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Ex-New York AG Lawyer Claims ‘Misconduct’ by Top Prosecutor



For two years now, a senior lawyer at the New York Attorney General’s Office has been trying to get top bosses to listen to his claims that the agency’s chief prosecutor has potential conflicts of interest and hid unsavory professional relationships.

But instead of landing that chief prosecutor in hot water, it was the senior lawyer who made the complaint, John Oleske, who found himself out of a job.

Now, as the New York Attorney General’s office tries to dismiss Oleske’s objections as a personal grudge between one employee and another, the office is reckoning with the fact that while some of Oleske’s claims are unproven, some are verifiable. And the New York AG dismissed Oleske after he raised concerns about the chief prosecutor, a longtime bureaucrat in New York politics: José Maldonado.

The first time Oleske sounded the alarm about Maldonado, he found himself in administrative hell, with executives putting Oleske on forced medical leave for months, citing “erratic” behavior and mental health issues. When Oleske tried to bring up potential issues with Maldonado again in October, the AG’s office simply fired Oleske.

That decision came shortly after The Daily Beast published stories based on leaked records that Oleske gave to the Manhattan District Attorney’s Office, which he hoped would investigate the sister law enforcement agency.

But early last month, Oleske met with federal investigators at the Southern District of New York and handed them a 74-page report he compiled on Maldonado—along with his official work laptop as evidence.


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The New York AG’s decision to fire Oleske marks a turning point in the former prosecutor’s crusade to become an unlikely whistleblower. Oleske previously led trial teams that won some of the AG’s biggest recent cases, including a massive $523 million settlement last year from Teva Pharmaceuticals for fueling the nation’s opioid crisis.

But he is now persona non grata at the office and viewed with deep suspicion, according to several people who spoke on condition of anonymity. Two people chalked up his concerns as nothing more than a “personal vendetta.” Another called his SDNY report a “manifesto.” His sternly worded termination letter cited his “insubordination.”

The target of his ire, Maldonado, is the chief of the AG’s powerful criminal division. And over three decades, Maldonado has risen through the ranks of New York’s legal realm.

After cutting his teeth at the DA’s office during the harrowing 1980s crime wave, Maldonado became a favorite of then-Mayor Rudy Giuliani—appointed to a panel that one local politician said was reserved for the mayor’s “cronies.” He became a go-to city bureaucrat, weaving through mayoral administrations in various capacities.

Maldonado now oversees all criminal investigations from the state’s top law enforcement office, the same agency whose civil division is separately putting former President Donald Trump on trial for bank fraud—and winning.

Maldonado has been part of AG Letitia James’ team from the very start of her tenure in 2019. But as the years went by, Oleske—who didn’t report to Maldonado—grew frustrated with the way the criminal division was run. For example, Oleske was angry at the AG’s failure to indict the Rochester police officers who arrested Daniel Prude, put a spitbag hood over his head, and stood by while he died on a frozen street. (A grand jury voted not to indict, and the AG’s office took the notably transparent step of publishing its secret transcripts.)


New York Attorney General Letitia James leaves the courtroom in New York State Supreme Court in Manhattan on Nov. 13, 2023.

Brendan McDermid/Reuters

In May 2022, Oleske turned his investigative chops on his own coworker, only to discover what his report calls “apparently serious misconduct” due to “falsifying his resume and hiding conflicts of interest with OAG’s enforcement targets.”

When The Daily Beast asked the AG’s office about how it handled Oleske’s internal reporting, the agency stated it didn’t ignore them. “The office reviews any complaint or allegation that’s made against any member of the office, including those made here. The office takes every complaint seriously and has always taken appropriate action when warranted,” a spokesperson said.

Although his full report details a litany of allegations, The Daily Beast is only documenting what we were able to independently verify about the high-ranking prosecutor.


What isn’t in dispute is that Oleske discovered allegations against Maldonado which, until now, have never been made public.

In 2020, when Maldonado was already at the AG’s office, he was accused of racism in an ongoing federal discrimination lawsuit in Manhattan. John Coombs, the past president of the city’s Black firefighters association, wrote a sworn statement that specifically called out the prosecutor for the alleged damage he did back when Maldonado was at the New York Fire Department.


