I’m not sure how many of you are fans of the TV show Millionaire Matchmaker. Personally, I’m partial to High Stakes Poker, Spartacus, and Entourage. But I happened to catch Millionaire Matchmaker a little over a year ago when I was traveling with a girlfriend. The show’s format is pretty simple: Its namesake star, Patti Stanger, introduces millionaires to potential wives who possess varying degrees of hotness.  The single episode I watched featured one of the show’s more notorious millionaires, a dude who calls himself Jimmy D.     On the show, he came across as extremely cocky and seemed brasher than would be standard for a millionaire who resorts to TV to meet a girl. He continually referred to himself in the third person, dressed like a pimp, bragged about how great his life is, and griped about women using him for sex… You know the type.   

Well, last summer, during the World Series, I was hanging out in Bobby’s Room with Kido Pham and David Kim. We were waiting to start a $200/$400 pot limit Omaha game. That’s when this guy wandered in, obviously drunk, and introduced himself as Jimmy D.     Poker-players who didn’t know him from the show, might have known him from a 2+2 thread on which people posted about him owing them tons of money. I, of course, had seen this guy on Millionaire Matchmaker, and my girlfriend and I did Jimmy D. impressions for a week after the show aired. So, in a weird way, it was kind of cool – sort of like a goofy sociological experiment – to actually see Jimmy D. up close.    Not one to disappoint, he immediately began talking about the fact that he won $500,000 playing blackjack. Then he went on about having just had sex with two girls in his room. I told him one of my girlfriends was a huge fan. Then I called her up so she could have a chance to chat with the famous Jimmy D. 

After the phone call ended, he finally asked the six-figure question: “Does anybody here want to play heads-up for half-a-million-dollars?” 

I jokingly said to him, “You’re not famous for being a professional poker player, are you?”
 
He said he wasn’t. So it’s nice to know that he’s honest about his card-playing prowess.     Sure that I could sell off as much of my action against him as I wanted to, I offered to take him on.     Removing $200,000 in cranberries from my bag, I said, “Let’s buy in for 200K, just to get started.”    At first he seemed shocked to see the money. Then he had to text his buddy. After that, he said to me, “I sent my friend your picture and he tells me that you’re an online poker genius. I don’t want to play you anymore.”    No problem. Plenty of guys walk into Bobby’s Room, say they want to gamble, and back out before their money hits the felt.  But, after reneging on their offer, most would-be players leave the room. Not Jimmy D. He just sat there on one of the leather chairs, making himself comfortable in Bobby’s Room, watching as our PLO game got underway.

Oblivious to what was going on around him, he kept talking about himself, telling everyone how rich he is. Finally, his stay ended in the only way that something like this could end: One of the players in the game slipped 20-bucks to the floorman and asked him to kick out the loud guy.    He did it tactfully, our game went on, and I got a good story about almost playing heads-up against Jimmy D.