John Daly Stars In Adam Sandler's Happy Gilmore 2, His Expensive Divorces Burnt His Huge Net Worth

Golf legend John Daly has retained his superstar status ever since his entry in 1990 as a rookie on the Professional Golfers’ Association (PGA) Tour, where he left everyone stunned by winning the PGA Championship. And now, golf’s ultimate wild card is trading his clubs for an acting stint. The Hooters-sponsored fan-favourite golf icon is making waves with his surprise cameo in Adam Sandler’s long-awaited sequel to the 1996 cult classic, Happy Gilmore 2. His role as Gilmore’s older brother in the film has been appreciated by fans and critics alike. 

While Daly’s screen time has fans buzzing, his personal life is drawing equal attention, particularly given his shocking net worth even after such an acclaimed status. You will be surprised to know that the pro golf player, who used to earn tens of millions of dollars in his prime, is left with merely 2 million US dollars at present.

But what has caused a golf legend like Daly to be left with such a shocking net worth after such a glittering career? Well, the reason lies in a strained mix of years of high-stakes gambling, four marriages that ended in expensive divorces, and the player’s lavish lifestyle that burnt through his massive earnings over the years.

John Daly’s journey from a PGA legend to a Netflix star

The Netflix original film, Happy Gilmore 2, premiered on July 25, 2025, starring Adam Sandler in the titular role and John Daly in a key supporting role as his elder brother. Daly’s character is tasked with helping a grieving and washed-up ‘Happy’ find his footing once again. Fans are appreciating the PGA icon’s effortless performance in the movie, delightfully surprised at his cameo. Speaking about his work on the Like a Farmer podcast, Daly said:

"I'm kind of Happy's brother… I had a blast. And Adam's been a friend of mine for a long time. We just had a blast doing it… It was really cool… My agent called me and says, 'Hey, I think you're going to be in Happy Gilmore 2.' I go, 'Really?' And most of the time, it'd be like, ‘Am I going to be on the range? Maybe 10 seconds?’ He goes, 'No, you're going to be his brother. You're going to get him back to playing golf.'"

John Daly’s meteoric rise and fall after a USD 50M+ gamble

Those familiar with John Daly’s work are well aware of his larger-than-life status in golf. As one of the highest-paid players, Daly was once projected to build a fortune that could rival golf’s elite. However, he lost a massive chunk of his fortune to a series of casino failures. The PGA icon has admitted that he lost around 50 to 57 million in gambling between 1991 and 2007. 

In 2005, Daly had an infamous post-match moment when, after losing to Tiger Woods, he blew a staggering USD 1.65 million within just five hours at a Vegas casino. In the later years, he toned things down and limited himself to only USD 25 slots, but his gambling addiction, on top of his high-maintenance lifestyle, drastically impacted his finances.

Inside John Daly’s turbulent (and expensive) marriages that ended with millions in settlements

If we keep his casino losses aside, Daly’s personal life has been no less chaotic. The golf icon has been married not once, but four times, each ending in expensive and high-profile divorces. According to legal documents and media reports, Daly has spent millions on all four of his divorce settlements and alimony. 

After his four failed marriages, Daly is now in a relationship with his long-time girlfriend of over 17 years, Anna Cladakis. The couple has been engaged since 2014 and is still going strong. However, they have yet to tie the knot, and it’s a matter of waiting to see if marriage number five is on the cards. 

The reality behind John Daly’s current net worth

John Daly has earned around 12 million US dollars from golf tournaments in the prime of his career, with endorsements from biggies like Loudmouth Golf and Rock Bottom Golf. Despite such high earnings, the player is left today with just around 2 million US dollars. For one of the most recognisable figures of golf, who once commanded tens of millions for a single match, the current number seems shockingly low.

Despite his tumultuous personal life that consumed most of his life’s earnings, the 59-year-old golf veteran remains a key figure on the PGA Tour Champions circuit as well as in pop culture. Known for his unapologetic persona, Daly is a fan favourite for his natural humour and raw talent, whether he’s playing golf with a cigarette in hand or promoting his latest merchandise line.

And now, with his acting stint in Happy Gilmore 2, John Daly remains worthy of the spotlight even after all these years.

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