The Palm Beach rumor mill is spinning faster than ever, and a juicy new report published June 11, 2026, suggests that Donald Trump Jr.’s ex-fiancée Kimberly Guilfoyle wasn’t quite as gracious about his new marriage as she let on. According to explosive new claims, Guilfoyle, 57, the U.S. ambassador to Greece, allegedly teamed up with the bride’s billionaire ex-fiancé in a behind-the-scenes plot to torpedo Don Jr.’s romance with Palm Beach socialite Bettina Anderson.
The alleged co-conspirator? William “Beau” Wrigley, 62, the heir to the Wrigley chewing gum fortune and Anderson’s former fiancé. Sources say the unlikely duo joined forces after Don Jr., 48, moved on from Guilfoyle to the 39-year-old Anderson — a pairing that left both jilted exes nursing very public wounds.
An Alleged Alliance Born in Palm Beach
According to sources cited in the report, Guilfoyle reached out to Wrigley in December 2024 — right around the time Don Jr. and Anderson were first photographed holding hands in public. The two reportedly met to strategize, and weeks later were spotted dancing together at a fundraiser Wrigley was co-chairing at a Palm Beach hotel.
“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 alleged playbook was straightforward: spread the word around Palm Beach that Anderson was a social climber chasing Don Jr. for wealth, celebrity, and access to the Trump family name. Sources claim the pair leaned on their Palm Beach contacts to help shape negative press coverage portraying Anderson as a calculating operator.
One Palm Beach socialite who said she had known Anderson since childhood told reporters, “Kim got in contact with all of us.”
Awkward Optics on the Dance Floor
The fundraiser appearance raised eyebrows for more than one reason. Days earlier, Wrigley had separated from his third wife, author Sue Hostetler, whom he began dating shortly after his split from Anderson. Hostetler was actually a co-chair of the event but did not attend — leaving guests doing double takes as Wrigley took to the dance floor with Guilfoyle. An eyewitness described the pair as “bumping and grinding.”
Not everyone tells the story the same way. A source close to Guilfoyle pushed back, claiming it was actually Wrigley who reached out first, allegedly sharing concerns from his prior relationship with Anderson that he felt Don Jr. “should be aware of.” A source close to Anderson, meanwhile, was less diplomatic: “All this story really shows is just how jealous and petty Guilfoyle really is.”
The Public Face vs. the Private Sting
Guilfoyle, the former Fox News host and former prosecutor, had previously taken the high road in public. In an interview published January 5, 2026, she addressed Don Jr.’s engagement for the first time, saying simply, “I’m happy for Don. I wish him, of course, all the best.”
Behind the scenes, sources told a different story. Guilfoyle, who reportedly still co-owns a Florida home with Don Jr., was described as humiliated by the public end of their engagement. “Kimberly is determined not to be seen as a loser,” one source said. Another told People magazine that as of late 2025, the former couple hadn’t fully cleared their belongings from each other’s homes — Don Jr.’s clothes and shoes were reportedly still at Guilfoyle’s place.
A Wedding That Stole the Spotlight
Whatever Guilfoyle and Wrigley allegedly set in motion didn’t take. Don Jr. and Anderson tied the knot in a private West Palm Beach ceremony on May 21, 2026, followed by a destination wedding celebration over Memorial Day Weekend on the private Bahamian island of Little Pipe Cay. The lavish affair has drawn comparisons to John F. Kennedy Jr.’s iconic 1996 wedding to Carolyn Bessette.
Ivanka Trump, Eric Trump, and Tiffany Trump were among the guests, 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 — were on hand for the festivities.
The couple’s whirlwind has been quite the journey. Don Jr. announced his engagement to Anderson at the White House Christmas party in December 2025, just over a year after he and Guilfoyle ended their six-year relationship, 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.
As for Guilfoyle, she has been making a splash in Greece, with late-night appearances at high-profile events and nightclubs that she says are part of her relationship-building approach. She has also been making her own headlines back home — including weighing 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, with whom she divorced in 2009.
For now, the newlyweds appear unbothered by the swirling allegations. The honeymoon is on, the photos are out, and the Trump family’s most-watched love triangle has officially reached its next chapter.