Rudy’s Last Man Leaves City Hall, Riles Republicans

Mayor Michael Bloomberg climbed into his black sport utility vehicle one Sunday in October smarting from a sartorial gaffe: The Yankees were battling the Red Sox, and he’d been caught wearing red socks.

Inside the car, Mr. Bloomberg turned to one of his top aides, Vincent La Padula. “What color socks do you have?” he asked.

“I said, ‘They match my pants. They’re tan,'” Mr. La Padula recalled.

Mr. Bloomberg didn’t hesitate. “Fork them over,” he said.

So Mr. La Padula went sockless for the day’s next event, a parade. The incident inspired him to reflect on his niche in the Bloomberg administration.

“You do what you can,” he said in a recent interview in a corner of the empty City Council chamber. “I’m the sock guy.”

Formally, Mr. La Padula serves as the Mayor’s senior adviser, a $162,800-a-year job, but he plays the roles of super advance-man and liaison to the Mayor’s white-ethnic base. He will remain an anomaly in City Hall until he departs at the end of this year for J.P. Morgan Chase. The cowlicked 32-year-old is a Staten Islander in an administration with a distinctly Manhattan flavor. He’s a rare Republican on a Mayoral staff dominated by Democratic veterans. And he’s one of the last holdovers from the Giuliani administration.

Mr. La Padula is a tough-talking loyalist, a skill that came in handy during the Giuliani years. In an interview with The Observer, he took a few shots at Mr. Bloomberg’s would-be rivals in the 2005 Mayoral election. He called former Bronx Borough President Fernando Ferrer a “three-time loser.” He said voters will dismiss Council Speaker Gifford Miller as a young candidate who “doesn’t have the gravitas” Mayors need. And he insisted that he-never mind the incumbent Mayor-could beat Brooklyn Representative Anthony Weiner, another young man in a hurry.

The most worrying potential challenger, Mr. La Padula said, would be City Comptroller William Thompson, a veteran Brooklyn politician with a mild demeanor and a light political touch.

“He’s a serious contender,” Mr. La Padula said. “I think we’ll beat him, but he’s a serious contender.”

If Mr. Bloomberg is to win re-election, Mr. La Padula continued, “you keep crime coming down. You really improve the schools and show significant change. And I think [Mr. Bloomberg] will do that. You bring welfare numbers down. You make sure that the quality-of-life stuff does not slip at all. And that includes noise. That includes graffiti. It includes illegal dumpers. It includes making sure the homeless have a warm place to sleep, but also that they’re not on 57th and Park, or in Bayside.

“He just has to keep doing what he’s doing.”

Mr. La Padula showed little of this confidence when he was invited to join Mr. Bloomberg’s team in March of 2001. Asked by political consultant David Garth to meet the then little-known candidate, Mr. La Padula first cleared the meeting with Mr. Giuliani. “He’s a billionaire. Why don’t you sit with him?” Mr. Giuliani said. So Mr. La Padula headed up to the Park Avenue headquarters of Bloomberg L.P., where Mr. Bloomberg and Patty Harris, an aide who would become a deputy mayor, were waiting for him.

“He said, ‘Well, do you think I could win?'” Mr. La Padula recalled. “And I said, ‘I don’t think so and here’s why.'” Showing Mr. Bloomberg a leak-inspired story about his potential candidacy, Mr. La Padula told him, “You need to tighten up your operation.”

Mr. Bloomberg walked out of the meeting, Mr. La Padula said, but called the next day to offer him a job on the campaign. Mr. La Padula took it, leaving his post as chief of staff to Mr. Giuliani’s deputy mayor for operations, Joe Lhota.

“Everybody thought I was a loser. All my friends said, ‘What are you doing? What are you thinking?'” he recalled.

Mr. La Padula and a Democratic operative, Bill Cunningham, were Mr. Bloomberg’s first two political hires, and they stayed with Mr. Bloomberg as he stumbled toward his upset victory over Mark Green.

Mr. Bloomberg paid Mr. La Padula a $100,000 bonus after the victory. But, insiders say, he didn’t get the job he was angling for-chief of staff. Instead, he was given a portfolio that included managing the development of the new city help line, 311, and the office of emergency management.

