Saturday, October 17th, 2026
I'll say one thing about KImberly Guilfoyle.
This Woman has led one Hell of an Interesting and Entitled Life so far.
Although these days it seems as though Kimberly is facing more Downs Than Ups it has not always been this way.
Kimberly started her life as the daughter of a rather well to do San Francisco businessman. Anthony Guilfoyle, who along with being Kimberly's dad was also, according to California Governor, Gavin Newsom's excellent Autobiography, "Young Man In a Hurry" one of Newsom's most trusted political advisors.
Even though Kimberly is not exactly ugly these days the Then and Now Photos of Kimberly clearly show that back in the day when she was married to Newsom for Four years she was nothing short of a Knockout - Extremely Beautiful.
These days- Eh, Not so much. She has obviously had some serious questionable plastic surgery resulting in puffy lips and what some people call "Mara Lago Face". Not Good.
Many years after living comfortably in Gavin Newsom's Liberal World, Kimberly Guilfoyle seemed to have had a complete change in Personality and World View and completely abandoned Liberal Society for the Comfort of Fox News, Donald Trump, Donald Trump Junior and Conservative Society.
Although Newsom certainly had a perfect opportunity in his book to trash his Ex he pretty much had fairly positive things to say about her. He did point out, however, that his mother and his sister were not particularly fond of Kimberly although they apparently did not express their reservations to Newsom early on. Newsom's sister indicated that she felt that Kimberly's need for attention was "over the top" and could never seem to be met to Kimberly's satisfaction.
Newsom and Guilfoyle cited problems with their long distance relationship as the main reason for getting divorced, although the fact that Kimberly was already pregnant with her next husband's child would have to be considered a factor in the downfall of their marriage. Kimberly was married to Eric Villency for Five Years after she and Newsom divorced.
Following her marriage to Gavin Newsom Kimberly began a career in television which was initially successful. She worked at Court TV and Fox News for awhile until problems cropped up with Fox News. She was apparently pressured into resigning after Fox News had to shell out 4 Million Dollars to an Assistant of Guilfoyle's at the network who accused Guilfoyle of Sexual Harassment and other improprieties.
Guilfoyle went on to date Donald Trump Junior and became an insider in the Trump Organization. She had some responsibilities regarding finances for the 2020 Re Election Efforts for Donald Trump.
Guilfoyle was even asked to speak at the 2020 Republican Convention which was essentially a Televised Convention Special due to Covid. Guilfoyle received a lot of Negative Attention for her Excessively Loud Convention Speech which some called "Unhinged". Clearly at this point things were going well for Guilfoyle and Donald Trump Junior. They were buying houses together and it was announced that they were engaged to be married.
Then something Happened.
What happened was the revelation in 2024 that Donald Trump Junior was now dating a Palm Beach Socialite named Bettina Anderson. who he has recently married in a controversial Ceremony largely paid for by a Russian Oligarch and close associate of Vladimir Putin.
Apparently as a Consolation Prize for getting cruelly Jilted in Public by the President's son, Donald Trump appointed Kimberly Guilfoyle to be Ambassador to Greece. Greece was certainly not a bad place to be sent when someone is trying to get rid of you.
But as was the case in other situations in which Guilfoyle always seemed to have self created problems with her jobs, it was revealed recently that while she was being considered for Confirmation to be Ambassador to Greece she was begging a Trump Donor named Eric Deter for 100 Thousand dollars to pay off her American Express Card and instructing him how to do it without leaving a paper trail that could be discovered.
Whoops, She did it again.
I'm sure that Kimberly Guilfoyle probably thought that this was no big deal. Within the Trump Klan 100 Thou is Chump Change to the Grifter in Chief.
But that is him, Kim, not you. You have to keep your nose clean and Grift from somebody who is not going to reveal your Grift to MSNOW.
There are, of course other allegations, as well, and as of today Donald Trump is searching for another Ambassador to Greece.
I wouldn't worry too much about Kimberly Guilfoyle, though. Now that she has joined the ranks of other Women dumped by Donald Trump like Kristi Noem, Tulsi Gabbard & Pam Bondi She will probably get a Tell All Book Deal from some publisher that will undoubtedly solve her financial problems for good.
And I'll be honest. I can't wait to read it.
I hope she will be as kind to Gavin Newsom in her book as he was to her in his book.
But to tell you the truth, I don't expect that to happen.
Sincerely Yours
Jerry Gallagher