Just after evening came to the city last Friday, Richard Lipsky appeared in the lobby of the Normandy on Riverside Drive. Gone was the Bluetooth headset that seemed welded to his ear as he conducted his business in the lobby of City Hall or the State Capitol. Gone, too, was the thick red leather-bound restaurant-reservation-style book that Mr. Lipsky used to keep appointments for the one-man lobbying shop that battered and bent governors, mayors and lawmakers on both sides of the aisle.
Instead of one of his famously dark suits, Mr. Lipsky was wearing a gray tracksuit with red stripes and sneakers; a gold chain peeked out at the neckline of a white undershirt. The bags under his eyes were larger than usual, and the eyes themselves stained a kind of bright red. He put his hand on The Observer's shoulder and guided us out into the still-gathering darkness of 86th Street, past the earshot of the doormen watching over one of the city's premier Art Deco addresses, where he owns a $1.6 million apartment.
The day before, Mr. Lipsky had surrendered to federal prosecutors who accused him of using his clients' money to buy off Carl Kruger, a powerful state senator from Brooklyn. Investigators found more than $100,000 in Mr. Lipsky's home safe and more than $4,000 in cash stuffed in a suit pocket.
His lawyer instructed him to not to talk to the press, but he advised us to read some of the clippings about him and to talk to his clients.
"I like to fight for the underdog," he said, before disappearing back inside. "That's just who I am."
In the hours following Mr. Lipsky's indictment, the press portrayed him as a powerhouse lobbyist who had met a sudden and surprising end only when it was discovered that he was lining the pockets of a legislator to help "the little guys"-the mostly minority small-business owners that he represented.
The truth is more complicated. Mr. Lipsky, the son of a theatrical press agent who holds a Ph.D. in political science, struck many as a strange figure around City Hall. He eschewed the shmoozing, backslapping manner of most lobbyists. People who have known him for decades can't ever recall him mentioning anything about his family or his home. He had no assistant, no fancy conference room, preferring instead to communicate via cell phone and over email and meet wherever his clients or lawmakers were. He bragged about his relationship to Mr. Kruger and his allies in the Senate, known as the Four Amigos, even though they shut down state government for a month in 2009, and now a majority of that little group are ensnared in serious ethical violations.
"I don't think you will talk to anybody around here who will tell you they are very surprised about this," one council member said. "He just had a certain way about him, the way he spoke, the way he talked to people, that was just sort of weasely. He became much more aggressive and pushy as the years went on."
Lobbying is by its a nature a sordid affair, but Mr. Lipsky always seemed to hold himself to a higher standard. The term "messianic" came up more than a few times by those who have worked with him, and his colleagues noted his willingness to skewer opponents.
But over the past several years, Mr. Lipsky kept up the harsh denunciations of deep-pocketed city players while simultaneously courting them. The self-styled David parlayed his small-business community contacts to help Forest City Ratner develop Atlantic Yards, and paved the way for Target's expansion into East Harlem. And, more recently, Mr. Lipsky approached the Committee to Save New York, the coalition of monied business groups behind Governor Andrew Cuomo's efforts to curb spending and lower taxes, selling himself as the defender of the little guy who would bring them credibility with the larger public.
"He changed from someone who was very much a champion of the underdog to become much more of a mercenary who needed constant self-promotion," said one colleague.
Mr. Lipsky always had a knack for getting into the newspapers, mainly for his willingness to resort to bombast and hyperbole, and when that failed, he took to his blog, Mom and Pop NYC, which he updated and emailed out to reporters several times a day. There, he compared one lawmaker to a Nazi; accused the city's Department of Health of "maniacal overreach" for starting an ad campaign that warned of the dangers of excessive drinking; and said Mayor Bloomberg was exploiting 9/11 families in his defense of the ground zero mosque. Unlike most consultants, who would advise their clients on what to say, Mr. Lipsky always seemed to make sure that he got his own name in the newspapers, often followed by one of his own typically bombastic quotes. In time, it seemed he was grinding his own axes instead of working for his clients. He was removed, for example, by a coalition of groups looking to fight the mayor's congestion pricing plan when he was unable to keep from making scorched-earth comments about Mr. Bloomberg's and the plan's supporters.
"It is not necessary to go out and give your opponents a leg up by engaging in personal and ad hominem attacks," said Walter McCaffrey, a fellow lobbyist who helped form the group. "Unfortunately he ended up not following that a couple of times."
Although Mr. Lipsky fashioned himself as a dragon slayer, he lost most of his crusades-Willets Point, green carts, the rezoning of Flushing, the Columbia expansion-and political insiders began to see him as little more than a parody of himself.
"In the city, he had kind of become irrelevant," said one administration official. "He made a lot of noise, but he was largely someone to be ignored. You just had to give the people he was lobbying ammunition to deal with attacks, and then he would go so over the top with his blog statements and his statements in the press that it was hard for people to take him seriously."
Over time, Mr. Lipsky had so alienated City Council Speaker Christine Quinn with his bombast that City Hall insiders say he was eventually forced to go around her and lobby individual members to press his bills, which of course infuriated the speaker's office and further marginalized Mr. Lipsky.
"He was so unabashedly anti-Bloomberg and anti-Quinn, I can't imagine anybody thought he would ever get anything done," said one.
In 2008, Mr. Lipsky was one of a few lobbyists to oppose the Council's efforts to extend term limits, a sign, politicos say, of how much his influence had waned.
Unlike Mr. Lipsky, most lobbyists wanted those in office to stay-they relied on these relationships for business. He had burned so many bridges that he needed a whole new crop of lawmakers. It makes sense, then, they say, that Mr. Lipsky would be caught handing cash over to a longtime outer-borough lawmaker. It was the only way he could get anyone to take his calls.
"He wanted to start representing the fat cats, but because he was so obnoxious and aggressive, he didn't have that many successes," said longtime lobbyist Norman Adler. "When you are under pressure like that, you pull out all the stops."