An NYPD detective scored freebies and raked in money running a private security company from his precinct. His bosses didn't care.

• Stephen Giaco ran a private-security company registered in his wife's name from a police station.
• He didn't disclose his side hustle, but the NYPD didn't seem to care, a former colleague told Insider.

For years, Deborah Giaco was a beloved technology aide for a small Long Island school district, praised by colleagues for her "warm and caring nature." On paper, though, she was also the owner of a security company that touts ties to the Secret Service and claims to have a roster of trained agents with experience as bodyguards, bomb detectors, hostage negotiators and SWAT team members.

But while Deborah Giaco owned the company on paper, her husband Stephen, then an NYPD detective, was in charge. According to two former colleagues, Stephen Giaco ran the company, D. Sterling, from the Midtown North precinct where he was based, using public resources for his private benefit.

He stashed metal detectors and charged walkie-talkies in the precinct's community affairs office, and gave employees keys so they could walk into what was supposed to be a secure facility and take the equipment to D. Sterling jobs.

D. Sterling has provided security for awards shows, movie premieres, and other events hosted by some of the same institutions that Giaco was supposed to protect in his day job, like Radio City Music Hall and the Museum of Modern Art. On several occasions, Giaco was at the same events in his official capacity, collecting overtime. And he would dole out free tickets to some events to his superiors, a whistleblowing colleague told Insider.

While the ultimate volume of D. Sterling's business isn't clear, contemporaneous notes and other evidence reviewed by Insider suggest it was a huge operation. But according to the NYPD's responses to Insider's record requests, Giaco appears to have violated NYPD policy by failing to disclose his family side gig. NYPD regulations require officers to provide detailed descriptions of their second jobs and get several sign-offs. NYPD records going back 2013 show Giaco never mentioned D. Sterling, even though he sometimes disclosed work for another employer.

The operation illuminates the risks that can arise from police officers' unmonitored off-duty employment. Moonlighting without adequate oversight can mean conflicts of interest for cops — and it can leave them exhausted, potentially putting the public at risk when overworked officers get behind the wheel of a car or use force.

"Off-duty employment is ripe for abuse because if an officer feels they lack supervision, they'll do what other humans do, which is try to skate," said Keith Taylor, a former high-ranking NYPD official.

"I can't imagine an officer getting concert or baseball tickets and then handing those out as incentives or freebies to folks in management," said Ken Wallentine, a Utah police chief and law enforcement expert who has written about off-duty employment. "To me, that just stinks terribly."

The Giacos didn't respond to several voicemails left at numbers listed for them in public databases, and D. Sterling didn't respond to messages sent to its email address.

A detective blew the whistle and Giaco called him "rat boy"

Giaco, who is now retired from the NYPD, ran D. Sterling from his precinct office at least as far back as the 1990s, according to Lance Trent, a retired crime-prevention detective who shared an office with Giaco and witnessed his conduct for years. Trent said he worked jobs for the company, but eventually called him out in an unsigned letter to the NYPD Internal Affairs Bureau in 2002, which he shared with Insider. Among other things, he wrote that Giaco was providing clients — he named seven — with perks that private-sector competitors couldn't.

"His security business has become extremely large for the simple reasons that he can easily provide his clients with extras," like barriers, parking signage, city permits and special treatment, Trent wrote.

Trent said Giaco came into the office one day and described having been confronted by Internal Affairs about the letter. He said he tried to play it cool, but suspected Giaco knew he'd written it. Eventually, Trent said, Giaco took to calling him "rat boy."

"I was blackballed," Trent told Insider. At one point, someone put a small rubber rat on his desk. Even though it was typical for crime-prevention detectives to be offered the chance to move to a community-affairs role, Trent added, "I was passed over seven times because I was the rat."

Midtown North is an enviable place to work. It doesn't have much violent crime, and it's home to some of America's top businesses and tourist attractions like Rockefeller Center. Some cops call it Fort Hook, because officers with a "hook" — a friend in the mayor's office or NYPD headquarters — have an easier time getting assigned there.

As a detective in the community affairs unit, Giaco was essentially an ambassador for the police department. The connections he made on the job helped him find jobs for D. Sterling and land free tickets to events like a 2019 old-school hip-hop show featuring Vanilla Ice that he doled out to a chief, said Trent, who kept detailed notes on the activities he overheard and observed that he shared with Insider.

