Controversies on Kimberly Guilfoyle’s Relationship with Trump Jr, Her Divorce and Career Success

From an attorney to a news personality, politician, and the head fundraiser on President Trump’s re-election campaign team, Kimberly Guilfoyle’s career path has been quite remarkable. She has recorded some impressive achievements in this process and has received several accolades for her work.

Also quite remarkable about Kimberley Guilfoyle is the personal life that she has led. The former public prosecutor-turned-political aide has been married, and divorced twice, to some highly-placed individuals. That pattern of dating high-profile men continues as the media personality is now going steady with Donald Trump Jr., the first son of U.S. president, Donald J. Trump.

Ordinarily being associated with the Trump name is a given recipe for controversy but Guilfoyle takes hers to new heights with her further involvement in the president’s administration as well as his bid to get re-elected for a second term.

She and Trump Jr. Commenced Their Relationship Amidst His Divorce from Wife of 12 Years, Vanessa Trump

The romance between Kimberly Guilfoyle and Donald Trump Jr. began in early 2018 but the two have known each other for a while. The pair ran in the same New York social circles and became friends around 2007. They remained pals for several years during which Kimberly got closer to the Trump family. She ultimately became a part of Trump’s 2016 campaign and fervently promoted his candidacy at any chance she got.

All these brought her closer to Donald Jr. and by 2018, she and the businessman, who was in the midst of a divorce from wife of 12 years, Vanessa, commenced a relationship. The couple was first spotted together in April 2018 during a weekend of fishing in Montana. They later attended a party hosted for the American ambassador to Germany, Richard Grenell, in May 2018. They were also spotted together at the White House 4th of July party. The pair have been going steady since then and Kimberly has helped her boyfriend on the campaign trail for his father’s re-election.

As a sign of how serious things are between the couple, they jointly purchased a home in the Hamptons in July 2019. The quintessential cottage measures 9,200 square feet and is worth about $4.4 million. It features 7 bedrooms, 8 full bathrooms, and 3 half bathrooms over three floors. The relationship between Guilfoyle and Donald Jr. has received a stamp of approval from his former wife, Vanessa. In June 2018, a news article questioned whether the romance between Kimberly and Donald Jr. was not a conflict of interest for the latter. Vanessa retweeted the article and marveled at the lengths that people would go to attack a woman just because she is dating Don.

Kimberley Guilfoyle
Kimberley and Donald Jr.Image Source

The Couple have been Accused of Using Taxpayers Money for Private Expenses

Some critics have questioned whether Guilfoyle and Donald Jr. truly love each other or are just together for the purpose of achieving their future political ambitions. They rely on an analysis made by body language experts. According to these experts, the couple does not make any real effort to lean towards each other whilst doing interviews and public events. This, therefore, portends that they are focused on achieving their external need rather than pursuing their internal intimate romance. The experts have also pointed out that Kimberly and her man often avoid looking at each other in the eyes and don’t seem to take much of an interest when the other is speaking. Their relationship, therefore, appears to be more goal-oriented than about love.

Away from permutations, the couple has been mired in real-life controversies such as accusations of taking holidays at the expense of taxpayers. Back in July 2018, Kimberley and Donald Jr. took a two-day trip to Paris which reportedly cost the taxpayers about $64,000. This was to cover the costs of their $1000-a-night hotel room, flight costs, and protective armored vehicle rentals. Neither Kimberly nor her boyfriend is a government employee and this raised questions about why the government should be paying for a trip that was obviously for their own personal pleasure.

Another, and even weightier, scandal that the couple has faced is the sexual assault allegations against Kimberley. These allegations stemmed from her time at Fox News but only came to light in October 2020. According to a lady who worked as an assistant to Guilfoyle, the former public prosecutor often asked her to come work at her home and during this period, would often be naked. She would also go to the extent of showing her the pictures of male genitalia on her phone and would speak luridly about her sex life. The allegations did not stop at this juncture.

