A scathing new report on Donald Trump Jr. has documented his need to “up his girlfriend game,” as he transformed from his father’s “weak-chinned,” nepo baby “failson” into a national power player and leader in the rise of America’s edgelord tech bros and their “neofascist, misogynistic, white-supremacist subculture.”
That meant that Trump Jr. had to say good-bye to Kimberly Guilfoyle, his longtime girlfriend and one-time fiancée, as his father, Donald Trump, “prepared to storm back into the White House,” as New York magazine reported.
In Guilfoyle’s place, Trump Jr. chose Bettina Anderson, a 38-year-old Florida socialite and “actual to the manor born WASP,” according to the report by investigative journalist Nina Burleigh says. Unlike Guilfoyle, born in San Francisco to an Irish immigrant father and a Puerto Rican mother, Anderson comes “from the enclaves of Palm Beach that used to look down on the Trumps,” Burleigh added.
Also, unlike 56-year-old Guilfoyle, Anderson is younger than 47-year-old Trump Jr. and “doesn’t appear to have submitted to the Mar-a-Lago face restructuring popular among many ladies in Palm Beach MAGAland,” Burleigh also wrote.
Palm Beach society is “a little surprised” that Anderson would date Trump Jr., Burleigh reported. An insider told her that he “is the most despised member of the family. … an (expletive), a spoiled heir.”
To that assessment of Trump Jr., Anderson fired back on Instagram Story over the weekend, saying, “Rumors are started by haters, spread by fools, and accepted by idiots,” the Daily Mail reported. She also insisted that her boyfriend is the “finest, loveliest, tenderest, and most beautiful and brilliant person” she has ever known.
But that’s not the conclusion Burleigh arrives at in New York magazine. She doesn’t hold back in chronicling Trump Jr.’s personal challenges, as well as Guilfoyle’s baggage, in explaining why the former “MAGA diva” couldn’t fit, long-term, into his possible future as his father’s political successor.
On one hand, the former Fox News host became a successful fundraiser for Trump, starting in 2018 when she left Fox News and began dating his son.
Then again, she also is the ex-wife of California Gov. Gavin Newsom, one of Trump’s chief political enemies. But even after she, the former first lady of liberal San Francisco, proved her right-wing credentials as a Fox News host, she also left the network under a dark cloud. As Burleigh noted, citing a 2020 New Yorker report, Guilfoyle “distinguished herself as possibly the only female the company who was sacked for sexually harassing her staff.”
Still, Burleigh described how Guilfoyle took on an almost mentor role in Trump Jr.’s life after he divorced his wife, Vanessa Trump, the mother of his five children. Among other things, a friend told Burleigh that Guilfoyle handled calls from Vanessa Trump, seeking money in addition to her monthly alimony.
Yes, Guilfoyle was good at handling money and in making it, especially as Trump’s 2020 campaign finance chair, Burleigh reported. It also was reported that she went so far as to offer to give lap dances or share hot tubs with top donors.
Together, Guilfoyle and Trump Jr. became popular campaigners for Trump’s 2020 re-election efforts, “the prom king and queen of MAGA land,” as well as leading defenders of his “Big Lie,” — that he only lost that year’s election to Joe Biden because of voter fraud.
Guilfoyle was an eager participant at Trump’s Jan. 6, 2021 rally at the Ellipse, as Burleigh and others have reported. While she was angry that she wasn’t on the official speaker list for the rally, she still fought her way onto the stage and told the crowd, “We will not allow the liberals and the Democrats to steal our dream or steal our elections,” before Don Jr. told the crowd to “fight, stand up, and hold your representatives accountable.”
In a backstage video Trump Jr. took before his father sent his “patriots” to assault the Capitol, he recorded himself and Guilfoyle, as she boogied to Laura Branigan’s “Gloria,” displaying the sexy, hip-shaking dance she had been showcasing at other Trump rallies.
Following the “ignominious end” of Trump’s first term, Trump Jr. and Guilfoyle joined the rest of the family in leaving their long-time base in New York City and moving to Florida. Trump Jr. continued to find his “ticket to influence” through “the Big Lie,” Burleigh reported. As his father raised money for his legal defense fund and fended off one prosecution after another, Trump Jr. became increasingly popular as a “MAGA red-meat tosser by “spewing Biden global corruption conspiracies and shrieking about the weaponized deep state,” Burleigh added.
Trump Jr. also hid his “weak chin” under a beard and began to amplify voices “in the neofascist tech-reactionary world, radicalizing the MAGA-verse even more,” according to Burleigh. Most notably for Trump’s return to power, his son helped bring Elon Musk, J.D. Vance and other tech bro luminaries into his orbit, she said.
Before the election, the Daily Mail revealed that Trump Jr. had “blindsided” Guilfoyle with his “dalliance” with Anderson. By early December, it was confirmed that Trump Jr. and Guilfoyle had parted ways, shortly before Trump announced that he had appointed the former Fox News host to serve as ambassador to Greece in his new White House term.
A source told People that Anderson wanted Guilfoyle “out of the area” and dispatched across the Atlantic, as she began being seen with Trump Jr. at dinner in Palm Beach or at events for Trump’s inauguration.
Sources close to the Trump family have insisted that his split from Guilfoyle is “amicable,” while Burleigh said “the course was clear, in more ways than one,” for Trump Jr. “to jump to a new echelon.”