Charlie Sheen Wins $1 Boxing Bet He Placed Because Of A Dream

Pacquiao vs De La Hoya BetBack in 2008, Charlie Sheen was at the height of his success. He was 4 years into the hit US show ‘Two and a Half Men’ after a career of other successes such as Platoon, Wall Street, Hot Shots!, and the Scary Movie films.

He was also well on his way to absolutely losing his mind through drug and alcohol abuse though, so if he had offered you a betting tip, you would have done well to nod and smile and then completely ignore him.

Sheen was a big gambler at the time, and there was one bet in particular that he was very right about, and the crazy thing is, he said the bet came to him in a dream.

It was Manny Pacquiao vs Oscar De La Hoya.

A week before the fight, he dreamt that Pacquiao “was going to beat De La Hoya like a drum“, so he stuck $1 million on the result, and at this time, the Pacman was not the favourite to win. De La Hoya, known as Golden Boy, was more fancied, so the odds were around 3/2 for Pacquiao when Sheen placed the bet.

But Oscar De La Hoya was 6 years old than Manny Pacquiao, and although he had enjoyed an excellent career, De La Hoya was in something of a ‘win one lose one’ streak, whereas Pacquiao was in his prime and hadn’t lost a fight in 2 years.

In the end, PacMan was just too quick, landing numerous jabs before Oscar even knew what was happening, and evading most of his attempts at retaliation. De La Hoya was reduced to focussing on body shots, but as the rounds went on, Pacquiao’s combinations were landing harder and more frequently, and in round 8, De La Hoya’s team threw in the towel.

He retired shortly afterwards.

Sheen Felt Nothing

Charlie Sheen $1 Million Bet

Credit: Justaufo / Flickr

It was the perfect result for Charlie Sheen, and not just because he won.

Assuming he got odds of around 3/2, Sheen’s $1 million would return $2.5 million, with $1.5 million of that being winnings. It was the biggest bet Sheen had ever placed, and his biggest return too, but according to him, he felt no joy.

He spoke about the bet in an interview with the New York Times in 2012, saying of the win:

“It was like, pfffft, whatever. I felt nothing.”

So why was it the perfect result?

Because once he won such a huge sum of money and felt no excitement from it, he realised that he was done with gambling forever. It no longer held any meaning for him.

In the same interview I previously mentioned, he explained:

“I went, okay, there’s nothing left for me here. Unless my children are involved in the wager, no sense in making it, you know?”

I realise that his explanation isn’t exactly clear, but remember, this was during his peak “winning” period, while he was still talking about having tiger blood and Adonis DNA.

These days Charlie Sheen says he is a retired gambler rather than a recovering gambler, noting the difference. It’s not that he doesn’t gamble because he can’t control it, he doesn’t gamble because he doesn’t see the point anymore.