In the statement, which was filed in a public court record as part of a class action lawsuit against the City of New York, Coombs recalled urging then-FDNY Commissioner Daniel Nigro to fire Maldonado, who was the chief’s senior policy adviser at the time. Coombs claimed Maldonado had used his prior role to merely rubber-stamp the previous commissioner’s discriminatory policies.

José Maldonado

NYC Special Narcotics Prosecutor’s Office

“Previously Mr. Maldonado had served as Associate Commissioner for Compliance, where he supposedly oversaw FDNY’s effort to enhance its recruitment, diversity, and EEO programs. I warned Mr. Nigro that Mr. Maldonado instead had been willing to do anything that Daniel Shacknai had asked of him, including actions that had blocked the advancement of African Americans,” Coombs wrote.

In response to The Daily Beast’s questions about these previous complaints, the AG’s office dismissed the allegation as an unverified and unspecific claim—one that was meant to support the certification of a class action lawsuit that a judge refused to give class action status.


But an old accusation of racism is hardly Oleske’s only gripe. Oleske also complained about the way Maldonado seemed to hide his past involvement with an entity called the Brooklyn Golf Alliance. The nonprofit has landed $40,000 from the city since 2019 to engage in “community programming” and youth golf workshops, according to files reviewed by The Daily Beast. The group is an offshoot of the business vendor that runs Brooklyn’s municipal Marine Park golf course—one that landed a 20-year, $10 million deal to run the 18-hole waterfront fairway and at one point, was guzzling more than 20 million gallons of city water annually and shelling out a humongous $140,000-a-year water bill.

In Oleske’s view, one potential problem is that the nonprofit’s operations might land under Maldonado’s purview as a prosecutor. Although the AG’s charities bureau sits within the agency’s civil side, one former prosecutor noted, the office can launch criminal investigations into nonprofits.

Maldonado was listed as a board member on the nonprofit’s yearly tax filings from 2017 until 2021. The group’s website previously featured Maldonado, but he no longer appears on the page. However, Maldonado didn’t include his involvement with the Brooklyn Golf Alliance on his annual ethics disclosure forms for years.

The Daily Beast filed a public records request with the New York State Commission on Ethics and Lobbying in Government. The documents show that Maldonado didn’t mention any involvement with the Brooklyn Golf Alliance in 2018, 2019, or 2020. And he only belatedly included it on an amendment to his 2021 form—one that no one would think to pull unless specifically requested from the state office.


When he finally did update his disclosure form, Maldonado listed his involvement with BGA under “positions of authority.”

Reached last week, the nonprofit claimed Maldonado no longer worked there.

“I don’t have the exact date, but it was when he began his current employment,” BGA’s treasurer, Michael Weiss, told The Daily Beast.

But that doesn’t appear to be true. Official documents place Maldonado at BGA more than two years after he joined the AG’s office. The AG’s office told The Daily Beast that Maldonado quit BGA in 2022, when he was caught failing to disclose his involvement.

Maldonado’s involvement with the group raises another potential conflict of interest: The AG also cracks down on abusive property owners—a particularly challenging job in a place like New York, where rentals are the norm and tenants frequently get screwed. The golf nonprofit’s board also includes Jeffrey Dunston, head of Northeast Brooklyn Housing Development Corporation—which has the dubious distinction of being rated “second-worst” private landlord in the city by James herself in her previous role as the city’s public advocate.

In response, the AG’s office noted that it regularly targets bad landlords—but an employee’s mere association with someone doesn’t indicate wrongdoing.

Still, there’s a third issue that could raise eyebrows. BGA’s president is none other than Lucius Joseph Riccio, a former New York City transportation commissioner—and the husband of Donald Trump’s longtime personal secretary Rhona Graff. The couple got married in 1993 at the Plaza Hotel, which was owned by Trump (hence his iconic Home Alone 2 cameo).

Former President Donald Trump attends the Trump Organization civil fraud trial.

Former President Donald Trump attends the Trump Organization civil fraud trial, in New York State Supreme Court in Manhattan on Nov. 6, 2023

Jabin Botsford/Pool via Reuters

Maldonado’s tangential connections to Trump particularly alarmed Oleske, whose report details his concerns that Maldonado was somehow in a position to exert influence over the office’s early inquiry into potential criminal charges against Trump.

