Kamala Harris And Kimberly Guilfoyle Have More In Common Than We Thought

Upon first glance, it's natural to assume that Kamala Harris and Kimberly Guilfoyle share anything besides their ongoing personal feud. With Harris being the former Vice President who boasts a storied career of public service and Guilfoyle having been involved with Donald Trump Jr. for nearly a decade, it's safe to assume the two are polar opposites. However, what many in the Bay Area will be quick to point out is that these two women share much more in common than the rest of the world might know. Considering they both got their start in San Francisco politics and worked their way to their current positions, more than just their timelines happen to overlap.

There's the obvious comparisons of wealth, with both Harris living a lavish life and Guilfoyle enjoying the finer things while she dated Don Jr. But now that both Harris and Guilfoyle are embarking on new paths after the 2024 presidential election, the similarities of their past, present, and potential future are stunning. Perhaps digging into what makes them so alike could help repair their relationship and ongoing beef — or it might just better explain why the two can't stand each other. No matter what, there's quite a bit to sink some teeth into. They're actually more similar than most people think — even them!

While it's pretty widely known that Kamala Harris got her start as district attorney of San Francisco — a position you need to have gone to law school to successfully snag — many might be unaware that this wasn't far from how Kimberly Guilfoyle began her own career. Not only did they both attend law schools in San Francisco, they also worked for the district attorney thereafter. Chilling, we know.

According to the East Bay Times, Guilfoyle attended UC Davis fresh out of high school before getting her Doctor of Law from the University of San Francisco. Guilfoyle used her earnings as a lingerie model to fund her way through law school, but this did not prevent her from securing her first job in San Francisco's district attorney office in 1994. However, her position was eliminated during some restructuring.

Harris, however, had a different experience during and after law school. After graduating from Howard University, she went on to attend the University of California College of the Law in San Francisco. Getting her start in the East Bay for the district attorney's office in Alameda County, Harris was eventually shuffled over and elected as district attorney of San Francisco in 2003. With an ongoing and mostly successful career in politics, her alma mater has been seeing quite the increase in applicants since her 2024 presidential run, per Reuters.

The early 2000s were full of quite the tumult for the city of San Francisco and beyond. After a quick stint in Los Angeles, Kimberly Guilfoyle chose to go back to the Bay in 2000 to be closer to then-husband Gavin Newsom. According to Medium, she was brought back into the district attorney's office as an assistant DA and in 2002 was part of the team that made national headlines. However, it was in 2003 that the feud between Guilfoyle and Kamala Harris began to take shape.

When Newsom was running for mayor of San Francisco, Harris herself was campaigning for district attorney. Per the SF Gate, Guilfoyle accused Harris of not being a true girl's girl and having hindered her own return to Bay Area politics. Harris has consistently denied this, and went on to win the election anyway.

Per Cap Radio, Harris also joined the San Francisco district attorney's office in 2000 and was put in charge of the Child and Family Service unit. It was here she made quite the name for herself by focusing on getting children who had been placed in the foster care system adopted into loving homes. Her old boss, Louise Renne, recalled Harris showing up with stuffed animals and treats on the days the courts would be placing children with new families, saying, "She knew [adoption day] was an important one and it should be celebrated."

Since Kimberly Guilfoyle's ex husband Gavin Newsom is known as the Governor of California, it can be easy to forget that in the early stages of their marriage, he was jockeying to be the mayor of San Francisco. In fact, that was part of the reason Guilfoyle relocated from Los Angeles was to help him run for and eventually settle in as mayor. Newsom was re-elected as mayor in 2007 before ultimately pursuing higher offices (it's long been rumored that he's got his sights set on the highest office in the land, so stay tuned for a presidential campaign to launch). But Guilfoyle isn't alone in dating a city politician — Kamala Harris also has a mayor as an ex.

Between 1994 and 1995, Harris and then-mayor of San Francisco Willie Brown were confirmed to be a couple. According to the SF Gate, when confronted with a bombardment of phone calls wanting his confirmation on their dating history, Brown responded in true form by saying: "Sure, I dated Kamala Harris. So what?" Their tryst happened back when Harris was an Alameda County assistant district attorney working in the East Bay. One of the larger scandals of the relationship was that Brown was still legally married to his ex-wife at the time, although they had been estranged since the 1980s. When it was reported in the SF Gate that Harris and Brown split in 1995, reporter Herb Caen wrote that it was a big surprise to most people, "including those who found Kamala Harris attractive, intelligent and charming."

After the first presidential debate between Donald Trump and Kamala Harris, the latter sat down with daytime TV powerhouse Oprah Winfrey to clear the air about some things. Trump had wrongfully claimed that Harris would want to take away firearms from law-abiding gun owners, and Harris was ready to call his bluff. In the livestream with Oprah, Harris divulged that not only was she a gun owner, but that "If somebody breaks into my house, they're getting shot." This came as quite a shock to many, especially since Harris was still running on a platform of wanting stricter gun control laws. According to the BBC, as much as Harris feels comfortable having a firearm in her residence, she is more skeptical of assault weapons being readily available and has lobbied for tougher background checks and implementing red-flag laws. Of course, she is not alone in her gun ownership.

While dating Donald Trump Jr., Kimberly Guilfoyle was quite the vocal advocate for her right to bear arms. In fact, one of the stranger things about their relationship was how intense Don Jr. was about having enough storage for his firearm collection. According to the New York Post, when they were on the hunt for their home, a source close to the couple claimed that "one of the first questions Don Jr. asked was where he could store his guns." Part of the compromise of purchasing the house Guilfoyle preferred in Bridgehampton was for Junior to construct a whole room dedicated to his original side-pieces. Although, now that they've gone their separate ways, Guilfoyle has remained quite mum about her gun ownership. Perhaps Don Jr. kept them all in the split.

As much as the night of the presidential election was a huge win for Donald Trump and his family, which was supposed to include Kimberly Guilfoyle, it ended up being full of heartbreak for the former Fox News personality. Shortly after declaring victory, Trump Sr. then broke up with Guilfoyle for Donald Trump Jr. by appointing her ambassador to Greece. Not only would she banished to halfway around the globe, but Don Jr. also soft launched his new flame, model Bettina Anderson, to the world just in time for her to appear at his side on Inauguration Day. As much as she might be trying to play it cool, insiders have mumbled that Guilfoyle is not taking the split well. Although, one could argue that Kamala Harris was dealt a larger heartbreak after the election.

After a resounding defeat, Harris went to nurse her wounds in Hawaii, causing a bit of a stir. Since then, she has certainly kept a low profile. She barely attended the inauguration ceremonies for Donald Trump and has been keeping her distance from prying eyes. While what's next for Harris is still a bit of a mystery, NPR revealed that she will be returning to California, but not her home city of San Francisco. Rather, the former Vice President will head to Los Angeles, where she'll continue to lay low while husband Doug Emhoff rolls up his sleeves to work at a law firm. Hopefully, the time away from the spotlight will do both Harris and Guilfoyle a bit of good.