Shadow Campaigns and Old Flames: Could Guilfoyle be helping Newsom?
Guilfoyle maybe a conservative darling but could she be giving ex-husband Newsom an assist hoping to take out DeSantis?
In case you aren’t aware, the governors of California and Florida are about set to go mano-a-mano in a debate tomorrow moderated by Fox News long-time host Sean Hannity, and many people are asking, “But why?” Including me.
I posed this question on my Instagram stories with the following commentary:
“What annoys me is that Newsom is clearly running a Presidential shadow campaign, likely with the blessing of the DNC.
This (debate) helps Newsom with his shadow campaign. Honestly, Desantis should ignore him. He (Newsome) isn’t even well-liked.
It comes off a little desperate and gimmicky on both sides.
Just focus on your campaign, Ron!”
Later that night, while I was sleeping, I received a voice memo from a source with a conspiracy theory that piqued my interest, and I thought it would be fun to work out with you all here.
Mind you, my only source is this voice memo, my research, and my speculation. This is not a hard new investigative piece. This is fun speculation. However, if anyone has some supporting information, please send it my way.
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So, what is this conspiracy theory I got in the middle of the night?
In a nutshell. Is Newsom getting an assist from Don Jr.’s former Fox News Host, Irish-Puerto Rican fiance and ex-wife Kimberly Guilfoyle? Who, by the way, has deep roots in San Francisco Democrat political circles.
To thoroughly explore this theory, we must go back in time to Guilfoyle's roots in California Democrat politics and her long history with her ex-husband, Gavin Newsom.
Gavin and Kimberly sitting in a tree
In the glamorous world of political power couples, few stories sparkled in the early 2000s, like that of Gavin Newsom and Kimberly Guilfoyle. The San Francisco Chronicle dubbed them as the next "liberal power couple" after their lavish 500-guest wedding in 2001.
When Gavin was elected Mayor of San Francisco, Harper's Bazaar featured them in their September 2004 issue titled "The New Kennedys."
The seven-page fashion spread allowed Guilfoyle to flaunt her former modeling skills while the feature told their tale of love reminiscent of a modern-day fairytale.
Gavin meets Kimberly
It all began at a Democrat political fundraiser in one of Newsom's chic San Francisco eateries, a setting befitting a man who, alongside best pal Billy Getty (Yes, as in Getty Petroleum and Getty Images), had already made a splash in restaurants, real estate, and wineries before diving headfirst into the political pool at the ripe age of 29.
Kimberly, then a bright spark at the Los Angeles DA's office, recalls that first electrifying moment:
"I looked across the room and saw Gavin—tall, elegant, handsome, charismatic."
And Gavin? He was equally smitten, describing Kimberly as "beautiful and bright." But it wasn't just her looks that captivated him. No, it was her "belief in people and their power to be expressive." A mutual admiration, yet love was put on hold because they were both involved.
Newsom reminisces, "I was always asking, 'Whatever happened to that DA from LA?'"
Sidenote: Gavin and Kimberly were likely in the same circle and often saw each other before they were officially a public couple. She was involved with Gavin’s buddy and business partner, Billy Getty, before Gavin. San Francisco gossip columns at the time pointed out that Newsom’s long-time friend and business partner were on the outs by the time Gavin and Kimberly married. Did Kimberly come between old friends?
Why was Kimberly Guilfoyle, a name now synonymous with conservative circles, at a Democrat political shindig?
Guilfoyle’s Democrat family roots
Enter Anthony "Tony" Guilfoyle, Kimberly's dear old dad, who wasn't just any San Francisco socialite but a kingmaker in San Francisco political circles.
Tony immigrated from the Irish town of Ennis, County Clare, in 1957 and was drafted into the U.S. Army during WWII, achieving the rank of sergeant while stationed in West Germany in the late 1950s
After the war, he returned to conquer San Francisco. In San Francisco, his business focused on the construction and real estate industries before rising to prominence in local politics as a founding member of the San Francisco Coalition for Responsible Growth, where developers and real estate bigwigs pulled the strings.