However, two sources with knowledge of the matter insisted that Maldonado never oversaw any aspect of the Trump investigation. A third person with extensive knowledge of the Trump investigations, which were eventually handled by the DA, shrugged off any concern that the tenuous connection would interfere with ongoing law enforcement operations against the former president.

A fourth person, who previously worked at that office, suggested that the disclosure failures raise fair questions but don’t present clear conflicts of interest—a situation that’s either evidence of a stupid mistake or laziness by an experienced public official who should know better.


Then there’s Oleske’s other contention—that Maldonado hid his involvement in yet another industry he might oversee as the AG’s top prosecutor: private garbage companies.

Manhattan’s private waste hauling is notoriously fraught with problems. It’s an industry long dominated by mob control and frequently in the news for running over pedestrians. And each time that happens, New Yorkers call for stronger safety rules and a regulation overhaul, as they did when a private carting truck killed a Jewish architect cycling last year in Brooklyn—then sped off.

The problems are so extensive that they led to an award-winning ProPublica investigation, “Trashed,” that examined corrupt practices, an attempted crackdown, and a lobbying scheme to thwart industry reform.


The very year that investigation came out, Maldonado was a “senior adviser” to the lobbyists at the center of it all: New Yorkers for Responsible Waste Management, a now-defunct business league incorporated as a 501(c)(6) nonprofit.

As ProPublica pointed out, the trade association’s secretary-treasurer at the time was Ray Shain, a convicted felon who was disbarred in New York 20 years ago after pleading guilty to bribery and kickbacks that defrauded public schools in Queens to the tune of $6.3 million. It’s exactly the kind of nonprofit Maldonado would police. Look no further than its bylaws, which bear the stamp of the AG’s charities bureau, the law enforcement component that serves as an industry watchdog.

And yet, neither Maldonado’s public LinkedIn page nor the résumé he submitted to the AG make any mention of his past involvement. Instead, he disclosed it in a 2018 form to another state agency—records that aren’t readily available online—in which he said he earned between $20,000 and $50,000 working for the industry group that year.

It was a good fit, given his past position of influence in that industry. Maldonado was once referred to as “Gotham City’s top trash cop” by Waste News, a trade publication that in 2003 documented the way he used his position as chairman of the city’s Business Integrity Commission to give those private companies a major victory by deregulating the industry. Maldonado was quoted as saying that he altered the garbage pricing system to create “an environment where carters can make a profit and where customers will end up benefiting from increased competition.”

He continued that kind of work at NYRWM, at one point co-authoring an editorial piece sprinkled with corporatespeak about “solution-oriented initiatives,” where he professed the need to “overcome the dark legacy of generations past” and stressed that “it’s too easy to believe the worst about the waste services industry.”

Reached last week, Shain—NYRWM’s treasurer who was previously convicted of bribery—would not elaborate on the nature of Maldonado’s work there. “The organization is fully disbanded. At this point there is no one to ask, and I have no authorization,” he wrote.

As the head of the AG’s criminal division, Maldonado is positioned to greenlight or refuse a potential sweep of the very industry he used to represent. The law enforcement agency has the power to do so, but has mostly stuck to civil penalties. James recently nailed a recycling company for illegally dumping cathode ray tubes and tons of other electronics in far upstate New York. One of her predecessors, Eric Schneiderman, sued trash collectors for rigging bids and fixing prices. And one of his predecessors, Eliot Spitzer, tried to stop one company from establishing a powerful rubbish monopoly.


In response, the AG’s office countered that Maldonado did this nonprofit work in his capacity as an outside adviser while briefly operating his own consulting firm—and that attorneys regularly build a diverse list of clients. But the office stressed that no conflict has arisen, and if one did, it would get dealt with through proper channels.

Still, this wasn’t the first time Maldonado went through the revolving door between industry regulators and the business world.


During a previous stint at the AG’s office, Maldonado was the deputy attorney general for the AG’s Medicaid Fraud Control Unit, which the office describes as “the largest unit” within the criminal division. In that role, he oversaw a settlement that forced an AmeriChoice subsidiary to pay back $2 million in state funds it received for medical services in Brooklyn but never really delivered. But in 2003, he left government to join AmeriChoice as its “vice president of integrity and compliance.” His résumé shows that he stayed at the UnitedHealth subsidiary for six years.

