Sklansky was born in Teaneck, New Jersey and he attended the University of Pennsylvania before dropping out to pursue work as an actuary. He would go on to become one of poker's most impactful authors.
Not money or power, but influence
An influential author and multimillionaire, Sklansky explained in an interview with Stacked Magazine in 2010 that he's not motivated by money.
"The quest for big money is usually done by people with very expensive tastes – which I don't have – or people who have the desire for power as opposed to influence," Sklansky told the magazine. "I prefer influence. When you have power, people do what you say because they're afraid of you."
"$20M is enough," Sklansky said at the time.
"A lot of people go for a lot of money because they're trying to stave off depression. It's become a game to them because they would be bored if they weren't going after it. They don't want to face the fact that their lives suck."
Influence, to Sklansky, didn't suck. It was everything.
"I just want people to look at me like they did Solomon back in the days of Israel. Whenever people have a problem, I want them to think, 'What would David do here?' I know that plenty of people do that already."
Influence courts controversy
His influence would become the center of a major controversy in the late 2000s when he reportedly had an inappropriate relationship with a young poker player named Brandi Hawbaker.
Hawbaker was a regular on the TwoPlusTwo poker message board forums, of which Sklansky was a co-owner. She would outline the power-based relationship with him in a series of private emails that were shared throughout the poker community in 2007 and 2008.
Hawbaker took her own life in April of 2008. Her previous struggles were well-documented, but the online harassment and association with Sklansky linger as contributing factors. Matt Berkey covered the story in an in-depth episode of Only Friends in 2023. Sklansky returned to the headlines in 2026 with another controversy after his arrest on suspicion of domestic battery in January, but he was released, and no charges were filed.
Sklansky continued to write up until 2023, when his final book, Small Stakes No-Limit Hold'em: Help Them Give You Their Money was published.