Having Lost $500K Gambling, Dana White Once Spent $30K to Save His Close Friend From Losing Money in the Same Way

UFC President Dana White is a busy man. But that doesn’t mean that he won’t make time for his hobbies and interests. Pick Dana White’s brain, and he’d be able to reel off several eye-watering gambling anecdotes. However, with a net worth of $500 million, the old adage ‘you win some, you lose some’ doesn’t quite apply to White in the same way.

UFC fight nights often take place in the gambling capital of the world, Las Vegas. And as far as White is concerned, it would be remiss not to hit the blackjack tables in Sin City when the opportunity presents itself.

The UFC boss has been known to spend several hours sitting at blackjack tables, leading to notable Las Vegas casinos such as The Palm, The Mirage, and The Wynn attempting to refuse him entry.

White previously won as much as $7 million in one night, but that doesn’t mean that he isn’t immune to the risks of big gambles either.

In 2023, Stephen Deleonardis, AKA SteveWillDoIt of the Nelk Boys, revealed that White was once down an incredible $520,000 during a night of gambling. However, as it happens, White isn’t one to wave the white flag when the chips are down.

“When you play with Dana,” said Deleonardis. “He just won’t let you lose,” the YouTuber added.

On this occasion, SteveWillDoIt managed to amass an impressive $50,000. Sadly, his luck began to fluctuate, eventually losing all of his early winnings. Not one to shy away from a challenge, White stepped up to the plate for the controversial YouTuber.

“Dana buys in, plays, plays, plays, goes up – hands me $30k,” laughs Deleonardis. “Just slides it over, then says, ‘Alright, make a comeback.'”

Deleonardis suffered the same fate the following night, except this time he made good on White’s second intervention, finishing the evening with a cool $40,000 in his pocket.

White’s ability to ride out the losses clearly comes from experience or a genuine belief that bad luck can only last so long. SteveWillDoIt is known for his wild antics.

But as the clip reveals, even Deleonardis was impressed by White’s staying power as the heavy losses began to stack up.

Still, stories such as these have made White a polarizing figure. While his gambling antics have made for some incredible tales, some view his attitude toward his wealth as unhealthy and thoughtless.

Rogan recalls White losing $120K in five minutes

Having previously referred to the boss as a “degenerate gambler“, Rogan has time and again claimed that White’s risky gambling habits give him a lot of anxiety. And apparently, UFC’s Chief Business Officer, Hunter Campbell, also shares these sentiments.

On an episode of the Joe Rogan Experience, the UFC commentator has recalled one such instance and said, “When we got there [to the casino], he (Dana White) was down $600,000″.

“And I was like, What is happening here? I was getting anxious just sitting there watching. Then Taylor Lewan came over. And Dana and Taylor have this deal where Dana teaches Taylor what to gamble. And how to do it… They’re down $120,000 in, what, five minutes?” Rogan added, still shocked at what had just transpired.

However, it seems White enjoys it enough not to particularly care what his friends and peers think of the habit.