A Newsday article about his career shift noted that “AmeriChoice is a major contractor with government health insurance programs such as Medicaid”—which makes it all the more startling that, in 2021, when he was now supervising the AG’s criminal division, a sizable stock market investment suddenly appeared on his mandatory state disclosure form.

Maldonado revealed his ownership of some $150,000 to $250,000 in UnitedHealth Group company shares. The financial stake in the company made up nearly half of his listed investments.

The AG’s office noted that Maldonado had received the investments back when he still worked for the company. However, records pulled by The Daily Beast show that he did not include them in his 2018, 2019, or 2020 state disclosure forms.

As for the conflict of interest concerns, the office noted it has continued to target UnitedHealthcare with civil enforcement actions—suing it last year to block a proposed company merger and scoring a $14 million settlement the previous year for improperly denying insurance coverage.


On Sunday night, the AG issued a statement to The Daily Beast making clear that the office stands behind its top prosecutor.

“Jose Maldonado is an incredible public servant who has dedicated his career to protecting New Yorkers and fighting for justice. As Chief Deputy Attorney General of the Criminal Division for the past five years, Jose has overseen some of our most impactful work protecting New Yorkers, including our nursing home investigations. He has always conducted himself with the utmost integrity and care, and I’m confident he will continue this great work for years to come,” James said.


When Oleske first surfaced these discoveries internally, he turned to the AG’s second-in-command: First Deputy Attorney General Jennifer Levy.

Emails show that Oleske flooded her inbox with increasingly anxious emails, suggesting the office somehow get another law enforcement agency involved. After one quick meeting in her office in downtown Manhattan in June 2022, Oleske told The Daily Beast, he quickly returned for a follow-up—only to notice that agency security personnel were now standing outside her doorway.

When Levy directed his concerns to the agency’s human resources, Oleske veered hard left—thinking his own colleagues were abruptly turning against him. Instead of looping in HR, Oleske fired off an email to an attorney on the agency’s ethics committee. The next day, the agency forced him to stay home—and followed up with a stark letter later that month.

“It has come to our attention that you have engaged in concerning conduct which has raised serious health and safety, as well as operational concerns on the part of your coworkers and agency management. You have been observed to have engaged in a pattern of erratic, agitated, irrational, and disruptive behavior in the course of recent interactions and communications with colleagues and agency management,” the letter said. “Based on these accounts, and in full consideration of your work history, we have reason to believe that your recent troubling behavior may be due to a physical and/or mental impairment.”

Oleske said he was forced to burn through months of accrued paid time off, only to return to the office as if nothing ever happened.


“My first thought was: I must have been right about José being crooked. They’re trying to get rid of me under this threat that they’ll say I’m crazy. This is Soviet-style, sick kind of shit,” he said.

The Daily Beast asked about how the AG handled this matter, and the agency replied that “the office does not discuss personnel matters.”

Shortly after he returned, AG leadership in January reassigned Oleske away from his opioids cases and put him on tobacco enforcement work, according to internal emails reviewed by The Daily Beast. Oleske saw it as a slight. As the months went by, Oleske waited for the right time to go public.

The day before Halloween this year was a Monday. At 10:43 a.m., Oleske emailed more than a dozen AG colleagues with his draft SDNY report, accusing the office of “trying to intimidate and extort me into silence rather than addressing and resolving the problem inherent in Mr. Maldonado’s false statements about his work history and business relationships.”

Half an hour later, Oleske was formally fired and “barred from entering the premises.”

“This letter will serve as official notice that your exempt, at-will appointment to the position of Assistant Attorney General with the Office of the Attorney General is terminated effective immediately. This termination is based upon your insubordination, including your refusal to answer questions and cooperate with an internal employment review,” HR Director Jenna Moran wrote.

When the AG general counsel’s office emailed him a week later, instructing him to mail back his work ID card and other work gear in a pre-addressed shipping box, Oleske let them know he couldn’t turn over his laptop. He’d already handed it over to the feds.


“I have already surrendered all OAG property in my possession to Eric Blachman, Special Agent in Charge of the US Attorney’s Office for the Southern District of New York. Contact him directly with any further inquiries,” he shot back. “DO NOT CONTACT ME AGAIN.”

Source: The Daily Beast

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