All three said they halted the practice years ago. The investigation was conducted by the U.S. Attorney for eastern Missouri, Catherine Hanaway's office, along with the IRS and the FBI, dates to 2000 and negotiations have been ongoing for the last 12 to 18 months.

"This is a very profitable business that had a lot of money to spend on marketing," Hanaway said of the online gambling firms advertising on the Web. "I do think it will have a major impact. Obviously these are three of the largest online organizations in the world."

Microsoft agreed to a $21 million settlement. The company will forfeit $4.5 million, provide $7.5 million to the International Center for Missing and Exploited Children, and provide $9 million in public service ads over a three-year period starting next year. The public service campaign will be aimed at informing users, especially those college age and younger, that online gambling is illegal.

Microsoft said in a statement that it stopped accepting ads from sites associated with online gambling nearly four years ago, and "this agreement reflects our ongoing commitment to online safety. ... We're hopeful that our educational campaign will stop young people from gambling before they start."

Yahoo's $7.5 million settlement includes a $3 million forfeiture and $4.5 million in public service ads over a three-year period.
"Yahoo stopped accepting online gambling advertisements years ago, and after the U.S. Attorney's office contacted Yahoo with its concerns, we worked cooperatively over several years to reach this settlement," spokeswoman Kelley Benander said in a statement.

The settlement with Google calls for the company to pay $3 million. Spokesman Jon Murchinson said the ads appeared on sponsored links on Google.com and network sites. "While we did not admit any wrongdoing, the Department of Justice has advised that online gambling is illegal in the United States and ads to promote it are improper," Murchinson said in a statement. "Google voluntarily discontinued running such ads, which were a very small part of our AdWords business, in April 2004."

The U.S. Attorney's office here has been at the forefront of efforts to halt illegal Web-based gambling, an industry that generates about $6 billion annually in the U.S., but one that violates the Federal Wire Wager Act among other federal laws.

Earlier this year, the London-based Internet gambling firm BetOnSports PLC pleaded guilty in St. Louis to federal racketeering charges. Cases are still pending against company executives. Hanaway's office also settled a civil case against BetOnSports in November 2006. That settlement prohibits the company from accepting any bets from gamblers in the U.S.

The investigations of Microsoft, Yahoo and Google were unrelated to the BetOnSports case, authorities said.
The U.S. Attorney's office in St. Louis has previously prosecuted and settled with other companies over Web-based gambling and gambling ads - agreements that generated more than $40 million in forfeitures and back taxes.
"I do think the prosecution from this office has had a chilling affect on online gambling," Hanaway said.

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