Kimberly Guilfoyle, the U.S. ambassador to Greece and Donald Trump Jr.’s ex-fiancée, allegedly conspired with her successor’s jilted billionaire ex in an effort to derail the romance that led to Don Jr.’s May 21, 2026, wedding, according to claims published June 11, 2026.
The 57-year-old former Fox News host and prosecutor is accused of working alongside William “Beau” Wrigley, 62, heir to the Wrigley chewing gum fortune, to spread damaging rumors about Palm Beach socialite Bettina Anderson throughout elite social circles. Anderson, 39, went on to marry the 48-year-old Don Jr. despite the alleged campaign.
Wrigley had previously been engaged to Anderson before she began dating Don Jr., whose public hand-holding photos with Anderson prompted Guilfoyle to reach out to the billionaire, sources said.
The Public Face vs. the Private Sting
While Guilfoyle offered gracious public comments about the relationship, telling an interviewer in a piece published January 5, 2026, “I’m happy for Don. I wish him, of course, all the best,” sources described a very different reality behind closed doors.
The former couple, who still reportedly co-own a Florida home, had not fully separated their belongings, with Don Jr.’s clothes and shoes still at Guilfoyle’s residence, sources told People magazine. One source said Guilfoyle was humiliated by the public breakup and “is determined not to be seen as a loser.”
An Alleged Alliance Born in Palm Beach
“When they found out that Don and Bettina were dating, Kimberly and Beau teamed up to break them up,” one source said. “It was the most unholy of alliances, let’s just put it that way.”
The strategy allegedly involved painting Anderson as a social climber pursuing Don Jr. for his wealth, celebrity status, and connection to the Trump family name. Sources claim Guilfoyle and Wrigley leveraged their Palm Beach connections to generate negative press coverage depicting Anderson as calculating and opportunistic.
According to sources cited in the report, the two met to plan their approach, and weeks later were seen dancing together at a Palm Beach hotel fundraiser that Wrigley was co-chairing. “Kim got in contact with all of us,” one Palm Beach socialite who had known Anderson since childhood told reporters.
Awkward Optics on the Dance Floor
The fundraiser generated gossip for multiple reasons. Wrigley had separated from his third wife, author Sue Hostetler, days before the event. Hostetler, who began dating Wrigley shortly after his split from Anderson and was a co-chair of the fundraiser, did not attend. Guests watched as Wrigley and Guilfoyle danced together, with one eyewitness describing them as “bumping and grinding.”
A source close to Guilfoyle offered a different version, saying Wrigley initiated contact and shared concerns from his previous relationship with Anderson that he believed Don Jr. should be aware of. A source close to Anderson responded bluntly: “All this story really shows is just how jealous and petty Guilfoyle really is.”
A Wedding That Stole the Spotlight
The alleged plot failed to stop the wedding. Don Jr. and Anderson married in a private West Palm Beach ceremony on May 21, 2026, then celebrated over Memorial Day Weekend with a destination wedding on the private Bahamian island of Little Pipe Cay.
Ivanka Trump, Eric Trump, and Tiffany Trump attended, though President Donald Trump, First Lady Melania Trump, and Barron Trump were notably absent. Don Jr.’s five children from his previous marriage to Vanessa Haydon — who has since been romantically linked to golfer Tiger Woods — attended the festivities.
Don Jr. announced his engagement to Anderson at the White House Christmas party in December 2025, just over a year after ending his six-year relationship with Guilfoyle, which included a four-year engagement that began in 2020. Anderson is the daughter of Harry Loy Anderson Jr., who became the youngest bank president in the United States at age 26.
Guilfoyle has been making headlines in Greece with late-night appearances at high-profile events and nightclubs that she describes as part of her relationship-building approach. She has also weighed in on her first ex-husband, Gavin Newsom, whom she says is “one thousand percent” planning a 2028 presidential run. Guilfoyle and Newsom married in 2001 and split in 2006. She was also married to Eric Villency; they divorced in 2009.
According to explosive new claims, the Trump family’s most-watched love triangle has reached its next chapter, with the newlyweds appearing unbothered by the swirling allegations.
