Inside Tiger Woods’ Wild Love Life: From £150K ‘Cash Gift’ to Porn Star Romps After Shocking Split

Tiger Woods, once hailed as the planet’s greatest golfer with 82 PGA Tour wins, has long been a polarizing figure, not just for his unparalleled talent but for the tumultuous details of his personal life that have captivated headlines for decades. Following his highly publicized 2010 divorce from Swedish model Elin Nordegren, the fallout from Woods’ admitted infidelity revealed a staggering web of affairs involving dozens of lovers, from cocktail waitresses to adult film stars. Now, in 2025, fresh revelations about his romantic escapades—including a £150,000 “cash gift” to a porn star and his new relationship with Vanessa Trump, ex-wife of Donald Trump Jr.—have reignited fascination with the golf legend’s wild love life, painting a picture of a man whose private struggles with sex addiction have often overshadowed his sporting legacy.

The unraveling of Woods’ marriage to Nordegren, whom he met in 2001 and married in 2004, remains one of the most infamous scandals in sports history. The couple, who share two children, appeared to have a fairytale life until Thanksgiving 2009, when Nordegren discovered incriminating texts on Woods’ phone while he slept. Among them was a message to VIP event organizer Rachel Uchitel, where Woods allegedly wrote, “You are the only one I’ve ever loved,” just four months after the birth of his son with Nordegren. The ensuing confrontation was explosive: Nordegren reportedly chased Woods with one of his prized golf clubs, smashing the rear window of his car as he fled their mansion. Woods crashed into a fire hydrant and a tree, an incident later attributed to his use of sleeping pills. In the aftermath, scores of women came forward, claiming affairs with the golfer, exposing a pattern of infidelity that Woods himself later admitted, saying, “I was unfaithful. I had affairs. I cheated. What I did was not acceptable, and I am the only person to blame.”

Among the most notable of Woods’ alleged mistresses were adult film stars Joslyn James, Holly Sampson, and Devon James, who reportedly starred in an X-rated film together. Sampson claimed she slept with Woods at his stag do, describing the encounter as a “very sensual, beautiful experience” in an interview with The Sun, adding, “I wanted to give him a birthday to remember… I don’t think he stopped smiling the entire time.” She later stated she wasn’t ashamed of having “f***ed Tiger Woods,” recounting a 40-minute romp after being hired as a lap dancer alongside two other women. Joslyn James, dubbed Woods’ “full-time” mistress by Deadspin, allegedly received a £150,000 “cash gift” from the golfer, according to sources close to Hollywood madam Michelle Braun. James’ relationship with Woods was so well-known that a beauty pageant was reportedly set up for his mistresses, a testament to the scale of his infidelity.

Other women linked to Woods included cocktail waitress Jaimee Grubbs, who claimed to have slept with him 10 times and released voicemails and texts to prove their relationship, and Mindy Lawton, a $7-per-hour waitress who alleged “rough” romps with Woods at his mansion and in the back of his Cadillac in a church car park. Lawton told the News of the World, “All he wanted me for was sex,” and came forward “for his wife to know what a cheat he has been.” Playboy pinup Loredana Ferriolo allegedly received £11,500 per encounter and £46,000 for group sex, per Braun, though Ferriolo denied intimacy, claiming Woods gifted her money and jewelry. New York socialist Cori Rist reportedly joined Woods at expensive hotels during golf tours, while Julie Postle, who nicknamed him “Mr Brightside” in her phone, was allegedly “stolen” from bartender Brian Kimbrough in 2004, per the New York Post.

Woods’ affairs weren’t limited to a single type—others included “sex-hungry cougar” Theresa Rogers, a “really sexy and very well-known” unnamed British TV personality, and multiple cocktail waitresses. The golfer’s cheating ways became so notorious that they overshadowed his 15 major championships, leading to public admissions of sex addiction and a stint in rehab in 2010. Now, in 2025, Woods has announced a new chapter, revealing his relationship with Vanessa Trump via social media with the caption, “Love is in the air.” Vanessa, who divorced Donald Trump Jr. in 2018 after 12 years of marriage, shares five children with the former president’s son. The pairing has sparked intrigue, with fans on X debating whether Woods can finally find stability after years of scandal.

As Woods, now 49, continues his comeback on the PGA Tour, his personal life remains a lightning rod. The contrast between his on-course brilliance and off-course chaos has defined his legacy, leaving fans to wonder if this new romance signals a turning point—or just another chapter in a saga of excess and redemption.