The assistant also complained that Guilfoyle exposed herself to her, urged her to trade sexual favors with highly-placed men, demanded a thigh massage on one occasion, and then tried to buy her silence with money when Fox commenced internal investigations. As one can expect, Guilfoyle strenuously denied these allegations. Her lawyers dismissed it as patently false while she herself maintained that in her 30 years of working in public prosecution, media and politics, she has never engaged in any workplace misconduct but rather serves as a mentor to countless women. This matter never made it to trial as Fox paid the assistant about $4 million to settle it out of court.

Kimberley Guilfoyle
With first husband, Gavin Newsom: Image Source

Her Marriage to Former San Francisco Mayor, Gavin Newsom, Crashed as a Result of their Busy Career Pursuits.

It is still early days in Kimberly Guilfoyle’s romance with Donald Trump Jr and as such, one cannot tell whether they would end up getting hitched. However, if they do, it won’t be the first trip down the aisle for Guilfoyle. The former Fox personality has been married and divorced twice and her first marriage was to former San Francisco mayor, Gavin Newsom.

Kimberly and Newsom tied the knot in a lavish ceremony held at the St. Ignatius Church in San Francisco in December 2001. The ceremony featured around 500 guests and was seen as a sort of launching for Gavin’s future political ambitions of running for the office of the mayor of San Francisco. He later won that election in 2003 and he and Kimberly became the first couple of the city overnight.

Several magazines scrambled over each other to capture them in glossy spreads and they were dubbed the new Kennedys as well as the Camelot couple. The couple was also wined and dined at several prime events in town and even played host to Prince Charles and Camilla when they visited the city. All of these gave off the picture of marital bliss but the couple ran into trouble after Kimberly landed a job to work as an analyst for Court TV in New York in 2004.

The long-distance between the east and west coast often meant that the couple could not spend any quality time together and things started going downhill from there. It eventually got to the point that they began leading separate lives and they filed for divorce in 2005. The pair attributed the split to their respective demanding careers and maintained that they still loved and respected each other, and would remain friends.

These sentiments proved true during their divorce which was finalized a year later in February 2006. The process was quite smooth and there was no wrangling over money despite the fact that they had no prenup.

Kimberley Guilfoyle
Kimberley with Eric and their son: Image Source

Her Second Marriage was to Furniture Heir, Eric Villency, in 2006.

Kimberly’s second husband is a famed businessman and TV host, Eric Villency. Eric is a native of New York City and the CEO of the Villency design group which deals in furniture and other interior design accessories. He has contributed as a writer to publications such as the New York Times and Huffington Post. He also hosts a weekly program, Idesign, on the Fine Living Network. Kimberly and Eric were introduced to each other by a mutual friend, famed photographer – Patrick McMullan, in 2005.

At that time, she was rebounding from her marriage and divorce from Newsom while Villency was coming out of a relationship with beauty boss, Olivia de Chantecaille. Such circumstances meant that the pair found a kinship spirit in each other and they soon delved into a relationship. That romance morphed into marriage a year later with the nuptials taking place at the Sandy Lane Resort in Barbados on the 27th of May 2006.

The couple’s union lasted for about three years during which they welcomed a son, named Ronan Anthony, on the 4th day of October 2006. They later called things quit in June 2009 with their divorce finalized that same year. The divorce process was also without a hitch as they had signed a prenup before getting married.

She Was Named Prosecutor Of The Month During Her Time As Los Angeles Assistant District Attorney.

Kimberly Guilfoyle began her career as an intern at the San Francisco district attorney’s office. During this period, she also moonlighted as a model for Victoria’s Secret and Macy’s. Fresh from law school in 1994, Guilfoyle found work as a prosecutor in San Francisco. Things then went sour in 1996 after a new sheriff, Terence Hallinan, came on board and had fourteen of the city’s prosecutors fired from office. One of them was Kimberley and she moved to Los Angeles to work as a Deputy District Attorney.

Guilfoyle would spend a total of four years in Los Angeles during which she worked on a wide range of cases including serious crimes such as domestic violence, kidnapping, narcotics, robbery, homicide, sexual assault, and arson. She carried out her responsibilities with outstanding dedication and won several awards including Prosecutor of the Month. This caused her profile to rise all throughout the state of California and the man who once fired her, Terrence Hallinan, rehired her to work as a prosecutor in the San Francisco District Attorney’s Office in 2000.

