The Hill and Don Show, by Debbie Tuma

Debbie Tuma and Donald Trump on the beach in East Hampton around 2002.

With the latest email scandals and accusations of womanizing, all eyes have been on Hillary Clinton and Donald Trump. In the months leading up to the election, it has been one surprise after another, proving to be riveting and entertaining at the least. Who would have guessed, when these two candidates were high-profile presences in the Hamptons these past few decades, that they would end up competing for the highest position in the nation?

Donald Trump and his two brothers, the late Fred Trump and Robert Trump, have been out here for years. When I became a babysitter for Fred and Mary Trump at their house on Lake Montauk as a teenager in the 1960s, I never dreamed that one of Fred’s younger brothers would one day run for president. They were like any other gorgeous young couple, with two adorable kids and a dog with the funny name of Two-No-Trump, which is a poker term. 

Fred had a boat that he kept on Lake Montauk to take his family fishing. I loved to go to their modern house with its sweeping water views, where they would generously tell me to eat whatever I wanted, use the phone however much I wanted (and back then each call cost money), and even have my friends over. 

They used to go to parties until the wee hours of the night, and Fred would drive me home, throwing me $20 bills, which back then was a small fortune for babysitting and helped put me through college. I was sorry to learn years later that he had died at a young age. 

In Montauk we would also see Robert Trump, who spent time around Gurney’s Inn. He dated and eventually started living with Anne Marie Monte, the niece of Nick Monte, the inn’s former owner. I remember seeing them at New Year’s Eve, Halloween, and other special occasions at Gurney’s. The inn used to have theme parties for New Year’s Eve, and one year it was all about Woodstock, with everyone dressed as hippies, including Robert. He had a great sense of humor, parading around in a longhaired wig and wild clothes. 

I first started seeing Donald Trump in the 1990s at polo games in Bridgehampton. He would often take his daughter Ivanka and other family members, and I didn’t know if he was into horses or the game itself, but he seemed to enjoy socializing with other Hamptons celebs in the V.I.P. tent, watching the action from the sidelines. Back then I hosted a television show for WVVH-TV in East Hampton called “Innerview in the Hamptons,” produced by David Nadal of Blue Lemon TV, and we interviewed Donald at those games. 

We also ran into a tanned Donald Trump on the ocean beach, looking more casual in white shorts, white polo shirt, and white visor. He was with Marla Maples, his wife then, at a charity volleyball tournament to benefit pediatric AIDS. “I came here because we are trying to raise money and awareness of this important cause,” he said.

I asked him about his yacht, which he tried to bring into Montauk Harbor, but the draft was too deep, so he couldn’t get it to the Montauk Yacht Club. He talked about how he loved boating, fishing, and Montauk, and how he was enjoying his time in the Hamptons that summer. He was in a good mood. But when we started asking more personal questions, about his plans for the summer and rumors about his marriage having problems, he abruptly got up and walked off the set. That was the last we saw of him, but we left that segment in our show.

I also saw Hillary Clinton many times here, when she came as first lady with President Bill Clinton, later when she was raising money for her Senate race, and more recently during her presidential campaign. She and Bill flew into East Hampton Airport on several occasions to attend parties at the homes of the lobbyist Liz Robbins and the fashion designer Vera Wang, with entertainment by the comedian Jon Stewart and the rocker Jon Bon Jovi. 

I will never forget one of the biggest events they attended, a 1998 Democratic fund-raiser at the Amagansett home of Alec Baldwin and Kim Bassinger, his wife at the time. It was the height of summer, a moonlit night at their sprawling farmhouse, and hundreds of people paid $1,000 and up for tickets. They sipped wine, dined on hors d’oeuvres, and gathered to dance to Bill Clinton’s favorite band, Hootie and the Blowfish.

But security was tight, and the press was banned, so the only alternative was to sneak in under the gates and bushes. This I did, as I had to get the story, pretending to be a guest and staying in the shadows. It was a thrill to see Bill and Hillary lined up on the porch alongside Bassinger and Baldwin, who was the host and was thought to have political ambitions then. They greeted the crowd with their speeches, and I tried to take notes quickly so I could run back to the bushes and call them in to my editor in the city.

I got much closer to Hillary during her Senate campaign swing, when she spent a day touring East Hampton. This time, the press was allowed, and I followed her as she divided her time between the town’s older and younger generations. I still remember her black pantsuit and bright pink blouse as she shook hands and posed for photos at the senior citizens center. 

Hillary told the seniors she would do “everything possible” to protect Social Security, Medicare, and prescription drug programs and keep the costs down, as her own mother, in her 80s, was in a similar situation. 

She spent the rest of the day at the day care center, where she seemed to be at ease with the children and enjoyed their questions. She asked if anyone knew who the president was, or her cat’s name, or her dog’s name. The kids weren’t so sure of the president, but they knew Socks the cat and Buddy the dog. They asked her if the animals were real, and she answered, “Yes, they’re real, and they live with us in the White House.” 

As she talked with the children, Hillary loosened up and seemed to lose herself in their innocent humor. As she sat on a tiny chair in the middle of the 4-year-olds, they handed her bunches of flowers. 

“Did you pick these for me?” she wanted to know. 

“No, I got them in the flower store,” one boy piped up. “Some of them smell.”

Hillary later burst out laughing when she read a story to the kids about a caterpillar that couldn’t stop eating everything in sight. She told them how caterpillars turn into butterflies, asking if they’d ever seen a butterfly.

A couple of years ago, as secretary of state, Clinton was again sitting with a book before a crowd in East Hampton, but this time it was her own book, “Hard Choices,” which she launched with a signing at BookHampton. I couldn’t believe the line waiting for hours to meet her and have her sign copies — it went from one end of Main Street to the other, and included people protesting problems in the Middle East. 

No matter who wins this Election Day, it has been exciting to see these two candidates in the Hamptons. It seems as though, sooner or later, everyone comes here. We may not be in the pulse of Washington, D.C., but living in a popular summer resort we’ve had the privilege of seeing the rise of these two candidates in a more relaxed, casual, and fun environment — right in our own backyard.

Debbie Tuma is a freelance writer and a host at WLNG Radio. She lives in Riverhead and can be reached at