Sheldon Silver’s legacy as one of the most notorious “three men in a room”

Albany’s most notorious “three men in a room” is now down to two – the remainder of whom are all but banished from the Capitol where they once wielded undue influence that has been dismantled in recent years by the unveiling of corrupt and sexually deviant behavior either practiced or concealed by the trio. 

The men – former Assembly Speaker Sheldon “Shelly” Silver, former Gov. Andrew Cuomo and former State Senate Majority Leader Dean Skelos – exemplified the smoke-filled back room dealing that has dominated state politics for decades, if not centuries, and was said to have created a culture of self-serving secrecy and patriarchy. 

Silver died on Monday at the age of 77 in a Massachusetts federal prison where he was serving out a six-and-a-half-year sentence for fraud, extortion and money laundering. Skelos is two years into his four-year sentence on corruption-related charges in a separate case. And Cuomo, who once fondly referred to the group as “the three amigos,” is facing a slew of ongoing probes related to sexual harassment, his personal book deal and pandemic nursing home policies.

Silver’s epic fall from grace marked the beginning of a cultural shift at the Statehouse that stripped the three men of their power. 

Up until his arrest in 2015 on a series of corruption and money laundering charges, Silver was known as a soft-spoken but arm-twisting deal-maker whose two decades as speaker was one of the longest tenures in Assembly history. Years after his conviction, colleagues continued to sing his praises, touting his legacy on education and LGBTQ rights.

On a personal level, Silver represented a fading breed of New Yorker who was raised and lived his entire life within a several block radius on the Lower East Side where his Russian-Jewish parents immigrated to in the early 20th century. Until he was finally imprisoned at the age of 76 in August 2020, Silver was regularly seen visiting the nabe’s iconic Jewish establishments, one of which, Ratner’s, reportedly served as a de facto office where he brokered illicit deals that landed him behind bars.

In the wake of his death this week, Silver was remembered for his “complicated legacy.”

“If you look at what he did for early education and education in general, and you look at what he and Joe Bruno did here in the Capital Region regarding not only Sematech, Nano Tech and GlobalFoundries – our region has some of the best growth in the State of New York. But unfortunately it's tarnished because of what he was convicted of and what he spent the rest of his life in prison for,” Assembly Member John McDonald told CBS 6 in Albany.

Silver’s stunning 2015 arrest threw the Capitol into turmoil just after the start of the legislative session. It came with a sweeping federal indictment that laid out years-long corruption schemes he engineered to the tune of millions of dollars. 

In one piece of Silver’s two-pronged plot, federal investigators found that he urged developers to hire a law firm run by his former Assembly counsel, Jay Arthur Goldberg, who paid him about $1 million in fees over the years in exchange for referrals. Among the real estate clients who hired Goldberg’s firm, Goldberg & Iryami, at Silver’s behest were Glenwood Management, a luxury apartment developer, and The Witkoff Group, which had business interests in Silver’s district in downtown Manhattan. As part of the deal with Glenwood, Silver met with its lobbyists and fought legislation that would benefit the company.

He also allegedly steered mesothelioma patients to another firm, Weitz & Luxenberg, who in turn paid him more than $3 million over the years. Silver then directed $500,000 in state grants to the cancer doctor, Robert Taub of New York-Presbyterian/Columbia Medical Center, who sent him the patients.

Like Cuomo, the law enforcement revelations forced a swift fall from grace for Silver. He tendered his resignation as speaker on Jan. 30, 2015, a week after his arrest, but kept his Assembly seat. Silver was convicted in November that year on all seven charges of honest services fraud, extortion and money laundering related to his schemes, and was sentenced to 12 years in prison. He appealed the decision and was reconvicted in 2018. In a third appeal in 2020, his charges related to the real estate developers were thrown out and he was given a six-and-a-half-year sentence plus a $1.75 million fine. 

Silver’s federal indictment proved what many in Albany had suspected of the speaker for more than a decade. 

His personal injury law practice, for years, was the subject of speculation about whether it was ethically sound for him to make money on the side without conflicting with his state responsibilities. He helped found Weitz and Luxenberg and remained on the firm’s payroll during his time in the Assembly, while claiming he could not reveal his salary or clients. And in a particularly bizarre case that demonstrated Silver’s commitment to avoiding public scrutiny, Silver blamed another lawyer with the same name for fighting off the construction of low-income housing in his district on the Lower East Side. Silver claimed that the letters he sent beginning in the 1970s on behalf of the United Jewish Council, which opposed the project, were in fact sent by a Sheldon E. Silver from Brooklyn. The identity debacle was brought to light in a New York Times article in 2014, after the Brooklyn lawyer died, and while the land dispute was still ongoing. 

