Does Donald Trump like his yes-men a little on the unusual side? Or why is his GOP running mate JD Vance wearing mascara? Is it just those baby blues that make it look like he’s got Hillbilly Elegy eyeliner on all the time or is there more?
IONCE ATTENDED A party in New York City, where its then-mayor Rudy Giuliani in a gorgeous platinum blonde wig styled by RuPaul was made up as a Marilyn Monroe and at one point business tycoon Donald Trump was seen seemingly hitting on the striking but oversized former federal prosecutor.
There are certain mysteries in life that remain unsolved, like the Bermuda Triangle, the disappearance of Amelia Earhart, and why Donald Trump prefers his yes-men a little on the unusual side. It seems the former President has an affinity for the unconventional, whether it’s in their advice, their loyalty, or their penchant for makeup.
Let’s consider the case of his GOP running mate, JD Vance. Rumors abound that Vance, author of Hillbilly Elegy and apparent mascara enthusiast, is taking his style cues from an unexpected source. Is it true that his baby blues are accentuated with eyeliner, or does he just have a knack for looking like he’s always ready for his close-up?
Me, I have nothing against seeing JD Vance wearing Hillbilly Elegy eyeliner, though I’ve usually worn it with shocking Yves St. Laurent Shanghi Red lipstick matching the soles of my Christian Louboutin 4-inch pumps. I mean, I’ve stilettoed my way across the tightrope of America, too, just not into the United States Senate chambers.
As I pondered this curious phenomenon, I couldn’t help but recall that party in Manhattan. It was one of those grand affairs where the glitterati of Gotham gathered to outdo one another in ostentatious displays of wealth and eccentricity. Amid the sea of designer suits and little black dresses, one figure stood out like a sore thumb — or rather, like a six-foot-tall federal prosecutor in drag. The scene was unforgettable.
Rudy Giuliani had transformed himself into a stunning platinum blonde with a little help the biggest drag queen in America. Giuliani was dressed to the nines as Marilyn, even if oversized, complete with enough makeup to make a Kardashian blush.
The transformation was so convincing that for a moment I wondered if Marilyn herself had returned from the great beyond to grace us with her presence. But no, it was indeed Giuliani, and he seemed to be relishing his role. He glided around the room, bestowing air kisses and batting his false eyelashes with the finesse of a seasoned starlet.
At one point, the evening took an even more surreal turn. There, in the corner, I spotted Donald Trump, then just a businessman with a flair for the dramatic, seemingly coming on to Rudy as Marilyn. Trump, with his characteristic bravado, appeared utterly unfazed by the fact that he was flirting with the man who had once sent mobsters to prison.
Giuliani, or rather Marilyn, responded with a giggle that would have made Monroe herself proud. The duo made quite the pair, and I couldn’t help but think that if there were ever a Broadway production of Victor Victoria, they had found their leads.
Back to the present day, where we have JD Vance, who, if the rumors are to be believed, may be trying to capture a bit of that old Monroe magic himself. Is it just those piercing baby blues, or does he indeed dabble in a bit of eyeliner to give his public appearances that extra oomph?
Perhaps it’s an attempt to soften his image. After all, the author of Hillbilly Elegy is known for his gritty, unvarnished portrayal of life in Appalachia. A touch of mascara might just be his way of saying, “I’m tough, but I’m also in touch with my sensitive side.” Or maybe he’s simply ahead of the curve in male grooming trends.
One can only imagine the conversations in the Trump camp. Does Donald, with his eye for the extravagant, give Vance pointers on how to perfect his look? “J.D., darling,” he might say, “if you want to make a splash, you’ve got to commit. A little eyeliner goes a long way, but don’t be afraid to go bold. Remember, you’re not just running for office; you’re putting on a show.”
The broader question, of course, is why Trump seems to surround himself with such colorful characters. From Giuliani’s turn as Marilyn Monroe to Vance’s rumored mascara, it’s clear that Trump’s inner circle is anything but conventional.
It might be that Trump, ever the showman, understands the value of a memorable performance. He knows that in politics, as in reality TV, standing out is half the battle. And what better way to stand out than by embracing the unexpected?
Or perhaps there’s a deeper psychological explanation. Trump, a man who has spent his life in the spotlight, might be drawn to those who, like him, are unafraid to break the mold. Whether it’s Giuliani’s audacious drag performance or Vance’s flirtation with eyeliner, these individuals share Trump’s flair for the dramatic and his willingness to defy convention.
Reflecting on that night in New York, the details become hazy, as if seen through a veil of nostalgia and too many martinis. Did Giuliani, as Marilyn, really sing a song with actress Julie Andrews from her 1982 film Victor Victoria, or is my memory playing tricks on me? It’s hard to say. What I do recall is the sense of camaraderie, the laughter, and the sheer absurdity of it all.
In the end, it doesn’t really matter. What matters is the lasting impression these larger-than-life characters leave behind. Whether it’s Giuliani’s unforgettable transformation or Vance’s enigmatic eyeliner, they all contribute to the rich tapestry of modern political theater.
As we navigate the strange and wonderful world of Trump-era politics, one thing is certain: the show must go on. And with characters like Giuliani and Vance in the cast, we’re guaranteed a performance that’s anything but dull.
So here’s to all the ex-president’s men in stilettos, the unlikely heroes who remind us that in politics, as in life, it’s not just about what you do, but how fabulously you do it.
And who knows? Maybe one day, we’ll see a Broadway musical based on these real-life escapades, complete with glitter, glamour, and just a touch of eyeliner.
TONY CASTRO, the former award-winning Los Angeles columnist and author, is a writer-at-large and the national political writer for LAMonthly. org. He can be reached at tony@tonycastro.com.
