My Father and the Trumps

A strange blast from the past

This week, at the National Prayer Breakfast, Donald Trump uttered a name most New Yorkers don’t remember at all. It was a curious aside, a rare paean to bipartisanship from a president who has been, throughout his time in the White House, a scorched-Earth operator. “Democrats are gonna be able to have lunch again and dinner again with Republicans,” Trump said, apropos of not much. “Growing up, I’d see, you know, I revered senators and congressmen … they were out to dinner all the time. We had an old congressman, maybe some of—Sy Halpern from Queens, and he was a friend of my father.”

I might be the only person under the age of forty in America who knows who Sy—or Seymour—Halpern was. This is because, in the 1960s, he was my father’s boss, when my father was fresh out of college and trying to make his way in liberal Republican circles. He worked for Halpern for several strange and invigorating years, and brought to me, decades later, a trove of stories from that time. Halpern was, in fact, quite close to Fred Trump, Donald’s father. I know this because my father talked about it often. He was certain, at some point, he had caught glimpses of Fred’s irascible teenage son. Halpern’s congressional district, which no longer exists, encompassed a leafy stretch of eastern Queens that included Jamaica Estates, where Fred had his home and Donald grew up. For me, it was quite surreal to hear Donald Trump speak Halpern’s name out loud. My father, who passed away in 2023, would have been quite amused.

Halpern was a New York character. He lived, as far as my father understood, in a penthouse apartment gifted to him by Fred Trump. Fred, as a powerful New York real estate developer, was well-wired with local Democrats and Republicans alike, and took special care to cultivate Halpern, who spent fourteen years in Congress. Halpern was a species of Republican that no longer exists. He co-sponsored the Civil Rights Act of 1964 and the original Medicare legislation in 1965; along with Nelson Rockefeller and the young John Lindsay, he was a leader of the GOP’s liberal northeastern wing, and he enjoyed quite a bit of influence. My father, who was quite liberal himself, told me once he decided to get involved with the Republicans in that era because a friend had informed him, quite simply, “the line was shorter.” Then, like now, there were more Democrats in New York, and if you were young and ambitious, you didn’t have to wait as long for choice employment. And Republicans controlled plenty. Rockefeller was the governor and Lindsay was the mayor. My father’s timing was good.

Halpern had several quirks. He dressed very well and expensively. He was an adept artist who loved to sketch caricatures, and he maintained a large autograph collection. What he liked to do was sketch a caricature of someone famous, mail it to them, and have them sign it. This usually worked. I recall my father telling me Halpern, who was Jewish, had even tried to secure Hitler’s autograph. (Did it work? I don’t know.) Besides the arts, Halpern enjoyed living beyond his means. He was, at one time, more than $100,000 in debt, which included a $40,000 unsecured loan at a highly favorable interest rate from a bank that had lobbied hard in opposition to a measure Halpern had opposed on the House Banking Committee. This didn’t hurt his re-election prospects, though. He was known for his strong constituent services, and he was well-liked across the district. In those days, campaign finance rules were virtually nonexistent, and aides like my father went around to fundraisers to secure literal wads of cash.

One oddity—among many—of Donald Trump as president is that he is a living link to a mostly vanished era of New York City history. If you listen to his rallies and speeches enough, you will hear him blurt out forgotten local trivia that befuddles his fans. When he was in the Bronx, he could not shut up about renovating Wollman Rink, and I quietly enjoyed how he forced so much of the frothing MAGA fan base to hear stories about Ed Koch and the cement needed for the rink. For anyone who grew up in New York, the name Trump has been a part of the psychic architecture since birth. My father, through Halpern, would encounter Fred, and I long knew how he loomed over both Queens and Brooklyn, where Trump Village stands today—a massive Coney Island housing complex named for the father, not the son. In my novel, Glass Century, I intentionally inserted a fictional scene in which a character meets both Donald and Fred in the 1970s, under circumstances that could have been real. Even now, in Florida exile, Donald Trump is thoroughly of New York.

Halpern’s time in office would end during redistricting, which, after the 1960s, began to kill off quite a few political careers in New York. Since the House, for more than a century, has had 435 members and they are distributed based on population, New York has been bleeding away members of Congress for many decades. Every ten years, especially as the South and West have boomed, New York has lost congressional seats. Halpern, in 1972, saw his eastern Queens seat combined with Lester Wolff’s in Nassau County. Rather than run against Wolff, a Democrat, Halpern quit while he was ahead. He wanted to go out a winner. He would go on to enjoy a long life after politics, working in public relations and dying, at the age of eighty-three, in 1997. By then, Fred was nearly dead, and Donald was musing about running for president someday. I don’t think Halpern would have believed where Fred’s kid ended up.