So, the interwebz is all abuzz over actor Ashton Kutcher’s admission that he acted as “a front for the largest national sports-betting syndicate in America.” Kutcher made the claim in the latest issue of Esquire, in which he revealed a decent understanding of the intricacies of such a sports betting operation, and how sportsbooks do their best to avoid taking action from these groups. Which is why the aforementioned syndicate “sent [Kutcher] in. I basically just placed the bet.” Kutcher explained the “hypothesis had been that the house would just assume that I was a dumb actor with a lot of money who liked football.” Kutcher claimed the unnamed syndicate made $750k in four weeks betting on college football before the books caught on.

David Purdum, who covers The Linemakers beat on Sportingnews.com, says Kutcher’s story “checks out in Vegas.” A former Vegas sportsbook manager told Purdum the scenario played out in the early part of the last decade, when the Vegas books “thought they had a sucker on the hook, then he won $800k in four weeks. They had to shut him down.”

Purdum suggested Kutcher was obliquely referenced in Michael Konik’s The Smart Money: How The World’s Best Sports Bettors Beat The Bookies Out Of Millions. Konik’s book describes a “shadowy group of gamblers known for their expertise in beating the Vegas line” known as the ‘Brain Trust’ who occasionally used celebrities as fronts to place wagers. This group was led by Rick ‘Big Daddy’ Matthews, a pseudonym many readers have interpreted as a reference to legendary sports betting figure Billy Walters, who was a part of the equally legendary Computer Group in the 1980’s. Konik has declined to comment on such speculation, citing the book’s note about “honoring privacy.”

SHOOTING THE MESSENGER

So, we’ve got a question. If Kutcher claims to have merely acted as “a front” who “basically just placed the bet’ on someone else’s behalf, is that not the very definition of messenger betting, which is illegal in Nevada? Case in point: Robert Walker, a member of Walters’ present-day betting syndicate ACME Group Trading (and director of maintenance at a Walters-run golf course), pleaded guilty last Wednesday to causing a violation of record keeping and procedures. In doing so, Walker avoided felony charges of violating currency transaction reporting laws. The plea deal resulted in a sentence of one year of unsupervised probation, the lightest punishment the judge could have dished out.

Walker’s crime? He placed four wagers totaling $72k at the Golden Nugget sports book between March and April 2011, but never disclosed to the Nugget that he was wagering on behalf of the ACME Group. Federal law requires casinos to file reports on all transactions over $10k, and Walker’s failure to tell the Nugget whose money he was wagering meant the Nugget’s reports weren’t in compliance.

This isn’t Kutcher’s first delicate dance with federal statutes. A couple years back, Kutcher caused a kerfuffle after he guest edited an online edition of Details magazine in which the noted tech investor touted a dozen startups he felt were poised to break big. Trouble was, Kutcher was personally invested in eight of the 12 and had “business entanglements” in two others, all of which he failed to disclose while singing these companies’ praises. If any of those firms had been planning an IPO or privately trading shares on the secondary market, Kutcher’s pimping would have fallen afoul of SEC regulations. Fortunately for Kutcher, the Federal Trade Commission chose to view it as a case of ‘Dude, Where’s My Ethics?’ and let the matter slide.

Will Nevada lawmen and/or the Internal Revenue Service take an equally lenient stance? The trick would be proving that Kutcher was compensated by his unidentified syndicate friends for placing their wagers. And given the estimated date of Kutcher’s front man antics, the statute of limitations has likely run out the clock. Still, having a bunch of cops drag him away from his latest red carpet appearance in handcuffs would make for a thoroughly entertaining episode of Punk’d.