Back in the summer of 1988 while Donald Trump was publicly basking in the success of his book, The Art of the Deal, he quietly came to the Vineyard with a little known blonde model, and former Resaca Beach Poster Girl from Dalton, Ga.
Back in the summer of 1988 while Donald Trump was publicly basking in the success of his book, The Art of the Deal, he quietly came to the Vineyard with a little known blonde model, and former Resaca Beach Poster Girl from Dalton, Ga., with whom he was having an extra-marital affair later dubbed “one of the biggest sex scandals of the 1990s that triggered the divorce of the century.”
At the time, rumors of his “seismic marital rift” whipped around the social circuit. An Atlantic city photographer had already threatened to release photos of Mr. Trump’s clandestine partner. Yet despite speculation in the tabloids and gossip press, the identity of the Donald’s paramour still remained a mystery.
It would be another 18 months before New York columnist Liz Smith broke the story of his season of infidelity. When Marla Maples was finally tagged as the other woman, the liaison had been four years running. The winter after her husband’s Vineyard escapade, Ivana Trump learned of the pair’s affair and confronted Marla at a ski resort in Aspen with her famous line: “You bitch. Leave my husband alone!”
Mr. Trump soon announced the end of his 12-year marriage and subsequently married Marla following the news of her pregnancy with their daughter, Tiffany.
In the past three decades, the events of Mr. Trump’s tryst with Marla have been reported ad nauseam. Curiously absent from all the coverage, however, is any mention of the fact that the Donald and Marla had a secret liaison on July 4, 1988 right in the heart of downtown Edgartown amidst the crowds gathered for the Island’s annual Independence Day parade.
Nothing unusual differentiated that Fourth of July from others. Five of us decided to go down-Island to watch the parade. Our plan was to get a good vantage point on Main street but we ended up arriving early. With time to kill, we decided to grab a snack of fried clams and oysters. While a crowd milled about, Spencer, Michael and I hung back while Meg and Ellen joined the line at the counter.
Suddenly, Meg rushed over and announced, “that’s Marla Maples” pointing at a sporty-looking blonde woman standing on line.
“Who?” we collectively asked.
“Marla Maples. She’s rumored to be having an affair with Donald Trump.”
Now this piqued our interest. Meg worked for the Rupert Murdoch company that owned the The New York Post, and was privy to speculation about Trump’s affair.
Marla then left the counter and approached the driver’s side of a dark compact car parked along North Water street. Inside sat the Donald with all the markings of a man in hiding. On a pleasant July day, the windows were shut tight. He wore an overcoat with the collar turned up James Dean style and a baseball cap slung low to mask his face. He lowered the window slightly, Marla bent down and they spoke briefly. She returned to the counter while he rolled the window up.
The three of us guys took turns walking around the car to confirm the Donald’s identity. Despite his makeshift disguise, it was clearly the Donald inside, orange hair puffing out the sides of his baseball cap and wearing an impatient scowl.
A short time later, Marla came back to the car carrying two large cups that she handed through the opened window. Moments later she returned with two plates, then got into the car.
We looked about, wondering if anyone else had recognized the budding developer and casino king from New York. But the crowd seemed unaware of its famous guest and carried on as if it were an ordinary July day in the Vineyard.
The Donald proceeded to drive slowly toward the Edgartown dock. We followed on foot, now in detective mode. We then waited 20 minutes while the Donald and Marla sat in their car eating their meal. We moved closer and took up strategic positions where we could snoop without being detected. But the parade was starting soon and we didn’t want to miss it, so we developed Plan B. If they would not leave the car, we would go to it. The scheme was for Spencer, a photographer carrying a compact size Olympus XA camera, to approach the couple and take a few photos.
“Just knock on the window as if you want to ask for directions or the time,” I suggested. “And when he opens it, pull out the camera and keep shooting.”
But Spencer took a more subtle tack. He ambled toward the car wearing an I’m-A-Lost-Tourist look with the camera curled in his palm at hip height. He circled it once, then again, before returning to report: “I think I got them through the windshield.”
Convinced that Mr. Trump would not reveal himself publicly no matter how long we staked him out, we decided to end to our Independence Day drama with the Donald and head off toward the parade. The next day Meg called to check in with her office at Murdoch Magazines and ended up relaying the story to a fellow staffer. Suddenly, our accidental sighting was stirring up quite a buzz in New York.
