Richard Phillips his job in the swank London offices of the Baker & MacKenzie law firm.

"I went to the dry-cleaners at lunch and they said it would cost 4 (pounds) to remove the ketchup stains," Phillips, then a 36-year-old attorney, wrote in an e-mail bearing the Subject: line "Ketchup Trousers" to his secretary, Jenny Amner. He added that it would be "much appreciated" if she could hand over the cash that day.

Nine days later, Amner shot back: "I must apologise for not getting back to you straight away but due to my mother's sudden illness, death and funeral I have had more pressing issues than your 4 (pounds). I apologise for accidentally getting a few splashes of ketchup on your trousers. Obviously your financial need as a senior associate is greater than mine as a mere secretary."

She added: "Should you feel the urgent need for the 4 (pounds), it will be on my desk this afternoon." Not long after the exchange was reported in the British media, Phillips resigned, although a law firm representative asserted that he had planned to do so anyway.

Henry Blodget, the notoriously optimistic Wall Street analyst, briefly enjoyed something akin to a cult following after predicting in 1998 that Amazon.com's stock price would skyrocket to $400 per share.

But Blodget's e-mail messages showed that he was more skeptical in private. For instance, in discussing GoTo.com, one client e-mailed Blodget and asked, "What's so interesting about Goto except banking fees????" Blodget's succinct reply was "nothin." Afterward, according to the Securities and Exchange Commission, he released a "fraudulent" report that was anything but skeptical.

Other e-mail messages that later became public showed that Merrill Lynch and Blodget published a favorable report about Internet Capital Group. But in private e-mail about the company two weeks later, Blodget wrote: "No hopeful news to relate, I'm afraid. This has been a disaster...There really are no 'operations' here to fall back on, so there really is no 'floor' to the stock...We see nothing that will turn this around near-term."

In 2003, Blodget reached a settlement with the SEC that included a $4 million payment and a permanent prohibition on working in the securities industry. Now he's a personal-finance columnist for Slate.com.

Oliver North may go down in history as the first government official snared because of incriminating information exchanged through e-mail.

Back in 1985, North was a Reagan administration official and a key figure in the Iran-Contra scandal, which involved secretly selling weapons to Iran to fund Nicaraguan rebels. The actions were illegal and North was convicted of three felony counts--which were eventually overturned on the theory that Congress had granted him limited immunity in exchange for his testimony.

What makes North a candidate for this gallery of rogues is that when the scandal broke in November 1986, he and John Poindexter began deleting more than 5,000 e-mail messages from White House computers. What they didn't seem to know is that backup tapes were kept, and investigators were able to reconstruct the correspondence. (Click here for some representative excerpts.)

Today, North is a political commentator and host of the Fox News program "War Stories."

Long before anyone ever heard of Rep. Mark Foley, there was Monica Lewinsky, a woman who to this day is best known for performing oral sex on President Clinton and owning a very special blue Gap dress.

At the time, Lewinsky was a White House intern who shared details of her Oval Office sexcapades in phone conversations with Linda Tripp. Unbeknownst to Lewinsky, Tripp was surreptitiously recording the chats. They eventually became part of independent counsel Ken Starr's investigation of Clinton--a reminder that not only e-mail and instant-message exchanges can prove highly embarrassing.

Lewinsky also sent Tripp e-mail messages discussing her affair with Clinton. One said of the commander-in-chief: "Big Creep didn't even try to call me on V-Day," referring to Valentine's Day. In another, Lewinsky expressed hope that "the creep will call and say 'Thank you for my love note. I love you. Will you run away with me?'" Excerpts have been preserved for posterity in an appendix to Starr's final report. (Click here for PDF.)

E-mail messages took center stage in a federal courtroom in Washington, D.C., earlier this year when a former Bush administration official was accused of lying about his involvement with high-powered lobbyist Jack Abramoff.

During opening statements in May, prosecutors told jurors that the government would prove David Safavian's guilt beyond a reasonable doubt by "relying largely on the defendant's own words" in electronic form. Safavian, a top General Services Administration official, oversaw federal procurement policy until September 2005, when he was arrested by the FBI.

In e-mail to a GSA ethics officer, Safavian wrote that Abramoff, who invited him on a lavish golf trip, "is a lobbyist and lawyer, but one who has no business before the GSA (he does all his work on Capitol Hill)." One issue in the case was whether Safavian legally could have accepted the free golf trip to St. Andrews, Scotland, with Abramoff, House Republicans Bob Ney and Tom DeLay, and former Christian Coalition leader Ralph Reed.

