Andrew Cuomo's Infamous Opsec Avoids Paper Trails. Will It Be Enough?

A few short months after his reign as a national media darling, New York Gov. Andrew Cuomo now finds himself at the center of a swirl of investigations. The scandals revolve around his administration’s efforts to conceal the death toll resulting from a decision to send coronavirus-infected older adults back to nursing homes and a growing number of accusations that the governor’s cultivated atmosphere of bullying and performative dominance included his own sexual harassment and assault of women who worked for him.

As inquiries by the State Assembly, New York’s attorney general, and the U.S. Justice Department get underway, investigators are likely to encounter the same obstacle that complicated previous investigations into Cuomo’s inner circle: a scrupulously observed protocol of information security. This modus operandi has allowed the governor to wheedle, threaten, cajole, and otherwise operate the levers of power while leaving hardly any public record of his involvement.

For more than a decade, Cuomo has adhered to the maxim of his predecessor, Eliot Spitzer, who counseled: “Never write when you can talk. Never talk when you can nod. And never put anything in an email.” So it is that well into the 21st century, Cuomo claims not to be comfortable with email, instead receiving information and relaying instructions through his lieutenants or, when necessary, by telephone.

Cuomo is neither the first nor the only powerful politician to rely on such infosec to thwart attempts at accountability, but he has made an art form out of it. When a researcher filed a Freedom of Information request in December 2018 for the most recent 200 pages of emails sent to, from, or copied to Cuomo, the governor’s office answered that it had no responsive records. “I don’t want to say that I’m a sort of old-fashioned, telephone guy, but a little bit I am,” Cuomo said, explaining his email avoidance with what the Journal News described as “a smirk.”

“Not using email has some big disadvantages in a world where that’s the way everyone else around you is communicating,” said John Kaehny, executive director of Reinvent Albany, a good-government group that advocates for transparency from New York’s public officials. “But it has one big advantage: if you’re under investigation, because there’s much less of a written record. What seems to have been the practice with Cuomo, throughout his administration, is that his aides use email, and then they talk to him in a way that doesn’t generate discoverable records.”

“Not using email has some big disadvantages in a world where that’s the way everyone else around you is communicating. But it has one big advantage: if you’re under investigation.”

Previous investigations into corruption in the Cuomo administration have reached all the way up to his inner circle, but publicly available records of those investigations show no indication that prosecutors ever found electronic records linked to the governor himself. Prosecutors never charged Cuomo with directing the corrupt activities of his top aides, some of whom were sentenced to years in federal prison.

The current investigations are different from those that came before. The nursing home scandal concerns not just ordinary corruption but the attempted cover-up of thousands of deaths. And the sheer number — eight as of the publication of this story — of people accusing Cuomo of personally sexual harassing or assaulting them makes that scandal markedly different from those that the governor has skated by in the past. The accumulation of scandals has also meant the collapse of a key pillar of Cuomo’s infosec regime: It always relied on fear to keep people who were privy to the conversations — but never emails — from talking, but with each new public allegation, more witnesses seem emboldened to come forward.

Will these differences overcome the layers of insulation that have protected the governor until now? “That’s the outstanding question,” Kaehny told The Intercept. “We’re about to find out.”

New York State Governor Eliot Spitzer speaks as Andrew Cuomo, New York State Attorney General looks on during a news conference to introduce initiatives to address irresponsible home lending practices in New York. (Photo by Ramin Talaie/Corbis via Getty Images)

New York Gov. Eliot Spitzer speaks as Andrew Cuomo, New York attorney general, looks on during a news conference in New York on Nov. 8, 2007.

Photo: Ramin Talaie/Corbis via Getty Images

Political scandal has attached itself to Cuomo from the very earliest days of his political career. As a young enforcer in his father’s failed mayoral campaign, Andy, as he was then known, was widely suspected of being the author of posters urging Queens residents to “Vote for Cuomo, not the homo.” Ed Koch, the target of the ads, came to believe that Andrew was responsible. Cuomo has denied it, and it never hampered his career, in which he was elevated to a cabinet secretary position in President Bill Clinton’s administration and, finally, elected governor of New York in 2010.