Tony was a pivotal player in the rise of Gavin Newsom before and after he and Kimberly married. During Newsom's political ascent, Tony wasn't just a casual bystander but a key strategist, weaving his magic in Newsom's campaigns for the San Francisco Board of Supervisors and his mayoral run in 2003. His behind-the-scenes mastery earned him the nickname “Godfather” of San Francisco politics.
Sadly, Kimberly’s father passed away in 2008 from cancer. But that does not mean the Guilfoyle influence in California's political landscape just vanished into thin air.
Enter Tony Guilfoyle Jr., Kimberly's low-profile brother. While Kimberly was busy making waves as a conservative firebrand, Tony Jr. appears to have maintained his Democrat roots by quietly donating to California Democrats.
How do I know? Because he wrote checks to the tune of $2,500 for Newsom's 2018 gubernatorial campaign and slipped $500 into Act Blue California's coffers as recently as 2021. Interestingly – since 2021, Tony Jr.'s trail of donations has gone cold. Oddly, his public donations dried up about the same time his sister became more involved with Trump. Maybe he stopped donating, or he switched to dark money donations (you know, those sneaky 501(c)(4) contributions) as an undercover favor to his sister? I guess we will never know.
“Gavin, It’s not you. It’s me.”
In January 2005, one year after Kimberly stood by Gavin's side as he was sworn in by his father, Judge William Newsom III, as the Mayor of San Francisco and less than four months after a glamorous feature in Harper's Bazaar that referred to them as "The New Kennedys," Jackie filed for divorce from her tall, dark, and handsome husband Jack.
The main reason cited for the separation was the strain of having careers on opposite coasts. You see, Kimberly had started her career as a television host on Court TV in New York City at the time, leaving Gavin all alone in San Francisco with his wine and hair gel.
Kimberly and Gavin’s love may not have stood the test of time, but as they said in their joint statement, "We are committed to remaining friends and will continue to support each other in our respective careers."
Fast forward, and both have new love stories. Gavin went on to marry filmmaker Jennifer Siebel and have four children. Meanwhile, Kimberly moved on with businessman Eric Villency and has one son. But she and Villency called it quits in 2009.
Cue the plot twist: 2018 saw Kimberly making waves by stepping out with none other than Donald J. Trump Jr. She would later become a staple in the Donald Trump 2020 Presidential campaign.
Ok, so clearly, the once golden couple of San Francisco have chosen diverging political paths and allegiances. Newsom ascended to the throne of California's governorship, becoming the Patrick Bateman of Democratic politics with his dinners at The Frech Laundry (during the state-imposed COVID lockdown) and attendance at a Getty wedding.
Meanwhile, Guilfoyle went from San Francisco Democrat darling to landing a spot on Fox News's "The Five," getting engaged to Donald Trump Jr. and becoming a staple in the Trump and conservative politics world. Talk about a 180-degree turn!
We can be friends
The thought of Newsom and Guilfoyle staying chummy post-divorce seems as likely as snow in July, right? Well, it's a classic case of 'yes, but actually no'.
Yes, by 2018, she's entrenched in Trump's camp, heading a pro-Trump super PAC and dating Don Jr., the poster child for trolling liberals. But that same year, Guilfoyle told WaPo a recent story of her on the phone with Newsom, jokingly threatening to unleash Don Jr. on his gubernatorial campaign. And then, just for giggles, she puts Don Jr. on the phone with Newsom, and the two men end up chatting about... hair products!
“Gav’s hair is slicked back,” she explains helpfully, “and Don’s hair is slicked back.”
Admittedly, things appear to have gotten a tad frosty following her 2020 RNC screech….er speech. She took some not-so-subtle jabs at California, painting it as a dystopian nightmare under Democratic rule.
Newsom refrained from mudslinging when asked for his take on Guilfoyle's fiery RNC speech. Although, three years later, he did say on CNN's "The Axe Files" podcast that the Kimberly he knew back in the day had “fell prey” to the Fox News influence.
So, are these two political opposites still on friendly terms? It's hard to tell, although my source says she has it on good authority that they still are chummy.
