It did not take long for President Donald Trump’s son, Donald Trump Jr., to move on from his wife Vanessa Trump since the pair filed for divorce in March. Trump Jr., like his father, has an eye for beauty and brains which explains why the news of him dating one of the most stunning beauties on Fox News is not shocking.
Sources told The New York Post’s Page Six that Trump Jr. has been dating Fox News’ “The Five” co-host Kimberly Guilfoyle. The sources said that the pair has been dating for weeks as Trump Jr.’s divorce proceedings are progressing.
On Sunday, the new couple arrived together for a party for President Trump’s new ambassador to Germany, Richard Grenell. The party was also attended by Fox News personalities Dana Perino, Martha MacCallum, Harris Faulkner, Kimberly Guilfoyle, and Greg Gutfeld. However, Guilfoyle was the only one of them to arrive with Trump Jr., Page Six reported.
Trump Jr. also toasted Grenell, who had a tough and long battle to get confirmed for the position. “I look forward to you [Richard] going there, because every time . . . I read about what is going on there and everywhere else, I don’t know if I’m reading a newspaper or if I’m reading the Onion. I look forward to seeing someone who is not afraid to speak up and fight for what’s right,” he said. “And I look forward to visiting . . . As long as they don’t say I am somehow colluding with the Germans.”
Trump Jr. and Guilfoyle stuck by each other the entire evening and then left together and went to dinner at Harry Cipriani on Fifth Avenue, Page Six reported. And for Guilfoyle, this is far from the first high profile relationship she has had.
Prior to coming to Fox News, Guilfoyle was the first lady of San Francisco as she was married to the city’s mayor and current California Lt. Gov. Gavin Newsom, who is a Democrat. And last year she was linked to former White House communications director Anthony Scaramucci. At the time, Page Six reported that the pair were dating, but sources close to the pair contested that.
A source close to Scaramucci said that the two were “just very good friends who enjoy each other’s company . . . It is too early to call them a couple. He is busy establishing his post-White House career.” This is a sentiment echoed by a source with ties to Guilfoyle.
“Kimberly thinks the world of Anthony. He is one of her best friends, but they are not a yet a couple. He is still going through a divorce. She is a single mom, and her son is her priority,” the source said. Representatives for both did not comment on the story.
Trump Jr.’s estranged wife Vanessa also had her share of interesting relationships too. Vanessa, known by her maiden name Haydon, was linked to movie star Leonardo DiCaprio in 1998. Page Six reported at the time that “DiCaprio’s luscious love is 20-year-old fashion model Vanessa Haydon. The passionate pair have been inseparable over the past two weeks,” it wrote. The pair “tried to keep a tight lid on their budding romance — but it all spilled out during a private party in a trendy SoHo loft last week … The couple could be seen holding hands, kissing and cuddling into the wee hours in a dimly lit corner.”
And before that, she was linked to a member of the Latin Kings gang, Valentin Rivera, who did several stints in prison. Rivera has done time for assault, weapons offenses, and negligent homicide, Page Six reported.
Rivera was a tough gang leader, but he had a soft spot for Vanessa, and he would do anything to defend her. “If anybody disrespected her in any way, I would physically put my hands on them,” Rivera said. “Any types of disrespect — call out her name, mess with her, anything,” he told Page Six.
The pair’s relationship was interrupted when Rivera was arrested and given a 1 1/3-to-four-year prison sentence. “She was heartbroken that I was being taken away,” Rivera said. “The first time [she came to visit], she was upset — she cried a little bit — but after a while, we get used to things. She only came to visit me twice because her mother forbid her from coming to visit me.”
The women in Trump Jr.’s life have interesting histories. But it is the burgeoning relationship with the newest, Guilfoyle, that could be the most interesting. Could you imagine what other media networks will do if the two get closer or if they get married? CNN shows its jealousy of Fox News now. It will be off the charts if this relationship grows. Who knows, they could even accuse Trump Jr. of colluding with her.