Chicago just lost one of its titans with the passing of Lois Weisberg, 90, the city's commissioner of cultural affairs for more than two decades and, for five years before that, the director of the mayor's office of special events under Harold Washington.
It was an astonishing tenure as the head of a city office, not least because Weisberg was an irrepressible force, conceiving and rolling out one idea after another.
Some were immense and are likely to outlast many future generations, like the transformation of the old Chicago Public Library into the Chicago Cultural Center and a panopoly of live music festivals downtown. (She also founded Friends of the Parks, long before she started working for the city.)
Some were endearing experiments, like a "standstill Christmas parade" featuring "edible floats made out of candy," the Chicago Ping-Pong Festival 2000, and the infamous Milly, a dance commissioned to celebrate the new millennium.
Weisberg embraced fast experimentation and fast failure long before the concept was trendy in the startup sector. A standstill Christmas parade of candy floats sounds like a fiasco in the making, and it was; but "300 painted cow statues" kind of does, too, and it was a runaway success that's inspired imitation after imitation.
Who gets Helmut Jahn and Ed Paschke to paint cows? A woman from Austin, where Weisberg grew up in the 1920s and 1930s, in the neighborhood's Jewish section. Her father, a lawyer, was politically connected, working for the city's first Jewish governor, Henry Horner, as an assistant attorney general. "Two of my young uncles were precinct captains," she wrote in Chicago in 1995, "who were so dedicated to their jobs that they spoke with Irish accents."
Growing up in a culturally homogenous neighborhood but with a view—from her father and her family—on the rest of the city, Weisberg's ambitions grew early, as she describes in the piece.
I was perhaps ten years old when I made up my mind that I would not spend my life in Austin. Five years earlier I had started traveling downtown to the Fine Arts Building, where my mother forced me to study elocution at the Barnum School of Expression and Dramatic Art. Even worse, she enrolled me in Saturday morning classes at the Art Institute, where I learned how to make stained-glass windows out of colored paper. While the lessons were probably a waste of time and money, this exposure to the larger world was not. I wanted to get out into that world, and I made a vow that I would never push a baby buggy down Madison Street and Central Avenue when I grew up.
Weisberg grew up to become … a bit of everything: she taught first grade, wrote TV scripts, formed a radio drama company, founded an early, short-lived underground weekly, worked publicity for a jazz club, made a spoken-word record, did public affairs for the Rehabilitation Institute, and did development for a law and policy center. She befriended Tony Bennett, Dizzy Gillespie, and Thelonious Monk; she counted Lenny Bruce as a house guest, even though she wasn't a fan of his act.
Weisberg's network was so legendary that Malcolm Gladwell hung a big part of his thesis in The Tipping Point—on how things happen and travel through culture by connections—on Weisberg, whom he used to embody the principle of six degrees of separation. (Gladwell ended up with Weisberg because her son, the journalist Jacob Weisberg, was responsible for so many of Gladwell's social connections.) Here, Gladwell describes the social Rube Goldberg machine she had set up to romance her second husband:
Once, in the very early nineteen-sixties, after Lois had broken up with her first husband, she went to a party for Ralph Ellison, who was then teaching at the University of Chicago. There she spotted a young lawyer from the South Side named Bernie Weisberg. Lois liked him. He didn’t notice her, though, so she decided to write a profile of him for the Hyde Park Herald. It ran with a huge headline. Bernie still didn’t call. “I had to figure out how I was going to get to meet him again, so I remembered that he was standing in line at the reception with Ralph Ellison,” Lois says. “So I called up Ralph Ellison” — whom she had never met — “and said, ‘It’s so wonderful that you are in Chicago. You really should meet some people on the North Side. Would it be O.K. if I have a party for you?’” He said yes, and Lois sent out a hundred invitations, including one to Bernie. He came. He saw Dizzy Gillespie in the kitchen and Ralph Ellison in the living room. He was impressed. He asked Lois to go with him to see Lenny Bruce. Lois was mortified; she didn’t want this nice Jewish lawyer from the South Side to know that she knew Lenny Bruce, who was, after all, a drug addict … “Finally I said to Bernie, ‘There are some things I should tell you about. Lenny Bruce is a friend of mine. He’s staying at my house. The second thing is I’m defending a murderer.’” (But that’s another story.) Lois and Bernie were married a year later.
Gladwell spins this into a fable about social graces:
This is what the power of the people who know everyone comes down to in the end. It is not — as much as we would like to believe otherwise — something rich and complex, some potent mixture of ambition and energy and smarts and vision and insecurity. It’s much simpler than that. It’s the same lesson they teach in Sunday school. Lois knows lots of people because she likes lots of people. And all those people Lois knows and likes invariably like her, too, because there is nothing more irresistible to a human being than to be unqualifiedly liked by another.
It's not not true, and it's certainly good advice. But it's a bit like saying that Tom Brady is such a great quarterback because he's such a hard worker. Throwing a party to spend time with your crush is a great idea; calling up Ralph Ellison, Dizzy Gillespie, and Lenny Bruce to come is something beyond the mastery of social circles. It's worth emulating, but not necessarily imitating. Because there aren't many people like Lois Weisberg.