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For six years, Kimberly Guilfoyle and Donald Trump Jr. were pretty much inseparable. The former television news personality was so loyal to the first son that she earned a special spot within the Trump family and the trust of their patriarch, President-elect Donald Trump. However, now that Trump is close to returning to the White House, Guilfoyle has been replaced by Don Jr.’s new girlfriend, Bettina Anderson.
Anderson, the 38-year-old Palm Beach socialite, appears to have also grabbed the opportunity to work her way up within the Trumps’ circle and officially replace Guilfoyle, 55, not only as Don Jr.’s partner but also as the next pawn/lucky charm of Trump Sr. As a Trump loyalist, Guilfoyle previously served as the face of the returning president’s campaign. Now she’s been nominated by Trump to be the U.S. ambassador to Greece during his second term.
In a move that subtly suggests her desire to be noticed by the Trump patriarch, Anderson took to social media on Jan. 14 to show off the custom-made shoes she’s wearing to the inauguration on Monday, Jan. 20. The black velvet loafers she shared on her Instagram Story featured the embroidered letters “MA” on one shoe and “GA” on the other — forming Trump’s polarizing “MAGA” slogan for his political campaigns. To drive her point home, Anderson captioned the snap “custom perfection” and added an American flag sticker for good measure.
As if the photo wasn’t attention-grabbing enough, Anderson featured Klergy’s ominous track “And So It Begins” in her Instagram story to hint at Trump’s looming return to power. With this, it’s clear Anderson isn’t just dating Don Jr., 46, she’s also embracing the Trump family brand while seeking an opportunity to be part of the Trump administration. Back in December 2024, there was a rumor she was seeking a philanthropic role under her beau’s dad. So, as far as bold moves go, her recent post is practically a stomp. But then again there’s no guarantee that this would be enough to achieve what Guilfoyle did in Trump’s eyes.
Guilfoyle was by Don Jr.’s side for years. Her loyalty to him and his family cemented her as a vocal Trump family ally. She won the favor of the first family because she was faithful to them, and she remains a staunch supporter of Trump even if she’s no longer with his son. As Guilfoyle once reveled in the spotlight, Anderson’s rise has created a new dynamic that some may view as unsettling.
For Anderson, however, stepping into Guilfoyle’s shoes — if they’re not MAGA loafers, that is — hasn’t been without its challenges. According to sources, Trump himself is wary of Anderson’s influence on his son. “Donald Trump does not approve of his son’s association with Bettina,” a family insider revealed to Mediaite. “Bettina’s presence is seen as a liability rather than an asset.”
Inner-circle allies are also reportedly bracing themselves for Anderson’s appearance at the inauguration, a move some have described as a “potential misstep” that could forever cement her relationship with Don Jr. as a historical footnote.
Still, Anderson doesn’t seem fazed by the criticism. From her Instagram post alone, it’s clear she’s fully committed to supporting Don Jr. and the family’s controversial political machine. In fact, some speculate the custom MAGA loafers are just the beginning of Anderson’s efforts to cement herself as a permanent fixture in Trump’s world.
As for Don Jr., his choice to go public with Anderson has already fueled plenty of comparisons to his past relationship with Guilfoyle. The former Fox News host and staunch Trump supporter was known for her larger-than-life personality and full-throated defense of the MAGA movement. Anderson, by contrast, brings a younger, edgier vibe — though her penchant for partying has reportedly ruffled more than a few feathers among Trump loyalists.
Whether or not Anderson will win over Trump and his inner circle remains to be seen. For now, let’s say we’re excited to see what tricks she plans to employ next, especially with the inauguration just around the corner.