Donald Trump’s Hat

Beginning on page 52 of Harry Hurt III’s Lost Tycoon we are told of an “afternoon in late October” of 1989 when Donald Trump (of whom you may have heard) was taken via limousine to 45 East Eighty-fifth Street in New York City [1], then “the address of the Reed Center for plastic surgery”, to meet with a Dr. Steven Hoefflin [2] who was to perform a pair of cosmetic surgeries on him – “liposuction” around his “waist and chin” and a “scalp reduction operation” – according to an account given by Trump’s ex-wife, Ivana, under oath.

Hurt describes the procedures in detail, replete with evocations of “cannula […] hooked up to a high-suction vacuum pump” removing “about three pounds” of fat in a process “similar to coring Swiss cheese” and “slic[ing] out a part of the bald spot” like a “modern medical version of head shrinking”. During his recovery, Trump was to feel “a combination of numbness and hypersensitivity, soreness and lumpiness”.

Of the scalp reduction operation, we are told that typically “the identical procedure will be performed at least one or two more times until all or most of the bald spot disappears.” In an attempt to alleviate this need, the Dr. is said to have performed “medical-grade tattooing” which would have the skin of the bald spot match the shade of the patient’s hair.

As he convalesced in the days after the procedures, Trump “suffer[ed] nagging headaches caused by the shrinking of the scalp, the stretching of the skin, and the pain of the initial incision.” He was also upset the color of the tattooed skin did not “match the color of his hair”. And as many in their own pain are wont to do, Trump sought to externalize his pain to others.

He first called up the Dr. and said “I’m going to kill you! I’m going to sue you. I’m going to cost you so much money, I’m going to destroy your practice.”

He then sought out his then-wife, Ivana, who was “relaxing in the master bedroom of the Trump Tower triplex”. According to Ivana, under oath, Trump “storm[ed] into the room”, said “Your fucking doctor has ruined me”, flung Ivana “down onto the bed”, “pin[ned] back her arms and grab[bed] her by the hair.” According to Ivana, under oath, where he grabs her “corresponds to the spot on his head where the scalp reduction operation” was done. He “ripp[ed] out Ivana’s hair by the handful”.

Ivana “cr[ied] and scream[ed]”. Trump “rip[ped] off her clothes and unzip[ped] his pants. Then he jam[med] his penis inside her for the first time in more than sixteen months.” [3]

Eventually, Ivana was able to “run[] upstairs to her mother’s room” and “lock[] the door”. She spent the rest of that night crying there.

The next morning, Ivana returned to the master bedroom and found Trump waiting for her, her “ripped-out hair [still] scattered all over the bed” they shared. With “menacing casualness” he asked her, “Does it hurt?”

This is not the first time this story has been re-reported with, for example, coverage by The New YorkerDocumenting Trump’s Abuse of Women“, New York Magazine publishing the account months before the 2016 primaries, and Wikipedia having a page dedicated to “Donald Trump sexual misconduct allegations“, among others.

What I haven’t seen reported in conjunction with this tale is the significance of Donald Trump’s hat.

As of this writing, if one searches for “Donald Trump” at Getty Images, one has the option to peruse about half a million individual photos of approximately 14,000 events with said man. He is nothing if not well documented.

If one sorts those pictures to see the newest first, one comes across a plethora of (now stereotypical) “Make America Great Again” red hats being worn by him, worn by his supporters, sitting atop a Christmas tree, being given to a crowd, etc.

However, if one sorts those photographs beginning with the oldest, a curious result emerges. In the first four decades of his life, Trump was not photographed wearing a hat. The first time the man felt dapper enough to don one in public?

October 19, 1989.

In four photos captured by Ron Galella during a Superboat Race in Atlantic City, New Jersey, Trump can be seen wearing a white fedora and accompanied by bodyguards.

ATLANTIC CITY, NJ - OCTOBER 19: Donald Trump attends Superboat Race on October 19, 1989 at Trump Plaza Hotel in Atlantic City, New Jersey. (Photo by Ron Galella/Ron Galella Collection via Getty Images)

Donald Trump during Superboat Race - October 19, 1989 at Trump Plaza in Atlantic City, New Jersey, United States. (Photo by Ron Galella/Ron Galella Collection via Getty Images)

ATLANTIC CITY, NJ - OCTOBER 19: Donald Trump attends Superboat Race on October 19, 1989 at the Trump Plaza Hotel and Casino in Atlantic City, New Jersey. (Photo by Ron Galella/Ron Galella Collection via Getty Images)

ATLANTIC CITY, NJ - OCTOBER 19: Donald Trump attends Superboat Race on October 19, 1989 at Trump Plaza Hotel in Atlantic City, New Jersey. (Photo by Ron Galella/Ron Galella Collection via Getty Images)

Perhaps he dug the look. Maybe he thought the hat balanced out the bright pink v-neck sweater over his light pink dress shirt. Possibly he wanted to keep the sun out of his eyes.

Though, conceivably, it could have been for a different reason entirely.

The next two times there is record of Trump wearing a hat incongruous with his then-style [4] were in September of 1991 and September of 1992. (The reader is invited to recall that scalp reduction procedures typically “will be performed at least one or two more times until all or most of the bald spot disappears.”) He would not be pictured wearing another hat for another four years (this time at beach volleyball). Then another six years after that (this time at a “Celebrity Carnival to Benefit the Pediatric AIDS Foundation” with his mistress-turned-girlfriend, Melania Knauss, at the time). It was around this time that he wore his first “red hat”, though it would take over a decade for it to transform into the political symbol it has become today.

Make of this what you will.

To me, it’s quite something that a woman testified under oath about how a trip to a plastic surgeon on or around October of 1989 for a scalp reduction procedure left her husband feeling “ruined” and led to “marital relations in which he behaved very differently toward me than he had during our marriage” and that same aforementioned husband was photographed on October 19, 1989 [5] wearing a hat.

I leave to the semioticians to discern whether the meaning of Donald Trump’s hat has substantially changed from its earliest appearance to its latest and finally, eventually, to its last.


  1. Trump reportedly entered through “the service entrance” on Park Avenue.

  2. Though primarily a physician practicing in California, Dr. Hoefflin’s medical license number in the state of New York as of 1989 was 178569.

  3. In a “STATEMENT OF IVANA TRUMP” provided by Trump’s lawyer’s days before the first printing of Lost Tycoon was to be shipped out for sale, Ivana states “As a woman, I felt violated, as the love and tenderness which he normally exhibited toward me, was absent.”

  4. Though it should be noted that Trump did suit up as a Yankee in June of 1992, but this is less disjoint than the times mentioned above as he was hosting “Donald Trump’s NY vs Hollywood All-Star Game” alongside his mistress-turned-wife, Marla Maples, at the time.

  5. 55 days before 2023 Time Person of the Year Tay Sway was born.