Did Dan Bilzerian Make His Millions Playing Poker?

"Did I really make all my money playing poker? Who fucking cares?"

I rarely claim 100% knowledge on the affairs of people I don't know personally, but I can say with 99% certainty that the answer is "not a chance". Please note that the following text isn't, nor is meant to be, quoted verbatim, yet read on to see why the details aren't important.

Dan tipped his hand when he said in an interview with Howard Stern that he won $50 million playing poker in a single year, with the implication that he must have made far more than that by getting his start as a poker pro. He then thumbed his nose at other high stakes overachievers by saying, "really, who else has done that?"

So how am I so certain that he actually didn't get his start as a poker pro? I've been involved in online poker for 12 years and more or less know of all the biggest names in the game. From what I've read, I'm not the only one who never heard of Dan Bilzerian until a few years ago when he made a deep run in the WSOP $10,00 Main Event, and that's because other than this rather "meh" non piece of news, he never made any significant mark on the poker world. No big tournament wins, no WSOP bracelets, etc.

Ok...no big deal. All serious players know that besides a handful of outliers, all of the biggest winners in poker play cash games, not tournaments. Online players also know basically every single player who plays in the biggest stakes in the world, which one would have to play in order to make anywhere near $10 million, let alone $50 million. 

I say "basically" because there were some players who tried to be anonymous in order to get action, but since players who regularly play in games where millions of dollars are won or lost in a session draw a lot of attention to themselves, the desired anonymity never lasts and their identities are eventually outed. Dan's name was never among these players, and someone boasting of making so much money is completely contrary to the idea of being anonymous.

So we have established that he has no public record of winning a significant sum of money. However, that doesn't rule out one last possibility: that he made a boatload of cash playing in private, ultra high stakes home games populated with celebrities and other wealthy people with money to burn.

I have read that he has played in games with Toby Maguire, and even was able publicly to vouch for Major League baseball star, Alex Rodriguez, that he was not present at this home game on a specific date, implying that Dan was, in fact, a regular at this home game, and thus a reliable witness. Admittedly, since I don't have any real interest in this subject (a total contradiction after writing this much, I know :), I haven't even bothered to verify whether this particular tidbit is true. However, it's not necessary because....

Paid in full, courtesy of Alex Rodriguez

People don't get invited into private, ultra high stakes games, unless they first have a ton of money in the first place!! In other words, the other players in the game aren't going to ignore their itch to gamble for stakes higher than anything available in public casinos just to let Dan grind up his roll in $5/10 games, even if he is funny and brings entertainment...although it's quite likely that these would be reasons why he would be invited back :)

Final note: 

In another interview where Bilzerian continued the outrageous claim of making $50 million playing poker, he followed that up with a peculiar humble brag, saying that his skill level is somewhere between a good high school player to perhaps the minor leagues, yet he is able to win so much because the players he fleeces play at the tee-ball level (again, not a verbatim quote, but close). Again, this doesn't fit the narrative, as anyone publicly insulting the generous benefactors that they have been hustling isn't likely to ever get invited back in those games.

I do, however, find it to be quite likely that he has won millions in these games, but hopefully we can finally shut the door on whether or not this is how he became wealthy in the first place.