Does David Letterman Have a “Poker Problem?”



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Demonstrating the validity of the information that appears in its pages, a noted tabloid rag has recently surmised that former “Late Night” host David Letterman is “obsessed” with poker – to the point where he is risking all that he has built in the entertainment industry.

The National Enquirer recently ran a story that, while entirely plausible, didn’t seem to have much in the way of evidence. Breathlessly stating that Letterman, who retired from his critically acclaimed and popular late night show in 2015, is looking at “upping the ante” (their words, not this writer’s) by delving into “high stakes” poker. According to the Enquirer, Letterman has been teaching his son how to play the game and this is “driving him” to take “his skills to Las Vegas, where he dreams of winning big!”

Of course, all this breathless concern is based on a singular source that isn’t named. The source taps the name of a couple of the biggest poker “names” in the entertainment world – Ben Affleck and Tobey Maguire – with the source hand-wringing to the fish wrap, “Those guys are as close to professional players as you can get. Dave’s totally out of his league with them…he might be worth $400 million, but those guys will have no hesitation in cleaning him out!”

Now, never let it be that the evidence there to back up these assumptions. Affleck has been having issues with his marriage to actress Jennifer Garner that have been taking up most of his time – not poker – and Maguire is notoriously quiet about his personal life, although his past poker journeys at the World Series of Poker and in high stakes cash games around Hollywood have previously been noted. The Enquirer continues to piece together flimsy evidence that, because Letterman’s idol Johnny Carson was an avid poker player, that Letterman himself now wants to follow that path and that his friends are concerned he will “end up flat broke like NYPD Blue creator David Milch.”

Milch’s story is actually documented well. Milch, who also created two popular HBO series Luck (canceled after one season due to deaths of horses involved with the show) and Deadwood, gambled away approximately $25 million between 2000 and 2011, per the Hollywood Reporter. The Reporter details the extent of the financial troubles of Milch, who didn’t lose the money at poker (he was, however, a regular of the Carson poker games) but through horse racing. His ownership of thoroughbreds – and his wagering on the races in the popular California horse racing facilities – have allegedly seen Milch blast through upwards of $100 million and that he owes the Internal Revenue Service around $17 million.

Strangely enough, none of this purported “poker fever” was found in an actual interview with Letterman released this month. New York Magazine’s entertainment website Vulture recently sat down with the soon to be 70-year old and found someone quite as ease in his retirement. He does regret not being able to call out certain politicians – especially one in particular that he skewered for years – but applauds those such as Stephen Colbert, Seth Meyers, and the cast of Saturday Night Live for carrying the mantle. Nowhere in the Vulture article is there any inkling that Letterman has become a raging gambling addict looking to put his fortune on the turn of a friendly card.

Whether Letterman is getting ready to attack the Super High Roller Bowl this year (hey, Poker Central and ARIA? There’s someone to call!) or is just going to sit back and enjoy the fruits of his lifetime of labor, the breathless vagaries of the Enquirer – which use to be laughed off as the insipid jokes that they were – seem to be completely out of line. And if they’re true? Who wouldn’t want to see David Letterman at their poker table?

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