The Upper West Side’s special election on Feb. 28 to fill an empty seat in the State Assembly has been criticized as a vestige of old Tammany-style politics, in which the Democratic machine hand-picks the winner long before the first ballot is cast.
But the Democratic Party wasn’t the only network of power brokers exerting its influence in the weeks leading up to the election.
While Manhattan Borough President Scott Stringer, U.S. Representative Jerrold L. Nadler and the other powerful cogs of the machine threw their weight behind Linda Rosenthal, an old party loyalist, cultural bigwigs and assorted Upper West Side sophisticates campaigned behind the scenes and in private soirées for one of their own: Charles Simon, a political newcomer who also happens to be Tom Brokaw’s son-in-law.
“The arts (including our beloved New York City Ballet) and the West Side are synonymous; Charles is deeply committed to preserving and nurturing both,” ballet power couple Heather Watts and Damian Woetzel wrote to friends in an e-mail. They also promised Mr. Simon that they would get fellow dancers up early and to the voting booths before leaving for a performance in Washington.
“He’s the kind of nice young man whom it seems you would want to encourage to be in politics,” said writer David Halberstam, who also sent e-mails in support of Mr. Simon, who grew up in his building. “He’s done the right kind of networking over a period of time.”
Another former neighbor, Peter Yarrow of Peter, Paul and Mary, sang a variation of “Puff the Magic Dragon” in a recorded campaign telephone message. The well-connected lawyers who play hockey with him at Chelsea Piers (their team is called Blind Justice and they hardly ever win) helped raise money and spread the word.
Mr. Brokaw, while making a point to stay out of the campaigning and fund-raising aspects of the race because he feared it would be “radioactive in some fashion,” said that he had given his son-in-law some pointers.
“When he first got started, he asked me to look at a speech, and I said, ‘Charles, don’t give this speech. Talk from the heart, and less is more. You’re introducing yourself—put the paper down and just let them know who you really are,’” Mr. Brokaw said. “That’s the type of help I gave him. It was tone and mechanics.”
Of his supporters, Mr. Simon said he considered them “incredibly important.”
“Especially on the Upper West Side, people know who they are,” he said. “Whether it is authors or journalists or musicians or all kinds of independent thinkers, this stuff kind of resonates in a way that it might not, quite frankly, in other parts of the city.”
On the afternoon of Feb. 24, Mr. Simon, a tall, slim and soft-spoken man rarely seen without a necktie, sat across the street from Zabar’s in his storefront campaign headquarters. Amid pamphlets and volunteers, the 40-year-old attorney, who worked for Janet Reno in Washington and Mary Jo White, the former U.S. Attorney for the Southern District, in New York, spoke about issues like affordable housing and education with the earnest charm of federal prosecutor Patrick Fitzgerald.
His relatively deep coffers of about $200,000 have allowed him to send out more than 100,000 pieces of mail—a high total for an obscure special election. And his connections have given him visibility and credibility among the area’s uniquely urbane voters. If nothing else, he has forced Ms. Rosenthal and Manhattan’s increasingly muscular Democratic Party to actually hit the streets and campaign in an election that most political experts agree should be a cakewalk.
“In a word, he is pesky,” said Steven M. Cohen, a Blind Justice teammate of Mr. Simon and an attorney at Kronish, Lieb, Weiner & Hellman. On the ice, Mr. Simon apparently makes up in heart what he is lacking in talent. “There was a close game where we were stunned and delighted to see Charles get a penalty for roughing. It was so out of character,” Mr. Cohen said.
Indeed, Mr. Simon doesn’t seem like the obvious choice to rage against the machine. He dresses in sober gray suits, keeps his thinning blond hair kempt and is assiduously polite. Compared to other candidates who favor zinging crowd pleasers, he tends toward longwinded thoroughness.
Yet in various debates and campaign appearances at retirement homes and civic centers in the Upper West Side, he has been the most vocal critic of the opaque political process by which the party selects candidates in special elections.
“I also believe in the democratic process. I believe in open government. I believe in transparency. I believe in accountability. I believe that we must empower voters. Too often, citizens don’t feel like citizens at all. They feel shut out and shortchanged,” Mr. Simon said at a county-committee convention on a rainy Sunday afternoon in an auditorium at the John Jay College of Criminal Justice. “I’m afraid that’s what they’re going to think about us in this room.”
Yet even as he spoke, Mr. Stringer and Mr. Nadler were on hand to remind their supporters to vote for Ms. Rosenthal, which they did, all but guaranteeing her election.