Newsom for President?
Newsom has long had his eye on the presidency. Sure, he plays coy, claiming he fully supports Biden as president, but let's be real, we all know he was disappointed after Biden's team resorted to using the short stairs for Air Force One exits after a few oopsie-daisy moments.
Newsom has been running a shadow campaign for well over a year. He has used re-election campaign funds to put up billboards in South Carolina and six other states, advertising the availability of abortion in California. There have also been multiple news stories, which seem to be fueled by the governor's allies, suggesting that he is ready to run for president as soon as the Democratic nomination becomes available.
Then there was the COVID saga, with Newsom and DeSantis turning their states into stages for their pandemic performances. Comparing red state Florida to blue state California, and news flash, California was losing.
Guess what? Newsom did not like the comparisons, so over the summer of 2022, he threw shade at Florida with ads saying, “Join us in California, where we still believe in freedom,” in an attempt to take jabs at Florida’s parental rights laws. A laughable statement, by the way, from a governor who pushed some of the most draconian COVID restrictions in the nation.
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Debate me, bro!
But, ever the showman, before DeSantis even announced his run for president, Newsom called for a debate throwdown.
Florida Governor Ron DeSantis announced his candidacy for the 2024 presidential election on May 24, 2023, during an unfortunately very glitchy Twitter/X Space. Then, unexpectedly, just three weeks later, Gavin Newsome ventures into “enemy territory” for an hour-long interview with none other than Guilfoyle's friend Sean Hannity, where Hannity pitches him a DeSantis-Newsom debate.
Hannity and Newsom’s bromance
I watched Hannity’s entire interview with Newsome, and I have thoughts! First, there were clearly bromance sparks flying.
To the untrained eye, some might think this interview was a combative engagement, but what I saw, between Hannity’s compliments of Newsom and Newsom’s creepy chuckles, was a friendly sparring between admiring friends.
Hannity, known for skewering California's liberal policies, seemed to be lobbing softballs rather than hard-hitting critiques at Newsom. Every challenge from Hannity was batted away by Newome, bombarding Hannity with stats that he was ill-prepared to retort.
Was this a case of Hannity being underprepared? It hardly seemed like it. The man's a pro, and he didn't look one bit flustered. So, was he perhaps doing a friend a solid? The other question is the friend Newsom or Guilfoyle?
Hannity's interviewing performance was, let's say, less than rigorous. Barely a challenge and fact-checking? Non-existent. Meanwhile, Newsom was dishing out carefully curated stats with that unnervingly wide smile, so skillfully he almost convinced me that California's economy is booming and that he's the #1 governor.
The bromance bloomed even more during Hannity's cozy chat with Newsom after the Republican primary debate.
We just hit it off.
I thought I might be seeing things, but then Hannity spills the beans to the Los Angeles Times: “We just hit it off.” He's practically singing Newsom's praises, reminiscing about their easy rapport and fun banter, "Oh, come on, you don’t believe all that," he says about their interactions.
Their buddy-buddy dynamic dates back to when Newsom would pop into the Fox News studio in Manhattan to visit his then-wife, Kimberly Guilfoyle.
“I can’t give you a date or a specific memory,” Hannity said of his first time meeting and getting to know Newsom, according to Politico.
“All I do remember is that on a personal level, he’s extraordinarily personable. Just like Governor DeSantis is.”
“We hit it off. We just kind of hit it off. I respect both people at a very high level. I really do,” Hannity said.
Glamorous Political Duo: Kimberly Guilfoyle and Gavin Newsom, once hailed as the next "liberal power couple" by the San Francisco Chronicle, tied the knot in 2001. Following Newsom’s mayoral 2005 win, Harper's Bazaar dubbed the pair "The New Kennedys."
Family Ties in Politics: Guilfoyle's father, Tony, a key figure in San Francisco politics, played a significant role in Newsom's rise in San Francisco politics, ultimately guiding him to his mayoral seat, earning the moniker “Godfather” of local politics.