Mr. La Padula’s real specialty, however, was Republican politics. After graduating from SUNY New Paltz and doing a stint of basic training for the Army Reserve, he volunteered for the campaign of Staten Island Representative Susan Molinari in 1992. A year later, he was managing the Staten Island and Brooklyn field offices for Mr. Giuliani’s second shot at the Mayoralty.

Under Mr. Bloomberg, Mr. La Padula served as a liaison to Mr. Giuliani’s shadow administration, speaking daily to members of the former Mayor’s staff. He also pushed Republican political initiatives within City Hall. And he pushed Mr. Bloomberg to take a stand against overdevelopment on Staten Island, where the Mayor won points by promising to stand against builders who tear down single-family homes and replace them with condominium units and townhouses.

“He single-handedly turned around the Mayor’s relationship with Staten Island in the last six to nine months,” said Mr. Bloomberg’s press secretary, Ed Skyler.

Guy Molinari, the former Staten Island borough president, views the departure of City Hall’s most senior Republican staffer with trepidation. “There’s a strong likelihood that Bloomberg will have a Republican primary,” he said. “He’s really going to need somebody close by that can rally the Republican troops by his side.”

Mr. Lhota, Mr. Giuliani’s onetime deputy mayor, said he expects Mr. La Padula to keep in touch with Mr. Bloomberg-and that he hopes the Mayor will listen.

“He speaks into Mike’s right ear while the rest of the staff speaks into Mike’s left ear,” Mr. Lhota said.

Mr. La Padula’s departure will end the Bloomberg administration’s loose connection to the ugliest scandal hanging over the Giuliani administration: the prosecution of a former official, Russell Harding, for spending city money on personal junkets and gifts. Mr. La Padula reportedly traveled to Portland, Ore., on the tab of Mr. Harding’s agency.

“I have fully answered all questions that the government asked of me a year and a half ago and consider the matter behind me,” Mr. La Padula said.

A Planned Exit?

Mr. La Padula and others in City Hall insist that he always intended to leave during Mr. Bloomberg’s first term. But they also say that he clashed with the administration’s Democrats, and that he lost more fights than he won over policy issues from needle-exchange programs-which he opposes-to personnel decisions.

He remained, however, “dog-loyal” to the Mayor, one administration official said.

“He’s very loyal, and he played his leaving right down the middle. He didn’t go out and play games and be cute,” said Mr. Garth approvingly. But after Mr. La Padula vigorously denied rumors of his departure in early November, Mr. Skyler, the Mayor’s press secretary, felt obliged to tell reporters to call him again. “Vinnie made a mistake,” he said. When reporters followed Mr. Skyler’s advice, Mr. La Padula let it be known that he would, in fact, be leaving City Hall for a vice presidency in the public-finance arm of J.P. Morgan Chase.

In a prepared statement, Mr. Bloomberg called Mr. La Padula “invaluable.”

Even Mr. La Padula’s critics inside City Hall acknowledge that Mr. Bloomberg listened to his advice. The problem, perhaps, was that he didn’t always take it.

That pattern was set on Jan. 2, 2002, as the new Mayor and Mr. La Padula rushed to the inauguration of the new Staten Island borough president, James Molinaro. They were reviewing the Mayor’s personal-security arrangements, and Mr. La Padula advised Mr. Bloomberg to get an unlisted telephone number for his private residence.

“He said, ‘Why would we do that?'” Mr. La Padula recalled. “And I said, ‘Well, there will be some people in New York that obviously will be calling you at all hours of the night.'”

“How will my friends call me?” the Mayor asked. “I’ve been listed for 60 years and I’m not going to change that.”

Mr. La Padula turned the matter over to Police Commissioner Ray Kelly, who said he finally convinced the Mayor to get an unlisted number.

But a quick call to directory assistance reveals that the Mayor-always a man who knows his own mind-still hasn’t taken Mr. La Padula’s advice. Michael R. Bloomberg is still listed in the Manhattan directory. Rudy’s Last Man Leaves City Hall, Riles Republicans