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Rupert Murdoch, Down $530M in Antitrust Fight, Now Faces a Poker Champ Who Trained With Bill Gates

Rupert Murdoch's News Corp. (NWS) has already lost $530 million in a high-stakes wager on the supermarket advertising industry, and now it faces another round of betting, this time in an antitrust suit filed by tiny Insignia Systems (ISIG).

As Murdoch and his lieutenants at the News grocery coupon unit, News America Marketing Group, decide whether to raise or fold in Insignia's antitrust suit against them, they probably ought to know that they're dealing with an actual poker player: Insignia CEO Scott Drill (pictured) is a ranked poker player who has won more than $100,000 in various tournaments since 2005, and who honed his game in all-night sessions against Bill Gates -- yes, Bill Gates of Microsoft (MSFT) -- when the pair attended Harvard together.

In the suit, Insignia claims News America has maintained a virtual monopoly on supermarket coupon advertising through predatory pricing, exclusive contracts and by spreading false information about Insignia. News denies the claims, but it has lost two previous rounds in this litigation: Rival companies Valassis (VCI) and Floorgraphics have both forced settlements out of News -- to the tune of $500 million and $29.5 million, respectively -- in suits similar to Insignia's. A trial date has been set for May 1 April 12, so the clock is ticking and Murdoch must decide whether to bow out or throw more chips into the pot.

Drill began his poker career playing against Gates at Harvard in the 1970s. Drill would play against Gates three or four times a week, sometimes 24 hours straight, he told this web site. Drill described Gates at the time as, "Nice guy. Computer geek. Poor hygiene":

Q: Did you have any nicknames for him?

A: Gravy Train Gates.

Q: Did you hang out with him or just play poker?

A: Just poker.

Q: Was he a good poker player?

A: Only fair.

Drill most recently placed 12th in the 2008 Minnesota State Poker Championships, winning $2,712. His biggest take was $62,740 in the 2006 Heartland Poker Tour, which he won.

As for the much bigger stakes at the News table, Drill appears to hold better cards than Murdoch. He's the beneficiary of all the discovery revealed in the Valassis and FGI cases, and he knows that News has thus far been unable to withstand a trial or convince a jury that its tactics are legal. A source tells BNET that Drill has a number in mind, and that number is a lot more than FGI won.