John Daly's Wild Love Life: Four Expensive Divorces, Current Fiancee Anna, A 5th Marriage On Cards?

John Daly has impressed golf fanatics and cinephiles alike with his recent cameo as Adam Sandler’s elder brother in the highly anticipated film, Happy Gilmore 2. Through his decades-long career in golf, Daly has carved a legacy that’s as brilliant as it is baffling. In addition to his record-setting drives and major championship wins, his lavish and chaotic personal life has also garnered considerable attention from his fans, particularly his turbulent romantic history.

The golf icon’s love life has been nothing short of a rollercoaster: from four marriages that ended in costly divorces to his long-term relationship with fiancée Anna Cladakis. Once among the highest-paid golfers, John Daly reportedly earned tens of millions during his prime. However, his current net worth tells a more turbulent tale, shaped by expensive divorce settlements, alimony payments, and a long-standing gambling addiction that led to significant financial losses.

From his four marriages to what could end in a fifth marriage, take a look at the women behind the golf legend, John Daly, and the rocky road that brought him to his current partner, Anna Cladakis.

John Daly’s first marriage to Dale Crafton (1987–1990)

Back in the 1980s, Dale Crafton won John Daly’s heart, and the two got married in 1987. Crafton hailed from a wealthy background in Arkansas and worked as a hand model. The couple reportedly struggled from the beginning of their marriage; Daly wanted to move for his golfing career, while Crafton was set on staying in Blytheville. They were a mismatched couple who frequently clashed in opinions, ambitions, and environment. After only three years of marriage, Daly and Crafton parted ways via divorce.

John Daly’s whirlwind romance and marriage to his second wife, Bettye Fulford (1992–1995)

Not long after his divorce from Dale Crafton, John’s paths crossed with Bettye Fulford, a hotel planner from Georgia. Their relationship had also been rocky from the start, and it was a whirlwind romance, to say the least. Fulford had later revealed that she was ten years older than Daly, divorced, and had a teenage son. Still, the couple got married and had a daughter, Shynah.

In 1992, after a violent altercation, John Daly and his then-wife, Bettye Fulford, had a violent altercation during a Christmas party at their Castle Pines home. The golfer, allegedly intoxicated, damaged property and physically assaulted Fulford, leading to his arrest for third-degree assault. He was suspended from the PGA tour and was sent to a 30-day rehab program. This incident marked the breaking point of their marriage, and they divorced shortly after, in 1995.

Daly’s third marriage to Paulette Dean (1995-1999)

In the same year his divorce from Fulford was finalised, Daly met 20-year-old model Paulette Dean, and the two got married later that year. Shortly after their marriage, Dean got pregnant with Daly’s second daughter, Sierra Lynn. After two turbulent (and expensive) divorces and the rehab program, Daly stayed sober for a while. However, eventually, struggles with his golfing career took a toll on the marriage, and after four years, he and Paulette Dean parted ways in 1999.

Daly’s fourth marriage to Sherrie Miller ended in a messy and highly publicised divorce (2001–2007)

Other controversies aside, Daly’s marriage to Sherrie Miller was perhaps his most infamous relationship. Daly and Miller married in 2001 and had a son, Patrick Daly II, in 2003. Despite a promising start, their marriage soon started to fall apart, tainted by highly publicised matters like public fights, gambling scandals, and Miller’s alleged involvement in an illegal gambling ring.

Daly and Miller’s high-profile divorce in 2007 was a messy one, and it turned even more bitter when the golf legend was awarded full custody of their son in 2010 after Miller served jail time. She later sued Daly’s current fiancée, Anna Cladakis, for allegedly ‘wrecking’ their marriage. Their lawsuit is still underway.

John Daly’s rock and long-time fiancée, Anna Cladakis

After his tumultuous marriages, all of which ended in expensive divorces and took up most of his fortune, John Daly met the love of his life, Anna Cladakis, a former Hooters promotional director. Now an entrepreneur, Anna came into John’s life in 2007 and has been by his side ever since. They got engaged in 2014 but have yet to tie the knot.

Today, Anna Cladakis is more than just John Daly’s romantic partner—she plays an active role in his life and career. Whether acting as his caddie, business advisor, or emotional support, she’s been by his side through every high and low over the past 17 years. In April 2025, Daly shared a heartfelt message after their charity golf tournament, thanking Cladakis for her dedication and support. He wrote:

“To my amazing fiancée, thank you for your unwavering hard work & generous heart that made our charity event this week such a HUGE success!”

Is a fifth marriage on the cards?

At 59, John Daly appears content with his life alongside Anna Cladakis. Although the couple has been engaged for several years, they haven’t confirmed any plans to marry in the near future. Still, Anna has expressed in several interviews that, in her heart, she already considers herself his wife.

Only time will tell if Daly walks down the aisle for a fifth time. What do you think about the golf star’s turbulent married life over the years?

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