The process has been an insider’s game for years. In 1992, the party handed Mr. Stringer the Assembly job after Mr. Nadler left Albany to take a seat in Congress. Essentially, the county committee had hoped to replicate that process by choosing Ms. Rosenthal and thus ensuring her election.
“I’ve heard complaints,” said Ms. Rosenthal. “It’s something I will think about when this is all over.”
“Given the state legislation, this is the most democratic process you can have,” added Mr. Nadler, referring to the means of filling vacancies outlined in state election law. “We can say what we want, but if we pick a bad candidate, they’re going to question your judgment and ask, ‘Why should I listen to Jerry again?’”
But Mr. Simon, encouraged by his cadre of supporters, collected enough petition signatures to get on a primary ballot, which is not the outcome that the party’s leadership wanted. During a recent debate, he complained that the United Federation of Teachers had endorsed Ms. Rosenthal without bothering to interview him. That prompted jeers from Mr. Stringer’s brother, David, a local political activist who was in the audience.
“I took offense and approached him afterward and told him that I didn’t appreciate being interrupted,” said Mr. Simon politely. Witnesses say they practically scowled at one another.
But last week, Mr. Stringer and his brother looked on approvingly as Ms. Rosenthal read off an impressive list of endorsements and criticized Mr. Simon for spending so much money on his campaign.
“I don’t have Scott Stringer and Jerry Nadler and Chuck Schumer and Hillary Clinton and U.F.T. and everybody else getting my message out for me,” Mr. Simon responded.
Mr. Stringer shrugged off Mr. Simon’s criticisms.
“Believe me, this is not some preordained decision in the backroom,” said Mr. Stringer, who somewhat facetiously characterized Manhattan’s political organization as little more than “organized chaos.” He said that he was aware of Mr. Simon’s support in high-altitude circles, but argued that his candidate had the more compelling story.
“He has a right to that kind of backing,” he said. “Linda’s story is a middle-class kid—lifelong West Sider—who chose to go into public service and who worked for Jerry Nadler.”
Mr. Simon’s path is admittedly rather different.
His mother founded Landmark West, a community group dedicated to historic architecture on the Upper West Side, while his father was a senior partner in a New York law firm. He went to the Dalton School, where he was student-body president, and attended Yale University.
After graduation in 1988, he said, he drove straight to Boston to work on Michael Dukakis’ Presidential campaign, eventually doing fieldwork in Flint, Mich. After the Dukakis drubbing, he licked his wounds in Japan, where he taught English, and then attended law school at the University of Chicago. In 1992, he worked on another Presidential campaign, this time a successful one—Bill Clinton’s.
After several years working at a private law firm, he called on his contacts from the Clinton campaign and eventually landed a job as deputy associate attorney general to Ms. Reno, who came to New York to help him campaign in December.
“She was walking around in her Florida shoes with my galoshes over them,” he said. “It was hilarious.”
After working to implement the Brady Bill, which required a five-day waiting period and criminal-background check on firearms purchases from federally licensed gun dealers, Mr. Simon came back to New York to work for Ms. White. He left there to work as deputy director of criminal justice in Albany, splitting his time between the state capital and the city. In 2004, he married Mr. Brokaw’s daughter, Andrea. He said he consulted his father-in-law about his ambitions.
“I think he is already a rising star in the party and that he is going to be around,” said Ms. White, who acknowledged that the Brokaw connection certainly didn’t hurt him. “People could see his sincerity; it’s heart-warming to see. But he is also extremely effective and tenacious.”
That combination was on display last week, as Mr. Simon knocked on doors at the Amsterdam Houses projects crammed between Lincoln Center and the luxury condos where his supporters live.
But a generous dose of naïveté was also visible as he expressed surprise that Democratic Party workers had already papered the halls with Rosenthal pamphlets. He showed even more chagrin when a tenant told him that Ms. Rosenthal had been campaigning at a community center where he had been barred from entering.
“You should have went there; there was a lot of people,” the tenant said.
“That really annoys me,” said Mr. Simon, more flummoxed than furious.
He said that he had quit his job in Albany in a “leap of faith” and, in an act of supplication to the machine he is now challenging, he volunteered for Mr. Stringer’s campaign for borough president last year in the hopes of winning his support. He argues that he never expected Mr. Stinger’s endorsement, but remembers Mr. Stringer telling him that he was “not looking to play kingmaker.”
“Well,” he said, “that sort of changed a little bit.”
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