In addition to the corruption charges, Silver was accused of helping foster a culture in Albany that allowed Cuomo’s behavior to thrive and remain hidden for years.

In 2000, Silver survived a coup led by then-Assembly Majority Leader Michael Bragman and others who accused him of operating a “dictatorship” that catered to lobbyists and left lawmakers in the dark. The fallout put an exclamation point on the very tactics the coup sought to dismantle – in the wake of Silver’s victory, Bragman was stripped of his title, budget, office and staff. 

In yet another example of Silver’s unyielding power over the Assembly, he twice killed plans championed by New York City Mayor Michael Bloomberg. In 2005, Silver refused to approve a stadium on the West Side of Manhattan that many hoped would bring the 2012 Olympics to the city. And in 2008, he nixed Manhattan congestion pricing with little explanation, despite the City Council and then-Gov. David Paterson’s support of the plan.

Silver was also accused of covering up sexual misconduct allegations against two of his allies. He refused to bring an ethics investigation against former Assembly Member Vito Lopez, who was accused by two former female aides in 2013 of a pattern of sexual harrassment and groping. A decade earlier, Silver’s office allegedly sent a threatening letter to a woman who accused Assembly lawyer Michael Boxley of raping her. The woman, Elizabeth Crothers, now co-founder of the Sexual Harasssment Working Group, said Silver blew her off when she told him about the alleged rape in the early 2000s. When she publicly criticized Silver two years later, his office sought to silence her, according to reports.

Skelos’ and Silver’s 2015 indictments not only left Cuomo without his staunchest allies but shed light on his failure to execute the ethics reforms that were, ironically, supposed to be a hallmark of his legacy.

Cuomo disbanded the Moreland Commission that was set up to investigate corruption a year before the indictments, which repeatedly referenced the group’s work. In the wake of the charges, Cuomo was heavily criticized for shuttering the commission, which was taken over by then-U.S. Attorney Preet Bharara, setting off a rivalry between the two that has bled into Cuomo’s recent scandals. 

Bharara brought both of the cases against both Silver and Skelos, one of many similarities between the two trials, which played out concurrently. Each entangled Glenwood Management and ended in years-long appeals that allowed the former Assembly members to avoid their prison sentences. 

Skelos was convicted in 2015 of influencing companies with business before the state to hire his son, Adam, in a series of no-show jobs that netted the younger Skelos $300,000. Glenwood, prosecutors said, was one of three firms the Senator pressured to hire his son, along with an environmental company and medical malpractice insurer. In Glenwood’s case, the U.S. Attorney’s office charged Skelos with repaying the firm by lobbying for legislation and tax abatements that would benefit the company while threatening to punish anyone who challenged him. Glenwood was fined $270,000 by the state’s Joint Commission on Public Ethics for its involvement in the scandals. 

Skelos, 73, won an appeal of his 2015 conviction, was retried in 2018 and sentenced to four years and three months in prison, slightly less than the five years he was given at his 2016 sentencing. His son’s sentence was reduced to four years in the second trial from the six-and-a-half he was initially given. Skelos began his sentence at a federal facility in Otisville in 2019, five years after the initial charges were brought. Silver reported to prison in August 2020. He was furloughed for two days last year early in the pandemic.

Silver spent the final years of his life hoping for leniency. President Donald Trump quashed one of his final chances at early release by refusing to grant clemency to Silver before he left office in 2020. In a rare moment of humility, Silver expressed regret for his actions at his 2018 sentencing.

“The events that are outlined in these trials have brought a great distrust in New York government. I am extremely, extremely remorseful for that,” he told Manhattan Federal Judge Valerie Caproni, who described him as “deeply corrupt.”

Now, with the state’s first female governor in place, Albany political watchers are waiting with bated breath to see if her administration can finally rebuild the trust broken by “three men in a room.” Hochul has made it clear she’s well-aware of the task at hand.

"No one will ever describe my administration as a toxic work environment," Gov. Kathy Hochul said during her first public appearance after Cuomo announced his resignation. “My administration will be fully transparent.”

Correction: This article initially indicated that Sheldon Silver resigned from the Assembly on Jan. 30, 2015.