Donald Trump made his first appearance on late-night television forty years ago this month—but it wasn’t as a scheduled guest.
Instead, David Letterman was spending an afternoon sightseeing with two out-of-town tourists when their excursion took them to Trump Tower. An enterprising producer discovered that the building’s famous owner happened to be upstairs—and talked him into letting Letterman and his cameras drop by.
It would be the start of a relationship that would ultimately see Trump appear on Letterman’s shows more than 30 times.
The tourists—Louisville couple Tonya Anderson and Neil Bordy—had no idea their weekend getaway was about to take such a turn.
“I brought my then-girlfriend, now wife, to New York to celebrate her 30th birthday,” Neil tells LateNighter. It was Tonya’s first-ever visit to the city.
“I’m from a smaller town in Kentucky,” Tonya explains. “Back in those days, you were hearing a lot about gangs and murders and a lot of crime in New York City. I was convinced I’d probably see a murder on the street.”
In fact, Tonya initially concluded that someone had been killed in front of their hotel when she and Neil spotted a crowd gathering near the lobby doors. The couple avoided the throng and headed for another exit.
That’s where they ran into Letterman and his camera crew.
No producer had approached them beforehand, Neil says. “I guess Letterman was just waiting for some unassuming couple to walk out of that hotel.”
The Late Night host asked the pair if he could tag along for an afternoon of sightseeing. They agreed, despite fearing they’d become the butt of Letterman’s famously acerbic sense of humor.
“We just thought he would be mean,” says Tonya. “But he was the nicest guy in the world.”
It turned out that Neil and Dave had plenty to talk about. Both had gone to college in Indiana—Bordy at Indiana University, Letterman at Ball State—giving them some easy cab-ride conversation as Letterman joined the couple on a visit to the Empire State Building.
From there, the sightseeing continued at Trump Tower.
Letterman asked what the couple knew about Donald Trump. Tonya remembered a few things from a 1985 60 Minutes story.
“He’s shoving people out of their homes,” she told Letterman as they rode one of Trump Tower’s escalators.
Tonya tells LateNighter that Trump Tower had already been on their weekend itinerary. A social worker back in Kentucky, she wanted to see its much-publicized opulence for herself.
Letterman wasted little time having fun with that opulence. Tonya twirled in slow motion while trying on ostentatious jewelry and $10,000 furs in Trump Tower shops. Letterman, meanwhile, asked a salesman whether the foxes used to make the coats had been clubbed to death or shot in the head.
As Letterman pestered a security guard, a producer learned Trump was upstairs in his office and asked if they could drop by. Trump agreed.
“I almost never stay up late enough to watch Letterman, but I know he’s hot,” Trump recalled in his bestseller the following year, The Art of the Deal. “I say sure.”
The resulting encounter was brief—no more than 10 minutes or so, Neil remembers.
Trump kept a grin fixed on his face as Letterman searched beneath his desk for Doug Flutie, the diminutive quarterback of Trump’s USFL team, the New Jersey Generals, and asked the real-estate tycoon if he could do anything about the heat in his building.
Trump had kind words for “the very nice-looking couple from Louisville,” in his book, recalling a joke about going in with them on a Kentucky land deal.
“He was very gracious,” Tonya concedes, although she says meeting Trump did nothing to change her opinion of his real-estate practices.
Tonya didn’t get to keep the furs or jewels, and the couple wasn’t paid for spending several hours with Letterman. In lieu of a check, NBC picked up the couple’s dinner the following evening at a fancy French restaurant.
As for their 15 minutes of fame, those have proven surprisingly durable. Thanks in no small part to their role in Trump’s first-ever late-night appearance, the segment has followed them for four decades.
“People still talk about it,” Tonya says.
Not all of that newfound fame was welcome, though. The birthday getaway had been something of a secret.
“We were 30 years old, but we hadn’t told our families that we were going off together to New York,” Neil confesses.
Once local news stations began covering their upcoming appearance, keeping the trip quiet was no longer an option. They had to tell Tonya’s parents before the Late Night episode aired.
“They weren’t too thrilled about me going anywhere with a guy I wasn’t married to for a weekend,” she admits.
The two were married less in August 1987—less than a year later—and they remain together today.
Watch Tonya and Neil’s afternoon of sightseeing with Letterman—including their unexpected detour into Trump’s office—below.