Brother's Democrat Connections: Tony Guilfoyle Jr., Kimberly's brother, appears to maintain ties with California Democrat politics after his father passed and his sister positioned herself as a Republican talking head, evidenced by his donations to Newsom's 2018 gubernatorial campaign and to Act Blue California in 2021.
Guilfoyle's Shift to Conservatism: Post-divorce, Guilfoyle transitioned from a San Francisco Democrat to a prominent conservative figure, joining Fox News and later becoming engaged to Donald Trump Jr.
Continued Connections: Despite their political and personal divergences, Guilfoyle and Newsom are rumored to have maintained a cordial relationship.
Newsom and Hannity: A friendship appears to have blossomed between Newsom and Hannity, rooted in their past relationships with Guilfoyle.
Tin hat time
Gavin and Kimberly seemed to be all buddy-buddy post-divorce until Guilfoyle's 2020 RNC speech threw shade at California, sparking rumors that their amicable ties might have hit a snag.
But let's not forget, they played the friend card WAY longer than they've been on the outs, and word on the street is they're still on friendly terms; how cozy they really remain is up for debate. But when ambition comes into play, who's to say old flames of friendship can't be fanned by mutual self-interest?
What about Hannity? Why would he help? Why not? He’s been supportive of Trump, and maybe an old friend made a phone call with a request and a nudge for a favor. Besides, it helps his profile and ratings.
Anything is possible when you combine a long history, continued political ties, ambition, and mutual interests. So what are these 'mutual interests' that could potentially have Newsom and Guilfoyle scratching each other's backs:
Yes, Trump is leading the Republican polls, but he has made it clear he's no fan of "DeSantimonious," and polls are as stable as a house of cards in a windstorm. In Iowa, Trump's ahead, but DeSantis is nipping at his heels in other surveys. And Nevada? It's a political roulette! So, could Guilfoyle be pulling the strings for a Newsom-DeSantis debate showdown, hoping DeSantis will fall on his face? After watching Newsom spar with Hannity, it looks like Newsom has some debate chops, while Desantis' latest debate performances have been “meh,” and let's be honest, DeSantis is awkward.
Trump's camp is betting that Newsom 2024 for President will not materialize. They're banking on Biden staying in the race, and even if Newsom did throw his hat into the ring, they reckon he'd be easy pickings, what with California's mixed bag of a record. But let's not kid ourselves; Trump's national appeal isn't exactly rock-solid either, so it's a risky bet.
And then there's the VP angle. Newsom might be eyeing a sidekick role, given everyone's literal nightmare is VP Harris becoming president. If he waltzes into the VP spot, he's just a stumble down the stairs from the top job. Plus, let's not forget Guilfoyle's no fan of Harris, dating back to their DA days.
That’s it. That is the conspiracy theory. From their early days as the "New Kennedys" to their divergent paths post-divorce, their connections are prime for speculating blurred lines between personal relationships and political maneuvering. Let’s not forget Guilfoyle’s deep Democrat roots, the rumored cordiality between Guilfoyle and Newsom despite their political polarities and the intriguing dynamic between Newsom and Sean Hannity.
Now, let's turn to you, the readers. What's your take on this theory? Do you see threads of truth in the speculated alliances and strategies, or is my tin foil hat on too tight? Did I miss anything? Do you know something I don’t know?
Share your thoughts in the comments below.
As for a predictive analysis of the upcoming Newsom vs. DeSantis debate, it's a high-stakes game. In a time where clap-backs and clip-able soundbites often determine political winners. With his charisma and polished public persona, Newsom may have an edge. On the other hand, DeSantis often comes across as more reserved and awkward, but if he leans into success in Florida, he could eke out a positive performance.
The debate will likely benefit Newsom more, providing him with a national platform to bolster his potential presidential aspirations. If DeSantis doesn’t perform, it could have a significant negative impact on his already anemic campaign, benefiting not only Newsom but Trump. Can DeSantis manage to outperform expectations, solidifying his position as a leading figure in the Republican Party?
Who will come out on top? That remains to be seen. Will you be watching?