In a few short years, scandal would catch up with Cuomo in Albany — and his ruthless control of information would begin to emerge. In 2014, he unilaterally shuttered the state’s months-old anti-corruption commission after it had begun to look into his own donors. Reports emerged that Cuomo’s team had meddled in the investigation, drawing the attention of the news media and a federal prosecutor. A top Cuomo aide, Joseph Percoco, performed damage control behind the scenes, urging members of the now-defunct panel to defend its erstwhile independence from the man who had just hobbled and ultimately killed it. Percoco reportedly encouraged the members to discuss the matter with him using private email accounts — not government accounts that would be harder to conceal from Freedom of Information Law disclosure.

Using private email accounts for government business is expressly prohibited by New York state government’s technology policy, and Cuomo’s team repeatedly denied that his staff used private email accounts in service of the governor. It was a remarkable position to stake out because lots of people, including the reporters to whom they were issuing the denials, had received official email correspondence from the personal accounts of Cuomo aides.

Cuomo’s alleged unease with modern technology didn’t prevent him from communicating for years using a private BlackBerry messaging system that leaves no electronic record.

Significantly, Cuomo’s alleged unease with modern technology didn’t prevent him from communicating for years using a private BlackBerry messaging system that leaves no electronic record. His preoccupation with scrubbing the record extends in other directions as well: Cuomo also instituted a new regulation requiring state agencies to automatically destroy their email records after 90 days.

The firewall erected around the governor by top lieutenants has always held strong. When Percoco, whom Cuomo had described as his father’s “third son,” was convicted in a massive bribery scandal, federal investigators were unable to prove that the governor, whose obsessively controlling style of micromanagement is renowned, had any idea what his right-hand man was doing. Similarly, when Cuomo’s signature “Buffalo Billion” initiative dissolved into a sludgy morass of bid-rigging and corruption, the judge sentencing Alain Kaloyeros, Cuomo’s intermediary on the project, concluded that he steered lucrative contracts to Cuomo’s donors out of a “desire to earn brownie points with the Executive Chamber” and sentenced him to three years in prison. It may stretch belief that Kaloyeros would risk prison to impress Cuomo with a corrupt scheme that Cuomo had no knowledge of, but prosecutors found no concrete evidence to show that the governor knew what was going on.

These scandals singed Cuomo but did not burn him, at least among New York voters, long accustomed to murky doings in their state government. In 2018, Cuomo won a third term, and as the Covid-19 pandemic raged across the state and the country in 2020, he leveraged low-information viewers’ fearful longing for a reassuring strongman to gain national acclaim with high-profile televised briefings.

NEW YORK, NY - MARCH 20: Former New York Governor Andrew Cuomo aide Lindsey Boylan and dozens of protesters gather at Washington Square Park to demand the governors resignation on March 20, 2021 in New York City. The demands for Governor Cuomos resignation are in response to the sexual harassment allegations made by numerous women and a cover-up preventable of coronavirus (COVID-19) deaths in nursing homes. (Photo by David Dee Delgado/Getty Images)

Former Cuomo aide Lindsey Boylan and dozens of protesters gather at Washington Square Park to demand the governor’s resignation in New York on March 20, 2021.

Photo: David Dee Delgado/Getty Images

Now, as the twin scandals engulfing the Cuomo administration develop, the hermetic infosec regime of his executive chamber is once again coming into play. Both scandals — the allegations of sexual misconduct and the altering of a report to conceal the number of nursing home Covid-19 deaths — are rooted in a similar action: Someone asked for something inappropriate. In the nursing home scandal, it was a change in reporting data; in the sexual misconduct one, it was submission and acquiescence. The question investigators in both cases are now seeking to answer is: Who directed those inappropriate requests?

As investigators follow the emails and communications up the chain of command, it appears likely that they will arrive where previous investigators have: at the feet of loyal aides in Cuomo’s inner circle but with no documentary proof linking the air-gapped governor to the misdeeds of his team. Whether investigators can prove Cuomo’s responsibility will depend on what his most loyal aides choose to say.

When Lindsey Boylan, the first woman to level sexual assault and harassment claims against Cuomo, specified her allegations in a Medium post in February, she included a receipt: an email telling her that she looked like Cuomo’s rumored ex-girlfriend, only even more attractive. The email didn’t come from Cuomo, but rather from Stephanie Benton, director of the governor’s offices, dutifully relaying her boss’s clumsy come-ons. “He said look up Lisa Shields,” the screenshotted email said. “You could be sisters. Except you’re the better looking sister.”

Whether investigators can prove Cuomo’s responsibility will depend on what his most loyal aides choose to say.

