Kimberly Guilfoyle and billionaire ex allegedly conspired to undermine Don Jr.'s new relationship
Two scorned exes, one a former Fox News personality turned U.S. ambassador, the other a billionaire chewing gum heir, allegedly joined forces last December to sabotage Donald Trump Jr.'s relationship with the woman who is now his wife. That is the central claim in a Daily Mail report built on anonymous sources close to both former couples, painting a picture of jealousy, social warfare, and Palm Beach pettiness aimed squarely at Don Jr. and Bettina Anderson.
The claims are sourced to unnamed insiders, and none of the four principals, Guilfoyle, William "Beau" Wrigley, Don Jr., or Anderson, are quoted responding. The Daily Mail says it reached out to all four for comment. What the reporting does offer is a detailed, if anonymously sourced, account of how two people who lost their respective partners to each other allegedly tried to poison the new couple's happiness through negative media coverage and whisper campaigns across Palm Beach society.
The alleged alliance between Guilfoyle and Wrigley
Sources told the Daily Mail that Guilfoyle and Wrigley met in December 2024 to discuss tactics after learning Don Jr. and Anderson were dating. One source close to the situation described it bluntly:
"When they found out that Don and Bettina were dating, Kimberly and Beau teamed up to break them up. It was the most unholy of alliances, let's just put it that way."
The alleged plan, sources claimed, centered on spreading the narrative that Anderson was a social climber and facilitating negative media coverage, mostly targeting Anderson rather than Don Jr. A Palm Beach socialite who told the Daily Mail she has known Anderson since childhood said Guilfoyle contacted members of their social circle directly: "Kim got in contact with all of us."
There is a dispute even among the anonymous sources about who initiated the contact. One source claimed Guilfoyle reached out to Wrigley. A source described as close to Guilfoyle insisted it was Wrigley who reached out first.
By February 2025, the two were seen together publicly. The Daily Mail reported Guilfoyle and Wrigley attended a fundraiser at the Breakers in Palm Beach, where Wrigley served as co-chair. An eyewitness described the pair as "bumping and grinding" on the dance floor, a display that raised eyebrows given the context.
How the relationships unraveled, and intersected
The backstory connecting all four people stretches back years and winds through some of South Florida's most expensive real estate.
Anderson, now 39, was previously engaged to Wrigley, the 62-year-old heir whose fortune Forbes pegs at $3.6 billion. Sources told the Daily Mail their relationship moved quickly. A former Wrigley staffer described the dynamic: "Beau had just gotten divorced and Bettina was this young, hot girl in the area." That same staffer added, "I think she was genuinely into him and the relationship, and he wasn't."
The couple planned an elaborate destination wedding in Ireland, described by one source as "a five-night affair" with "specific different dress colors and dress lengths and themes each night." But sources claimed Wrigley demanded Anderson sign a prenuptial agreement weeks before the ceremony, and when she refused, he pulled the plug.
The manner of the cancellation, if the sources are accurate, was striking. A guest told the Daily Mail that Wrigley "wrote an email in the middle of the night to everybody invited to the wedding saying the wedding is off." Insiders claimed he then removed Anderson from his $98 million North Palm Beach estate and dispatched a staff member to retrieve her engagement ring.
A former staffer summed it up: "She was heartbroken." Another source called the breakup "cruel and awful."
Within months, the Daily Mail reported, Wrigley began dating Sue Hostetler. They married in 2021. That marriage, too, ended, Wrigley and Hostetler divorced in early 2025, just days before his appearance alongside Guilfoyle at the Breakers fundraiser. Hostetler, who had served as co-chair of the annual Everglades Foundation gala, was a no-show at the event.
Don Jr. and Anderson's path to marriage
The Daily Mail reported it first published photographs of Don Jr., 48, and Anderson together on August 17, 2024, showing them at brunch in Palm Beach. In December 2024, the outlet reported it revealed the two were officially a couple after photographing them walking hand in hand after a dinner celebrating Anderson's 38th birthday.
The couple's relationship progressed despite whatever interference the alleged Guilfoyle-Wrigley campaign may have generated. Wedding plans were reportedly put on hold at one point, but Don Jr. and Anderson got engaged in April and married in a private ceremony in West Palm Beach.
They later hosted a ceremony on Little Pipe Cay in the Bahamas. The Daily Mail reported they announced their engagement at the White House holiday party in December 2025, posing alongside Dr. Oz and his wife Lisa.
Anderson did sign a prenuptial agreement this time around, the Daily Mail noted, a detail that contrasts with the dispute that ended her engagement to Wrigley years earlier.
Guilfoyle's position and the jealousy claims
Guilfoyle, 57, was Don Jr.'s fiancée before the split. The Daily Mail reported she appeared alongside him at a campaign event in Kentucky just weeks after the first photographs of Don Jr. and Anderson surfaced in August 2024. She still co-owns a $17.5 million home in Jupiter, Florida, with Don Jr.
President Trump dispatched Guilfoyle to serve as U.S. Ambassador to Greece, a posting that placed an ocean between her and the Palm Beach social scene where much of this drama unfolded. Don Jr. and Anderson have continued to be seen together in Jupiter and across South Florida.
The anonymous sources offered sharp assessments of Guilfoyle's alleged motivations. One source close to the former couples told the Daily Mail:
"Kimberley is determined not to be seen as a loser. She is wild with jealousy about Bettina and has since made every effort to make sure she is seen with wealthy men, very heavy hitters."
An insider described as close to Anderson was more direct: "All this story really shows is just how jealous and petty Guilfoyle really is."
A source close to Guilfoyle pushed back on the entire narrative, telling the Daily Mail: "She remains focused on serving her country and fulfilling a lifelong dream to work in administration where she is making a difference for the world."
What remains unverified
Readers should weigh this reporting with clear eyes. Every substantive allegation rests on unnamed sources. No documents, messages, or on-the-record statements support the core claim of a coordinated effort to break up Don Jr. and Anderson. The Daily Mail reported reaching out to all four principals; whether any responded is not stated.
The specific "tactics" Guilfoyle and Wrigley allegedly discussed remain undefined. The negative media coverage they supposedly helped facilitate is not identified by name or outlet. The location of their alleged December 2024 meeting is not reported. These are significant gaps in a story that asks readers to accept a serious accusation, a deliberate conspiracy to destroy a family relationship, on the word of people who will not attach their names to the claims.
The broader Trump family orbit has drawn intense media scrutiny throughout the current administration, from personal milestones among White House staff to the health struggles of longtime allies like Rudy Giuliani. The appetite for palace intrigue is bottomless. That does not make every anonymous claim true.
The real takeaway
If the sources are telling the truth, what emerges is not a political scandal but a personal one, two people allegedly so consumed by resentment that they tried to wreck a relationship rather than move on with their own lives. Don Jr. and Anderson appear to have moved on just fine. They married. They celebrated at the White House. They are building a life together.
Guilfoyle holds a diplomatic post representing the United States abroad. Wrigley sits atop a $3.6 billion fortune. Both had every resource and reason to turn the page. If they instead chose to wage a petty campaign against their exes' happiness, that says far more about them than about the couple they allegedly targeted.
The best revenge, as the saying goes, is living well. Don Jr. and Anderson seem to have gotten the memo. Whether their exes did is another question entirely.