The prosecutors' gambit apparently worked. In June, a jury found Safavian guilty of lying and obstructing justice. Sentencing is scheduled for Thursday.

We may never know the extent of the corruption and graft in the United Nations' oil-for-food program, intended to feed Iraqi citizens. But U.S. investigators have charged that billions of dollars were illegally diverted to Saddam Hussein's regime. (Click here for PDF). Estimates are as high as $21 billion, and the United Nations has steadfastly refused to release even its internal audits.

Even though U.N. Secretary-General Kofi Annan has not been directly implicated in the scandal, e-mail messages have sketched an unflattering picture. For instance, the chief executive of IHC Services (a major U.N. contractor) sent e-mails passing on confidential U.N. information to another company. The chairman of IHC, Giandomenico Picco, is a U.N. undersecretary and Annan's personal representative on a U.N. project.

In March 2005, an independent inquiry committee said there wasn't sufficient evidence to show that Annan influenced a multimillion-dollar oil-for-food program contract awarded to the company that employed his son. But e-mails (click here for PDF) that surfaced a few months later cast doubt on that finding. Those messages from executives at Cotecna Inspection, the Swiss firm that employed his son Kojo, described meetings with the U.N. chief in Paris and New York not long before the oil-for-food contract was awarded. Kojo was paid $400,000 for less than two years' worth of work.

An ambiguous e-mail message interrupted the career of one of Silicon Valley's most influential investment bankers, Frank Quattrone. During the dot-com bubble of the late 1990s, Quattrone was head of Credit Suisse First Boston's technology group.

When the federal government accused Quattrone of overseeing the destruction of documents, they cited his e-mail message as evidence. According to the criminal complaint, one memo e-mailed to hundreds of employees and allegedly authorized by Quattrone advised: "We strongly suggest that before you leave for the holidays, you should catch up on file cleaning."

Even with that ambiguous wording, a jury convicted Quattrone in September 2004 of obstruction of justice, obstructing regulators, and witness tampering. But an appeals court this year overturned the verdict (click here for PDF) and ordered a new trial, saying the jury had been given "erroneous instructions."

In August, Quattrone was essentially exonerated in a deal he reached with federal prosecutors. It ends his problems with the criminal justice system and means he can return to the banking business. He's already received accolades from T.J. Rodgers, chief executive of Cypress Semiconductor, who said all along that Quattrone was competent, honest and ethical--and that prosecutors were publicity-hungry and out of control.

Remember Paris Hilton? There was a remarkable media blitz when her cell phone was hacked--it turned out to be a T-Mobile Sidekick, stuffed with contact information on Hollywood A-listers. Those included rapper Eminem, actor Vin Diesel, actress Lindsay Lohan, singers Christina Aguilera and Ashlee Simpson, and tennis players Andy Roddick and Anna Kournikova.

Of course it featured some explicit photos that soon appeared online. It also included touching-yet-telling text excerpts such as: "I think gamsy wants a little kiss / Its a gamma tradition / Gamsy is waiting." And: "Tell ken about jess trying to bone JT."

Breaking into T-Mobile's servers, where the Sidekick data is stored, happens not only to be pretty tacky but also a federal crime. The government wasn't amused: A Massachusetts teenager pleaded guilty in September 2005 and was sentenced to 11 months detention at a juvenile facility.

As for Hilton, the hotel heiress was arrested on suspicion of drunk driving last month. And, according to "Good Morning America," she's recently been barred from some of New York's hottest parties.

Enron's executives were not only responsible for the largest bankruptcy in United States history. They also unintentionally spurred the release of the largest collection of e-mail messages in history.

The Federal Energy Regulatory Commission released some 1.5 million Enron e-mail messages that it obtained during a post-collapse investigation, leading curiosity seekers to chuckle over the highlights.

The messages reinforced, for instance, Enron's close ties with the Republican Party. One from Steve Kean, an Enron executive vice president, to Enron Chairman Kenneth Lay said: "As I mentioned at the executive committee meeting, we have a number of people who either have expressed interest in serving on the transition team or who I would like to approach to serve on the transition team for Bush. We believe that a call from you to Cheney may be required." (For the record, the White House appears not to have done anything to bail out Enron during its downfall.)

Of more relevance to this photo gallery, though, is that the voluminous correspondence became known as the "Enron Email Dataset" and has been a boon to researchers interested in how e-mail is used in a real-world setting. A culled dataset is available from Carnegie Mellon University's computer science department. The University of California at Berkeley has its own Enron Email Analysis Project. There's even an attractive graphic.

Lay was found guilty of conspiracy and fraud and was scheduled to be sentenced on Oct. 23. However, he died in July.