Jimmy Oddo’s midlife crisis

Jimmy Oddo is the only person I’ve ever seen put glasses on to make a point. He grabs them from his cluttered desk and shoves them on his face, the only way his 52-year-old eyes can focus on the pages he reads – and he’s reading more pages lately than he has since law school, it seems. The glasses, the dark suit, the long, white beard – the Staten Island borough president looks more like a scholar of medieval texts than a politician. But he is a politician, just one who has been recently freed from the tyranny of electoral politics.

“There’s a phrase that I came upon in this book that I am reading,” Oddo said, glasses on, rifling through pages covered with yellow highlighter and Post-it notes. “The phrase is ‘functional fixedness’ … basically it says people do what they do how they do it because that’s the way they’ve always been doing it. And that’s what we run into, time and again. I think that’s the biggest single frustration about the job today.”

Oddo gets frustrated easily, and he’s not one to hide it. Those frustrations almost led him to quit his job this year, just months after being re-elected in a landslide. But Oddo held on, more driven than ever to deliver for the people of Richmond County.

Staten Island is the borough with the highest rate of native New Yorkers, including the borough president. Oddo was born in 1966 in the mid-island neighborhood of Old Town. He went up north for college, to Fordham University in the Bronx, then completed law school a little closer to home, at New York Law School in lower Manhattan. He dreamed of becoming an FBI agent, but fell in with New York City Councilman John Fusco, joining his office as an aide in 1992 and starting on almost the exact same day as another City Council aide, Christine Quinn, who quickly became Oddo’s friend and eventually was elected to the body and then became speaker. Fusco stepped down to become a judge, and Oddo ran for his seat and won in February 1999. He kept the seat for 14 years, before being term-limited out in 2013. He ran for borough president and won. Then in 2017, things got hard.

“The fourth year was the most frustrating for me,” Oddo said.

Because after three years of a productive relationship with New York City Mayor Bill de Blasio, the city’s bureaucracy was wearing him thin. Oddo and de Blasio have been friends since their days serving together in the council. They share an Italian heritage, a love for baseball, and – despite Oddo’s Republicanism – a trust in the power of government.

But Oddo was feeling screwed. City Hall just didn’t seem to share his obsession with street maintenance. So Oddo kept making a racket about the bevy of public agencies and private actors that cut into Staten Island’s beloved asphalt and did a shoddy job replacing it after their work was completed – leaving bumps and potholes. The uneven streets are a minor inconvenience to some, but an incredible, unrighteous disrespect to Oddo, the man of the people whose job is to remind the mayor that Staten Island exists. But City Hall didn’t seem to listen.

“Everything is personal to me.”

And then there was the ferry – de Blasio’s supposed “five-borough ferry system” that’s only planned for four boroughs. Yes, Staten Island has the slow orange ferry linking The Battery to St. George, and City Hall says it is still looking into expanding the NYC Ferry network to the borough, but Oddo wanted the sleek, fast boats to open up new commutes for island residents who work north of Wall Street, and he wanted it last year. But de Blasio didn’t come through.

“Up until three weeks before Election Day, I was convinced the mayor was going to say, ‘All right, you got it,’” Oddo said. “And I didn’t. And it angered me.”

That anger weighs heavily on Oddo.

“For better or for worse, long ago with me, I’ve blurred the lines between business and personal,” Oddo said. “Everything is personal to me. I think it’s one of the reasons why I’m an effective elected official. It makes me half insane sometimes, because I do take everything so personal.”

Quinn, the former speaker, sees it the same way.

“It is not a job to him, which is both why he has fun and why he tortures himself. I worry sometimes about the torture part,” she said. “If he is driving around Staten Island and gets into traffic, he is not just like, ‘Oh, I’m going to be 10 minutes late to see (his wife) Kim,’ he’s like, ‘Oh my god, our entire traffic work has failed.’”

Stressed out by his job at Borough Hall, opportunity knocked at the courthouse next door. Judge Robert Gigante would turn 70 years old this year, meaning by law, he’d have to step down from leading Staten Island’s Surrogate’s Court. It’s a plush job, and if elected, Oddo would serve a 14-year term – serving the people of his beloved borough and arbitrating disputes over estates, adoptions and guardianship. Oddo hadn’t hidden his interest in the position, telling the Staten Island Advance in February 2017 that he was considering a run for the post. But with an election scheduled for November 2018, he had time to decide. And agonize.

Oddo took to self-help and leadership books. “Drive.” “Extreme Ownership.” “Barking up the Wrong Tree.” “The Subtle Art of Not Giving a F*ck.” He was reading them all. He got re-elected easily last year. Then it became time to make a decision. Serve just one year and run for Surrogate’s Court or stay in his job as borough president. Normally clean cut, Oddo began to grow a beard.

“It was like an outward manifestation of the inner conflict I had about making the decision to stay or go,” Oddo said. “Because for as long as I had a beard on, I couldn’t stand on the steps of the courthouse and say, ‘I’m going to run for Surrogate.’”

Oddo struggled with the decision for nearly five months. But by March, he came to the realization that being a judge – like his wife, Kim, who is a judge in Queens Criminal Court – isn’t for him.

“I want to know that whatever I’m doing has true meaning,” Oddo said. “And true meaning for me means impacting lives in some way. I want to squeeze life out of every moment, and that, to me, wasn’t it.”

So Oddo, the tireless advocate, will stay at Borough Hall, hounding the de Blasio administration to speed up development on Staten Island’s West Shore, to pave the roads and to bring a new ferry to his borough. Oddo’s second and final term goes until the end of 2021, but he already has his eye set on another job.

Mayor? “Who would want the job in this era? I know I wouldn’t.” Oddo said. “The job that I see as the perfect job is the one that allows you, after 30 years of fighting the bureaucracy from the outside, to be on the inside and implode it. And I think (Deputy Mayor for Operations) Laura (Anglin) is in that position.”

And why not? Even in true blue New York City, Oddo has the bona fides to join. He couldn’t muster a vote for Donald Trump in 2016, writing in Ronald Reagan instead. And his dream has Democratic backing.

“It is not a job to him. Which is both why he has fun and why he tortures himself.” – former New York City Council Speaker Christine Quinn

“He would be a massive benefit to any administration, Republican, Democrat or Independent,” Quinn said. “That is the next best job for Jimmy. There is no question.”

Manhattan Borough President Gale Brewer, a Democrat who has worked closely with Oddo, backs him too. “He should be first deputy mayor of operations,” she said. “I think he’s a first-rate human being, first-rate public servant, and it would be great if he could run the city of New York.”

But Oddo is in no rush. After five months of growth, he shaved the beard, and it’s back to work as usual, sticking up for his 475,000 neighbors. Oddo said he’s the right man for the job.

“If I wasn’t here, and I wasn’t as maniacal as I am, and I didn’t build a team that I built, who cares as much as they do,” he said, “Staten Island would be in a much worse place.”