In her four years at the San Francisco office, Guilfoyle managed the trial division and once more stood out with her hard work. She made a name for herself with her role in several high-profile cases including People v. Noel and Knoller; a 2002 second-degree murder trial involving a dog mauling that garnered so much media attention within and outside the US. She also won several accolades including the outstanding woman of the year from the city of San Francisco. It was therefore with a sense of fulfillment and satisfaction that she decided to explore new career horizons in the year 2004.

Her time as a co-host of The Five: Image Source

Her Days as a Co-host and Analyst for Court TV and the Fox Network.

With the dawn of a new year in 2004, Kimberly Guilfoyle packed up her life in San Francisco and moved to New York in order to take up employment with Court TV. She then went on to spend two years with them during which she co-hosted Both Sides, a show that provides trial coverage as well as expert commentary on defense and prosecution perspectives. She also got to provide legal analysis for ABC News, Larry King Live, and Anderson Cooper 360°.

All of these helped to raise her profile nationally as she covered major legal cases such as the trial of O.J. Simpson for the murder of his wife; the trials of Kobe Bryant and Michael Jackson for sexual assault; the murder of child pageant queen, Jon Benet Ramsay; as well as the trial of California man, Scott Lee Peterson, for the murder of his pregnant wife and unborn child in 2004.

After two action-packed years at Court TV, Kimberley Guilfoyle was hired by Fox in January 2006. Her first gig at the channel was to host the one-hour crime-based weekend show, The Line-Up. From there, she went on to become one of the co-hosts of The Five, a one-hour talk/debate show. Overall, Guilfoyle would spend about 12 years at Fox during which she occasionally stepped in to host shows such as Outnumbered, Hannity, and Fox and Friends, etc. She also lent her legal expertise to other shows on the network’s line-up including The O’Reilly Factor.

She is the Head Fundraiser for Donald Trump’s 2020 Re-election Bid.

Kimberly Guilfoyle was part and parcel of the campaign team that midwife the victory of Donald Trump in the 2016 November general elections. Following that victory, she was touted as a potential press secretary but that position never materialized. Despite that disappointment, she has remained loyal to Trump and now serves as the head of the fund-raising division for his 2020 re-election bid. In this role, Guilfoyle has spoken at several campaign events in different states across America.

She was also one of the first speakers at the Republican National Convention in August 2020. During the speech, she blasted the radical and socialist agenda of the Democrats for wanting to destroy the country and take away everything that was hard-fought and won. She also accused them of wanting to steal people’s liberty and freedom. For Trump, Kimberley had only words of praise. She described him as the law and order president, stating that he had created the greatest economy the world has ever seen. This speech impressed the conservatives but the liberals derided her on Twitter with many describing it as dictatorial.

Guilfoyle delivering a speech at the RNC: Image Source

Guilfoyle Penned the 2015 Self-Help Book, Making the Case: How to Be Your Own Best Advocate.

In 2015, Guilfoyle published her first book, Making the Case: How to Be Your Own Best Advocate. The book draws from her experience as a prosecutor and arms readers with tips on how to organize their thoughts and plans, have meaningful discussions with the people around them, and achieve their life goals.

The self-help book also relies on Guilfoyle’s own personal experience to teach readers that they can achieve anything they set their minds to. As the child of Puerto Rican and Irish immigrants, Kimberley did not have it easy growing up. Her situation was further complicated when her mother died and she had to take care of her little brother. Despite all these, she effectively pursued her studies and rose to become what she is today.

The prosecutor thus preaches to people that they can pursue and accomplish anything they want and blaze a trail for other people to follow. She also wants them to understand that occasional setbacks do not define them as failures. The book received glowing reviews with Forbes describing it as a friendly and generous effort by an ambitious, competitive, and compassionate person to share what has worked for her.

Steve A
Steve A
An award-winning writer and journalist with several years of experience – this author can turn dreams into reality on paper and can bring color back into a sometimes static landscape


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