As the Trump team ratchets up its attacks on presidential opponent Kamala Harris, one member of the Republican candidate’s camp has been particularly vitriolic.
Donald Trump Jr’s fiancée and Trump campaign firebrand Kimberly Guilfoyle has recently flooded the airwaves and social media blasting Harris as a ‘fraud on every level’, a ‘DEI hire’, and a failed prosecutor who ‘supports anarchy, literally.’
She joins the numerous Republicans who have publicly bashed Harris’s bid for president since she became the presumptive Democratic nominee following Joe Biden’s withdrawal last month.
But DailyMail.com can reveal that Guilfoyle’s animosity towards Harris goes beyond their political differences and appears to stem from a years-long grudge dating back to when they were working in the San Francisco District Attorney’s Office.
The feud began in the early 2000s after Guilfoyle, a local prosecutor, accused then assistant district attorney Harris of trying to block her from returning to her previous job with the DA.
Trump campaign supporter Kimberly Guilfoyle’s scorn towards Kamala Harris appears to go beyond politics and opposing parties, DailyMail.com can reveal
Long before Harris became a Republican adversary and opponent to Guilfoyle’s presidential candidate, Donald Trump, the pair had worked as prosecutors in the San Francisco, where Guilfoyle’s then-husband Gavin Newsom was mayor. They are pictured volunteering in 2004
Guilfoyle has recently flooded the airwaves and social media blasting Harris as a ‘fraud on every level’, a ‘DEI hire’, and a failed prosecutor
The falling-out even made the local paper in a 2003 column for the San Francisco Chronicle headlined, ‘Brains, brio, beauty – and wounded feelings.’
Speaking to the Chronicle at the time, Guilfoyle slammed Harris for the ‘frosty and underhanded’ treatment she got from her superior.
‘The bottom line is she didn’t want me there,’ she said.
People who knew them as colleagues working together at the DA’s office in 2000 when Guilfoyle was dating future husband Gavin Newsom, were not surprised to see Guilfoyle reviving an old rivalry.
Now Don Jr.’s fiancée, she’s spent recent days stepping up attacks on her former nemesis who’s now pursuing the nation’s highest office.
But Guilfoyle’s early aughts’ critique of Harris, pales in comparison to today’s assessment.
‘KAMALA HARRIS IS A FRAUD ON EVERY LEVEL,’ reads one posting on Guilfoyle’s Instagram account, which also features her laughing and agreeing with former President Donald Trump’s assessment that she ‘became black’ only later in life.
According to the 2003 column, Guilfoyle was ‘still smarting’ from the perceived slight three years earlier, when she was looking to move back to San Francisco from Los Angeles to be with Newsom, her then boyfriend who was city supervisor.
‘You have to understand, I came with an excellent resume, and talented women should support other talented women,’ Guilfoyle told the paper at the time.
She still managed to muster some kind words for Harris who was running for San Francisco DA.
Guilfoyle lost her job at the district’s attorney’s office in the mid-1990s after District Attorney Terence Hallinan (left) was elected and cleaned house. It was under Hallinan’s tenure that Harris (pictured right in 2003) joined the DA’s office
Guilfoyle had been dating first husband Gavin Newsom at the time and ended up taking a job with DA’s office in Los Angeles after the shake up
Guilfoyle called her ‘very smart’ and a ‘good speaker’ who ‘will work very hard’ if elected, The Chronicle reported.
Andrew Ross, one of the two Chronicle journalists who reported the story, told DailyMail.com this week that Guilfoyle and Harris were ‘two ambitious women vying for prominence in San Francisco’s political pond and that included high society.’
Guilfoyle, a San Francisco native, was working in the district attorney’s office in the mid-1990s but lost her job when newly-elected District Attorney Terence Hallinan cleaned house to bring in some of his own employees.
So Guilfoyle took a job with the district attorney’s office in Los Angeles.
Around that time, Harris was a rising star in the nearby Alameda County District Attorney’s Office in Oakland, alongside powerful boyfriend Willie Brown, the then-Mayor of San Francisco and former speaker of the California State Assembly who appointed her to two state commissions.
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Hallinan’s chief assistant Richard Iglehart later recruited Harris in 1998 to supervise the district attorney’s career criminal unit, the Chronicle reported.
It wasn’t until Iglehart left in 2000 and local lawyer Darrell Salomon took his place that Guilfoyle began reaching out to staffers about returning to the Golden City.
‘During that time, Kim called me,’ said Paul Henderson, a longtime friend and former colleague of Guilfoyle’s in the district attorney’s office.
