Opinion: Icarus 2.0: Did Kimberly Guilfoyle Fly Too Close to the Son?
Greece is the birthplace of “democratic values,” Kimberly Guilfoyle pointed out on Instagram after being nominated as ambassador by president-elect Donald Trump. Greece is also the birthplace of drama, which makes it a perfect fit for the two-time divorcee and dumped fiancée of Donald Trump, Jr. Subject to senate approval, this appointment could be seen as either a consolation prize…or a banishment from Mount Olympus.
Once a member of the high-flying Trump inner circle, Guilfoyle has tumbled to earth like Icarus. Guilfoyle, 55, and Trump Jr., 46, went public with their romance in 2018—the same year he divorced his then-wife Vanessa with whom he shares five children.
Together, the shiny-new MAGA power couple purchased a 7-bedroom, 12-bathroom home in Jupiter, Florida for $9.7 million. Presumably, Guilfoyle is rattling around that home, using a different bathroom for every pee while Trump Jr. vacations in Italy with new girlfriend Bettina Anderson who was born around the time that Guilfoyle headed to college.
These plot twists could make Guilfoyle laugh or cry, which brings us back to Greek drama. As early as 600 B.C., the Greeks divided drama into comedy and tragedy. Tragedy focused on lost love, hubris, and revenge while comedy tackled vanity, foolishness, and fart jokes. Both apply to Guilfoyle’s current situation.
This duality has stalked Guilfoyle for years, illustrated by two persistent images of the disgraced former Fox News host. The first is a behind-the-scenes clip of Guilfoyle at the ellipse on January 6, 2021. Along with then-President Trump and daughter Ivanka, Kimberly waits for the event to begin as the 1980s platinum hit Laura song “Gloria” pulsates in the VIP tent. Trump Jr. records the historical moment, zeroing his phone lens on Guilfoyle who’s wearing a kicky cape and a pound of makeup. She appears to be in high spirits (perhaps because she was about to pocket $60,000 for a two-minute speech) so when her then-boyfriend calls out to her, she shimmies for the camera. In that brief clip, Guilfoyle comes across as plucky and sexy.
Guilfoyle’s other unforgettable image is more ominous. At the 2020 Republican National Convention amid the pandemic, Guilfoyle takes the podium and awkwardly attempts to fill the void with her larger-than-life personality. She speaks too quickly and too loudly, before throwing her arms out at the end and proclaiming,
“The best…
is yet…
to come!”
In this brief clip, Guilfoyle appears to be taunting the gods with hubris. So let’s try on both dramatic masks and try to predict two possible outcomes for Guilfoyle as she heads to Greece.
Comedy Mask
Guilfoyle could well be heading into her own romcom—think My Big Fat Greek Wedding meets Eat. Pray. Love. Although in this case, the eating might be suppressed by semaglutides, the praying is definitely Christian, and the love is transactional. In this scenario, the former First Lady of San Francisco would be following in the footsteps of former First Lady of the United States Jacqueline Kennedy who recuperated from the loss of her assassinated husband (tragedy!) by marrying froggy Greek shipping magnate Aristotle Onassis (comedy!)
A Greek billionaire with a yacht would suit the gal in the kicky cape. Or perhaps Guilfoyle will set her sights on royalty. Sadly, Prince Constantine Alexios of Greece dropped out of the market in June when he married American model Brooks Nader. Still, Guilfoyle can always catch someone on the rebound. Shipbuilder extraordinaire George Economou is currently divorced and might be intrigued by someone who has juicy stories about America’s reigning family.
Or maybe Guilfoyle has banked enough of her own money to throw in with a dock worker who smells like fish but looks like Adonis. Spending days in the US Embassy and nights on the beach could lead to Guilfoyle finding an inner peace that she never knew before Dimitrios.
Tragedy Mask
Remember Medea? In Euripides’ story of betrayal, Medea helps Jason find the golden fleece before he follows the wishes of his father King Aeson and dumps Medea for a princess. Enraged, Medea poisons a bunch of people, including her own sons with Jason because that’ll show him! Somehow Medea survives, escaping via divine chariot to Athens, which is also the location of the current US embassy.
Guilfoyle could also follow in the footsteps of Medusa, a priestess who was known for her raven hair until she angered Athena who turned those locks into snakes. (Talk about extensions.) From then on, men who looked at Medusa turned into stone.
It’s hard to say whether the fates been kind or cruel to Guilfoyle. She might be Icarus, crashing into the ocean. Or she might follow another Greek myth and bounce back from being burned by Trump Jr. like a cackling phoenix rising from the ashes.
Trump Jr. has repeatedly praised Guilfoyle since moving on to Anderson and insists that he and his ex will always care for each other. This deep loyalty could stem from “a special bond,” as Trump Jr. put it, or perhaps a “non-disparage clause” that was added to an NDA agreement that was negotiated prior to the breakup. (Guilfoyle is a lawyer, after all.)
Guilfoyle re-invented herself after divorcing liberal darling Gavin Newsom, Governor of California and, it’s easy to imagine the soon-to-be Madame Ambassador doing so again. Will her Greek odyssey be consumed with new-found love or ancient revenge? Will she become a raven-haired Greek princess or a snake-y-haired gorgon?
At this point, only the Fates know whether the best is really yet to come.