Photos of the Donald and Marla together could be worth up to $10,000 a piece. Did we have any more intel on where the couple was staying, how long they’d been on the Island or what they had done?
We needed to get the film, but unfortunately it had already left the Island for processing. Several agonizing days passed before we would find out if we had the money shot.
The search for Donald took on its own life at this point. It was our understanding that the Murdoch group dispatched a team of reporters to the Vineyard to hunt down the Donald and Marla and hopefully capture a cover story with the first photo of the two together. We also heard that other tabloids, which routinely monitored their competitor’s movements, sent their own crews in quest of a story. Apparently, after a day or two of scouring the Vineyard, the national media returned to the big city empty handed.
Had the Donald departed as silently as he had slipped in? Did he and Marla retreat to the Trump Princess somewhere off the coast of Menemsha? If so, the future Presidential candidate and the future No Excuses model left barely a footprint in their wake, a far cry from the dinosaur tracks he makes these days. And we were left with a tale to tell and little more.
As for Spencer’s photos, they were finally delivered just after we left the Island. His hopes for a big payout dissolved as the negatives failed to capture any incriminating moments. The Donald and Marla’s tryst remained their little secret, for at least a while longer. Secret, that is, except for a small item that ran in the New York Post a few days after the Fourth of July holiday linking Marla Maples with “one of New York’s biggest business tycoons, a married man.”
And as for us, we had the scoop but lacked the proof to close. And so it goes.

Comments
Concerned that the Vineyard
ConcernedConcerned that the Vineyard Gazette has reached a new low with this article.
Ouch! I'm surprised at the
John Rosenmiller New YorkOuch! I'm surprised at the response some readers expressed that the Gazette is flirting with tabloid journalism. I doubt this article will change the paper's dignified tone. It was meant as a tongue-in-check piece about events that did happen. Maybe if the headline had been "Headless Man in Topless Bar" with a photo of a car trunk it would have been evident. Its a story that happened nearly 30 years ago that, in light of the Republican mess that's going on now, seems pretty tame. But if it was offensive to you or others, that certainly was not the intent. It's not like it is the first fluff piece written about Obama, Clinton or the other myriad of celebrities who visit in the summers. What I find interesting, and surprising, is how many Massachusetts voters cast ballot for Trump. Maybe this is a story that deserves further exploration.
Hi, John! Great to see your
Louisa Hufstader EdgartownHi, John! Great to see your name again. We should get together and swap more sordid tales of tabloid trashiness.
Spoofing the other alleged
George Stein EdgartownSpoofing the other alleged bastion of Island media coverage apparently. Due for the gutter after all these years. At least they post reader comments of criticism. I applaud their willingness to bear comments of a nature the powers that be over there would be genuinely combative about for days. The removal of opportunity to seek higher ground with the other team is a sign they acknowledge they embarrassed themselves on a regular basis. That is not seen with this publication on any sort of basis. I can forgive those who can admit criticism is an integral part of our first amendment rights. Bravo!
That the Vineyard Gazette has
Very ConcernedThat the Vineyard Gazette has reached a new tabloid low with this article. Also very concerned that the Vineyard Gazette might now be blocking comments like this that are non threatening yet clearly truthful. Are you censoring the comments because you know that this is a tabloid article?
"But Spencer took a more
PJE Aquinnah"But Spencer took a more subtle tact." Tact had nothing to do with it, and in this case, he took a different tack.
Doesn't anyone remember the
Adelaide Kent New YorkDoesn't anyone remember the Chappaquiddick nightmare of the 60's that ended Ted Kennedy's run for the presidency? What this little article shows is how far technology has progressed since 1988!
"Ape Visits Vineyard During
Ricardo Thunder"Ape Visits Vineyard During 80's"
Great Article!
seriously?!?! Is no news
Susan M WH CTseriously?!?! Is no news media reader/viewer exempt from such
"historically relevant" moments?!?!
Yep, someone had to bring up
DONNA RUSSELL Braddock Bay, NYYep, someone had to bring up The Bridge. But thanks, John, you were holding a Trump card and you played it. Next thing you know, Marla will be mentioned in the same sentence with "Trick." Let's hope that by November, we'll all realize that he plays Below the Line in everything and has no Finesse, and we can shout a heartfelt "Bye!" as we Discard him! I'm no Dummy - count me a Strong Notrump!
Curious as to how anyone
Olga StetsonCurious as to how anyone managed to get a parking spot on the dock on the 4th of July. That was nigh impossible even in the 60's.
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