“What makes a place your home? Those things that make it unique and different. People and locations. And Billy was unique. He was authentically a Yankee Doodle pigs-in-a-blanket, a Louis’ Lunch hamburger, Sally’s and Pepe’s pizza kind of guy. He lived and died his friends, his family, and his city.”
The free spirit Mayor DeStefano and more than 200 others came to celebrate at the Playwright on Friday night was Billy Silverman, marketer of downtown New Haven properties large and small and real estate agent extraordinaire, who died last week at age 61.
He’s pictured above in front of Old Ways, the leather goods and — in the argot of the era — head shop that Silverman owned on Chapel Street in the late 1960s and 1970s.
Moving from retail into commercial real estate, Silverman became, in the words of numerous interviewees, “Mr. Downtown.” He was the go-to-guy who knew every building and every tenant in the downtown that he loved and where he did major real estate deals, despite declining health due to diabetes, as recently as a few months ago.
These deals include the condominiums coming to the College Street block between George and Crown, and the sale of the former Woolworth building near Chapel and Church. Friends like Steve Miller (in the photo above with the mayor), his close friend and business colleague of many years, both as young entrepreneurs and later at Levy Miller Maretz, attributed important influence and direction in their careers to Billy Silverman’s unique mentorship. Silverman’s official professional recognitions included honors over many years from the Commercial and Industrial Division of the Greater New Haven Board of Realtors.
What made Silverman such a memorable character to so many hoisting glasses in his memory and honor including (right to left), son Jesse, daughter Rebecca, brother Henry, and ex-wife Carol Cohen)? A cluster of characteristics that seemed almost contradictory and yet which point to the mystery of being, well, human. While the mayor said, “My first impression of Billy was that he was a street person,” Silverman came to be the guy the mayor and other movers-and-shakers in government would consult about what was happening in the real estate market downtown, about what was possible, and what not.
Jesse called him, with a wink, a “character of Biblical proportion,” who needed his daily dose of human contact and wild talk the way other people need food and water. “Imagine going to a parent-teacher conference with a dad like that!”
According to his friend of 30 years, Richard Sloan, and Sloan’s son Brett (pictured here with, on the right, Steve Miller, of Levy Miller Maretz), Silverman was like a second father. “Billy carried into his adult life the spirit of the hippies,” said the older Sloan. “He was absolutely open to everything. In some sense, yes, he was like a kid, but did he ever know his business, and when he pursued something, cars, or antique toys, he learned absolutely everything about it.”
Young Sloan attributed to Silverman interest and encouragement to pursue a career in art that he at first had to keep from his parents. “Every time I hung out with Billy,” he said, “I learned something.” Silverman attended an opening of Sloan’s art work in Soho in New York and commissioned art work based on it that Sloan was not able to finish before Silverman died. “It’s a kind of miniature diorama,” as he described it, “with antique cars.”
In the real estate world, where so much paperwork indicates a trust-but-verify attitude, what set Silverman apart, said Sloan, was an absolute integrity. “He was very old school. He looked you in the eye and he shook your hand, and in that handshake everything was sealed. Whether it was a deal for a $50 toy or a $5 million dollar property, it was in the handshake. Dollar value did not matter to him. It was integrity and the art of the deal. That was absolutely unique with Billy.”
Silverman’s listen-to-your-own drummer, follow-your-own rules spirit was celebrated not only in words but also in fashion. “One of his trademarks,” said Ed Schwartz, Silverman’s colleague at Levy Miller Maretz, “was that Billy wore no socks. It didn’t matter if it was the coldest day in January. It was part of his trademark, and in his honor many of us are sockless tonight, and proud of it.
“We were a good match. I’m mellow and Billy was intense and short tempered. I mean when his cell phone rang, before he flipped it open, he would start to yell at it: ‘Who the hell are you! Screw you!’ And then he would open it and speak so politely. I mean, though, what a straight shooter he was, a person who did absolutely everything in life out of enthusiasm and love, a real mensch. And I learned a lot from him”
Such as? “He really understood people and cared about them, and they felt it. From Billy I learned how to tell people the truth without hurting them. That’s no easy thing. You know how you do it? You speak not as an expert to a novice, but more in a fatherly tone of giving advice. It’s just not the same around here. I miss him. What a treasure he was, and always will be.”
So what was it about New Haven that Billy Silverman particularly loved?
“Oh, the people,” said Jesse. “And also that a city this size, where one could know everybody, also has so much to offer.” Then, of course, everyone, like the mayor, kept mentioning eateries close to Silverman’s gastronomic heart. Add to the list Big Top up on Whalley (Sloan said Silverman pursued the perfect hot dog). Then there was Katz’s deli, where he enjoyed hanging out with the alte cockers. (Sloan said Silverman was not traditionally Jewish or religious, but very spiritual.) And then, perhaps most of all, was the picnicking on the Green, where all New Haven gathered, all people and all classes, for the summer concerts. Silverman did not miss a one of them. “We found our spot early and sat and listened,” said Sloan. “Music of the ‘50s and ‘60s he loved best of all, but anything. He was open to anything.”
Here was a man still so alive in the imagination of the crowd at Playwright, that one could picture him now, as Carol Cohen said, just about coming in right through the door. Or perhaps he was elsewhere, shaking a different kind of hand, making a different kind of deal, up on some perfectly groomed celestial green that, yes, in Billy Silverman’s mind, was very beautiful, but not quite like his beloved New Haven.