Insider found that dozens of events in Trent's notes took place when and where he noted them. Trent also identified D. Sterling personnel, and provided reference photos, in the background of events like the 2019 premiere of Jordan Peele's "Us" at the Museum of Modern Art and Nik and Lijana Wallenda's 2019 tightrope walk across Times Square.

D. Sterling continued to use the Midtown North precinct to store its supplies even after Giaco retired in 2017 with support from his old pals at the precinct, Trent said. In photos from 2018 seen by Insider, Detective Mike Dugan can be seen packing up equipment for a D. Sterling employee standing nearby.

In a statement for this article, the NYPD said only, "Det. Stephen Giaco retired in July of 2017" and referred Insider to its patrol guide.

Trent said numerous senior officers were aware of the operation, but turned a blind eye. Mark Iocco, a former NYPD inspector assigned to the precinct who retired last year, once said that "there are three units in Midtown North: community affairs, crime prevention and D. Sterling," Trent recalled. Iocco didn't respond to calls or emails.

At a 2016 Alicia Keys concert in Times Square, Trent wrote, "Sterling had 39 guys." Four men in D. Sterling shirts are visible when an ABC cameraman followed Nik Wallenda down a short corridor after his high-wire act.

Despite efforts to combat corruption, policing in New York has been rife with misconduct. The current deputy mayor for public safety, Phil Banks, was named in FBI affidavits after failing to pay taxes on over $500,000 in rent and suspicious cash deposits, according to The City. (The mayor's office has defended Banks; Banks' lawyer told the New York Post in 2018 the money came from rent, an inheritance, and "poker games.")

Private security is a common second job for cops, two former NYPD officers told Insider, and Giaco probably wasn't the only one to do it under-the-radar.

"In all the precincts in Midtown…there were people that had security companies," one said. "I don't know what they net, but I'd say the big guys, their gross receipts were definitely seven figures."

Trent said his negative experience with Internal Affairs in 2002 made him hesitant to reach out again, even though D. Sterling's activities continued until Trent's 2021 retirement.

Everett Stern, a whistleblower-turned-security consultant who has worked with Trent, said he urged local and state authorities to investigate his claims and provided an intelligence report that summarized them to several agencies, including the New York Attorney General's office and the current commander of the Midtown North precinct. They either didn't respond or passed the buck, Stern said. The New York AG's office didn't respond to a request for comment.

"Not to at least open an inquiry or get back to me and say, 'Do you have more information,' or 'Who's the whistleblower,' it doesn't make sense to me," Stern said. "Why would they not do that?"

Police officers' second jobs can create risks

For years, groups like the International Association of Chiefs of Police have sought to spread awareness of the risks of not properly regulating and supervising police officers' off-duty work. But not all departments have heeded the warnings, and scandals persist.

In Los Angeles, police captain Cory Palka wound up at the center of a firestorm after the New York Attorney General learned that he had tipped off CBS — where he moonlighted as private security — to a criminal complaint made against its CEO Les Moonves. He is reportedly still under investigation. Palka did not respond to a request for comment.

And in Miami, police watchdogs wrote in 2019 that cops appeared to bend the rules to work at bars and clubs that officially barred their employment.

"The majority of security companies in New York City are heavily tied in with law enforcement, not just in the NYPD, but also in the feds," said John Macari, a retired lieutenant. "A lot of that stuff's not authorized."

And issues posed by off-duty employment aren't unique to large departments. Wallentine, the Utah police chief, said he knew of a city where an officer was caught tipping off the manager of an event hall where he or she had worked off-duty to be wary of serving underage or inebriated patrons at a particular event because undercover police would be present.

Second jobs can also leave officers exhausted and play a role in bad decisions — with fatal consequences. Mohamed Noor, the Minneapolis police officer who was convicted of manslaughter for killing Justine Ruszczyk Damond, went from working a seven-hour private security shift to a ten-hour police shift. He was about seven hours into the shift when he shot Damond.

Use of force isn't the only risk when cops work too long. New York City's Department of Investigation, which tracks city government conduct, found that police overtime correlated with lawsuits, civilian complaints, and car crashes.

The department said it couldn't analyze the impact of cops' second jobs because the NYPD "does not require officers to report those hours and does not monitor or track them."

"Ultimately, the agency — by allowing that off-duty employment to occur — is taking a risk," said Taylor, the former senior NYPD official.