Rikers Island Lawyer Seeks Meaningful ‘Last Chapter’ in Career

Paul Shechtman, after 25 years in private practice representing law enforcement officers, lawyers, politicians, Wall Street executives, and celebrities such as the rapper Lil’Kim, said he was ready for a change.

It was quite a change.

New York City’s Department of Correction on Aug. 9 announced Shechtman as its new deputy commissioner and general counsel, a role that makes him the top lawyer for the jail system and its largest complex at Rikers Island.

“This is a chance for me to do something meaningful in a city I really care about,” Shechtman said in an interview from his office, where he’s coming each day as required by a mayoral mandate. “I wanted to have a last chapter in the public sector. My kids were pushing me to do it and not just talk the talk.”

Shechtman, 73, has avoided a path typical for many lawyers his age—retirement. His move to an in-house legal job is also unusual for someone who has spent almost a half-century practicing law.

It was Mayor Eric Adams’s chief counsel, former Wilmer Cutler Pickering Hale and Dorr partner Brendan McGuire, who recommended Shechtman for his new position.

Shechtman said he called McGuire, a friend and fellow former federal prosecutor, earlier this year to offer up his services. “I asked if they needed a good lawyer—maybe I should’ve said an old lawyer,” he quipped.

But Shechtman said his skills—sharpened over four decades of legal practice in myriad high-stakes battles—are still sharp.

“You can be productive in your seventies and take on new challenges,” he said. “And I think my wife is happy that I’m out of the house.”

Paul Shechtman

The Harvard Law School graduate and Rhodes Scholar who once clerked for former U.S. Supreme Court Justice Warren Burger succeeds Asim Rehman, who in March was named chief administrative law judge and commissioner of New York’s Office of Administrative Trials and Hearings.

Shechtman spent nearly the first decade of his legal career as a state and federal prosecutor in New York. He was also the state’s criminal justice director from 1995 to 1997 under former Gov. George Pataki.

He’s written about the need for bail reforms and sought to correct wrongful convictions.

“I’ve been an advocate for a middle path,” said Shechtman, adding that his biggest concern about the criminal justice system is the pendulum for executive or legislative action to swing too widely in one direction or another.

Rikers Island

The Rikers Island jail complex for years held individuals facing misdemeanor charges on $500 bail, Shechtman noted.

“That’s crazy,” he said, citing the meaninglessness of holding individuals facing minor charges, many whom were freed by organizations that posted their bail.

Rikers is often the first item on Shechtman’s docket each day, he said.

The facility, hit hard by staffing shortages related to the coronavirus pandemic and coping with a series of inmate deaths, is subject to a federal monitor tasked with overseeing an overhaul of in its operations.

New York’s Department of Correction said earlier this year it was taking steps to improve the facility after that monitor, prison reform expert Steve Martin, accused the city of stymieing his efforts.

A surprise visit this week by a delegation of city officials found the Rikers complex in better shape than expected, in part due to improved staffing levels, although conditions are still dangerous, according to Bloomberg.

Shechtman, who is working closely with the city’s corrections Commissioner Louis Molina, expects to be able to show more progress later this year and avoid a federal takeover of the facility.

“When I was in private practice, my clients would say to me, ‘Think outside the box,’” Shechtman said. “I would say to them, ‘I don’t. You can either plea, plea and cooperate, or go to trial. All I can do is get you in the right box.’”

As Shechtman saw it, if a client wasn’t in the right box, they were going to be “harmed greatly.”

Private Practice

Shechtman spent the bulk of his career at Stillman Friedman & Shechtman, a New York-based litigation boutique where he was a name partner.

He left that firm in 2011 to become a partner at Zuckerman Spaeder. Ballard Spahr acquired Stillman & Friedman, as his former firm was renamed, in 2013.

In 2016, Shechtman and Barbara Jones, a former federal judge in New York, left Zuckerman Spaeder to become partners at Bracewell.

A Bracewell spokesman confirmed that Shechtman left the firm at the end of May.

Jones remains at Bracewell. Shechtman said parting ways with his longtime colleague was the toughest part in his decision to leave private practice.

He said he’s getting used to not writing briefs and staying out of the courtroom.

“I don’t miss representing individuals—it’s really hard—you’re getting people at the most difficult time of their lives,” Shechtman said. “Their lives were in my hands.”

Corrections Connections

It was at Bracewell where Shechtman represented Norman Seabrook, a former head of New York’s corrections officers’ union, who was arrested in 2016 on corruption charges.

An initial bribery trial involving Seabrook ended with a hung jury in 2017. Seabrook was eventually convicted the following year and sentenced in 2019 to five years in prison and ordered to pay $19 million restitution.

“My understanding is the unions were told I was coming, and they didn’t complain,” Shechtman said when asked about potential conflicts in his new role. “I don’t think I have any enemies there.”

A longtime lecturer at Columbia Law School, Shechtman oversees roughly 15 lawyers at the Department of Correction.

He said he will stay in his current role as long the city and Adams want him.

“As long as I’m capable of doing this job and it remains interesting and I’m able to help, I’m going to stay,” Shechtman said. “They may have to push me out in a wheelchair.”