‘She was making calls to everyone, saying, ”I’m trying to come back. Can you help me? Can you say positive things?’
‘Kamala was a much more senior lawyer at the time,’ Henderson explained. ‘Either Kamala didn’t return the call or didn’t get excited about it and be like “Yeah girl, for sure, let me make some calls, let me talk to Terrence.”
He said Guilfoyle, in speaking about Harris, would tell him, “She doesn’t like me. She didn’t want me in the office, and she tried to block me.’
Around that time, Harris was a rising star in the nearby Alameda County District Attorney’s Office in Oakland, alongside powerful boyfriend and mayor of San Francisco Willie Brown (pictured)
Harris would eventually run for San Francisco DA and get elected in 2003. She is pictured being sworn into office in January 2004
Then San Francisco Mayor Gavin Newsom is seen walking with newly elected San Francisco District Attorney Kamala Harris in 2004
As Guilfoyle explained to the Chronicle in 2003, Harris became aware of Guilfoyle’s plan and retrieved her resume.
‘She called me and said basically that she was on the hiring committee and in charge of the budget for the DA’s office, and that I should have gone through her if I wanted to return to the DA’s office – and that there was no money to hire me.’
Guilfoyle told the Chronicle she then called the office to find out that there was no such hiring committee, and that Harris had no say in the matter.
The Chronicle also spoke with Harris, who shared a different version of what happened.
‘I never discouraged her from joining the office,’ she told the paper. ‘I never suggested to her that there wasn’t a job for her in the San Francisco DA’s office – of that I’m very clear.’
She acknowledged she called Guilfoyle in LA, but said it was ‘to see if she needed any help.’
Guilfoyle did land a job in the office a few months later.
In the 2003 column, when Harris was running for district attorney, she uderplayed the drama.
‘I’ve seen Kimberly a number of times over the last few months,’ Harris told the Chronicle. ‘We have a great rapport and have great respect for each other.
‘I think she is a great lawyer, and I look forward to working with her,’ Harris added.
Guilfoyle, who would eventually leave the district attorney’s office to work on her husband’s campaign in 2003, accused Harris of trying to block her from returning to her old job
These days, the two women are further divided by their politics. Guilfoyle would eventually divorce Gavin Newsom, now the Democratic governor of California, pictured with Vice President Harris in 2018
Meanwhile, Guilfoyle has crossed over to the right and is now engaged to marry Donald Trump Jr and is a major player in Trump’s campaign
Speaking to DailyMail.com, Ross, even as the author of the column, admitted that he didn’t know who to believe.
‘Exactly whose version of events was true was almost less relevant than the fact that there was a real rivalry and jockeying between them for recognition,’ he said.
Guilfoyle would eventually go on to leave the district attorney’s office around that time to go work on her husband’s campaign, before moving to New York to become a legal commentator on Court TV, CNN, and Fox News.
She and Newsom divorced in 2006.
After another marriage and divorce, she became engaged to Don Jr. in 2018.
Since her San Francisco days, she’s become a Trump firebrand, rallying crowds at the Republican National Convention and promoting the campaign on cable TV and social media.
Harris, who rose from district attorney to California attorney general to the U.S. senator and then President Joe Biden’s VP, is now the Democratic nominee for president.
Ross told DailyMail.com he finds it surreal but also not so surprising to see Guilfoyle taking off her gloves in the renewed battle against Harris two decades later.
Guilfoyle hasn’t been shy about expressing her disapproval towards Harris, often sharing memes and anti-Harris content on Instagram
In one scathing Instagram post, she blasted Harris for her ‘dangerous policies and failed leadership’
‘Who’d have thunkat the time that this rivalry would one day be center stage in an American election, with Kamala running for president and Kimberly as Don Jr.’s fiancé and a major player in Trump’s campaign.’
Paul Henderson, former chief of administration in the DA’s office, said he remains close with Guilfoyle, even if he is a steadfast Democrat who previously served as a policy advisor for the Biden campaign.
‘Kimberly and I are good friends,’ he said. ‘We had the same modeling agent in high school. We shared an office in the DA’s office for several years, and I’ve continued to be her friend. We just don’t talk politics anymore.’
Knowing both women, Henderson said, he believes the two secretly respect each other.
‘I know Kimberly’s not a fan, obviously,’ he said. ‘I see all her stuff. But I maintain my own cognitive dissonance in being her friend.
‘I think she’s in a tough spot,’ he added. ‘I mean, what can she say? She can’t be neutral on this.
‘I think Kimberly has a role to play and she’s playing it. She’s got to be an advocate. And she’s a very good lawyer, she really is. I still like her and respect her.’