Character Sketch: The OG of the Upper West Side

by Daniel Krieger

Many years ago, at the age of 33, Robert Kalich hit a bad losing streak. He was dead broke. He was in debt $40,000 from gambling. He was stuck in a toxic marriage to a woman he couldn’t get along with but couldn’t keep his hands off of. Nothing was working out. And it was the one and only time in his entire life that he moved away from the Upper West Side to the Upper East Side, which he hated. Then his wife threw him out and he moved in with his parents on West End Avenue. Heartbroken, he decided he was going to show her he could make it.

“I was a degenerate until I was 33,” he says, matter-of-factly, during a recent interview. But 33 was a turning point. That was when he figured out how to break the losing streak thanks, Kalich says, to his burning ambition, a deep understanding of basketball and his facility with numbers.

Leaning back in a carved wooden chair in his rent-stabilized Central Park South penthouse, where he’s lived since 1972, Kalich talks openly about his charmed and exuberant life. He is now 85, with a paunch and a full head of slightly disheveled white hair. He’s wearing a Georgia Tech T-shirt, Adidas sweatpants and black sneakers. The north-facing window of his 21st-floor apartment has a sweeping view of Central Park. Each room, the kitchen included, is lined with books, about 10,000 in total, all literature, from all over the world. Most of the furniture in the densely-packed (but very orderly) four-room space is built by the master craftsman Richard Rothbard.

Blunt, brash, sarcastic, plainspoken, playful and impatient with my ignorance, Kalich sounds like an old school ‘New Yawka’ dropping his r’s and taking little time for niceties. He’s what my mother, who grew up in Queens, would’ve called, “a real charactah.”

What else is Robert Kalich? He is a novelist whose fourth novel, a fictionalized memoir called “Impossible to be Human,” comes out in October, completing his auto-fiction trilogy that concludes the story of “The Handicapper” (1981) and “David Lazar” (2019). He is also a nonfiction writer of a half dozen books. He is a professional gambler — more specifically, a “handicapper.” And it was his genius at gambling that turned things around when he hit rock bottom. By studying and analyzing college basketball in order to gain an edge, which is what a handicapper does, he cracked the code and began winning at gambling, creating a lucrative industrial-size operation, he says.

“I’ve had a big life,” he says, surveying his eight decades on earth. “And I never had a small ego. I wanted to own the city. I was as big as you get and I knew everybody.”

His friends in the 1960’s, 70’s and 80’s spanned a who’s who of luminaries in theater, film, government, sports, finance, real estate – you name it. He used to host summer parties with 150 guests on his 3,000-square-foot terrace; guests included the likes of Robert De Niro, Ed Koch, Barbra Streisand, Dick Barnett, Al Pacino, La Toya Jackson, Earl Monroe.

Kalich grew up on 106th Street and West End Avenue. His dad, Kalman Kalich, was a renowned cantor at the Ohab Zedek Synagogue on West 95th Street, but Kalich thought religion was “inane” and his dad an “ignoramus” who never got a proper education.

His mother was a professor of psychology at Barnard College, and it was she who raised Kalich and his identical twin brother, Richard, to be worldly men of letters in a household chock-full of culture. Kalich says he always wanted to be a novelist and from childhood read voraciously. “When I read Dostoyevsky,” he says, “I thought I could be Dostoyevsky.”

The Jewish enclave on the Upper West Side was a great place for a kid to grow up in the 1940s and 50s, he says, calling it “much more humane, not like today with the digital culture where you have nothing but alienation and spiritual impoverishment.”

After graduating from NYU, in 1960 he got a job at The Daily Mirror, a tabloid published by William Randolph Hearst. He started as a copy boy and moved up to obit writer. Then he covered nightlife, like Tony Curtis in the film, “The Sweet Smell of Success.” “I was Broadway Bob,” he says, “and I was getting to know the most gorgeous girls in the city. I loved that job.” But he quit shortly before the paper went under in 1963 and became a social worker in Harlem due to the demands of his first wife who wanted him to earn more money.

On two subjects, Kalich shows some modesty. The first is his twin brother, Richard, who is also a novelist and lives down the street. They talk several times a day and are, as Kalich puts it, two sides of the same coin — the same yet different. “All I can tell you about my fucking eccentric, neurotic, completely crazy brother is that there’s never a day I’m with him when I don’t learn something,” Kalich says. “He is the consummate intellectual. I’m not an intellectual like him. He is totally pure. Without any corruption. I’ve had nothing but corruption in my life since the age of 33.”

The second subject that he speaks of with modesty is his sixth wife, Brunde Broady, a philanthropist, businesswoman and writer who spends most of her time at their estate in North Salem, NY, in Westchester, where Kalich goes on weekends. They have a son, Knute, who studies at Georgia Tech.  “When I met my wife, I was ready to settle down and live a domesticated life, to a certain extent,” he says. “The best 25 years of my life have been the past 25 years with her.”

Looking back on his eventful journey through life with its ups and downs, good fortune, twists and triumphs, Kalich is quite pleased with how things turned out. Standing on his terrace under the late summer sun, surrounded by abundant lush greenery and with the sprawling expanse of Central Park in the background, he turns to me and says: “I’ve had a great life, and you know what? I’d like to do it all over again.”