It may be that, as Benton now claims, the wildly inappropriate message was sent on her own initiative, that when she wrote that Cuomo was directing Boylan to look up photographs of a woman said to be his ex-girlfriend, he actually hadn’t, and Benton was inventing this instruction as an “attempt at banter.” Alternatively, it could be that Benton’s willingness to take responsibility, even with such an improbable explanation, speaks to the determination of Cuomo’s inner circle to fall on their swords to protect him from the consequences of his actions.

The Cuomo administration’s strategic relationship to public records also resurfaced in the scandal. When digging up records serves Cuomo’s interests, they come readily to hand. His government claimed in 2014 that it had no records of the governor’s travel expenses for his first three years in office, but it swiftly scrounged up flight manifests this spring in an effort to rebut reports that the governor sexually harassed Boylan on a shared flight. Weaponizing public records further, after Boylan’s claims gained media attention, team Cuomo released human resources records depicting her as a bad boss.

With the demise of BlackBerry and its recordless messaging app, Cuomo has gotten himself an iPhone. Even here we learn that Cuomo found a way to use his performative tech-illiteracy for sinister ends: According to allegations first reported in the Times Union, at least two of the women whom Cuomo subjected to inappropriate intimacy were lured into his presence on the pretext of helping him figure out how to work his phone. A lawyer for Charlotte Bennett, a former aide, alleges that she was summoned to the governor’s private residence because he claimed that he “was uncertain how to get from his ‘settings’ app to his ‘notes’ app.” Another woman alleges that she was summoned to the residence five months later because “Cuomo said he could not operate the ‘notes’ app on his iPhone and needed her assistance,” only to have the governor use the opportunity to reach up her shirt and grope her breasts.

Cuomo’s communications practices make it difficult to disprove his own version of events. There is presumably no record to prove that he dictated the weird ex-girlfriend text that Benton sent to Boylan. Democratic State Assembly Member Ron Kim, who said Cuomo called him out of the blue late at night with instructions to stop making trouble about the nursing home scandal, has not suggested that he has any recording to prove Cuomo threatened to destroy him. In criminal prosecutions and other formal investigations, an unlikely explanation may suffice if there isn’t concrete evidence to contradict it.

There’s a way in which the sheer implausibility of the premises of Cuomo’s dodges — consider a grown man repeatedly calling aides for help opening his Notes app — are themselves a sort of flex. Cuomo is showing these women that he doesn’t need a plausible excuse to bring their bodies close to him, because he’s Cuomo. It’s these gravity-defying claims, daring you to be so foolish as to challenge them and risk destruction, that are the true hallmark of the Cuomo administration.

Does he care if you believe that he invented the “Women’s Equality Party” out of a true-born upwelling of feminist sentiment? Does he care if you believe that he was helpless to prevent years of Republican control of the Legislature, rather than encouraging it to service his personal ambitions? He does not.

As journalist Masha Gessen, writing about President Donald Trump, another son of Queens, pointed out in their book “Surviving Autocracy,” there is a category of lie not intended to persuade or deceive. “It is the power lie, or the bully lie,” they wrote. “It is the lie of the bigger kid who took your hat and is wearing it—while denying that he took it. There is no defense against this lie because the point of the lie is to assert power, to show ‘I can say what I want when I want to.’”

There’s reason to wonder whether Cuomo’s meticulous insulation will get him off the hook this time. As the public has grown accustomed in recent years to evaluating allegations of sexual misconduct, the coordinated denials of disciplined loyalists and the absence of a conclusive paper trail to support the allegations may matter less than the number and credibility of the accusers.

As the wall of omertà crumbles, others who have bitten their tongues until now are sharing their experience of Cuomo. Kim and Boylan seem to have broken the dam — with new revelations showing that, until recently, even Cuomo’s antagonists have felt the need to hold back.

Take, for example, a three-year-old story that resurfaced this winter. The governor’s hostile relationship with the Working Families Party is the stuff of legend and his fury at the left-leaning third party for failing to enthusiastically support him has long been known. In February, someone told the New York Times about a 2018 attempt by Cuomo to bully WFP leaders over the party’s lukewarm endorsement. The paper quoted Cuomo saying, “If you ever say, ‘Well he’s better than a Republican’ again, then I’m going to say, ‘You’re better than a child rapist.’ How about that?” The governor denied the allegation. This month, the Times put the lie to Cuomo’s denial, releasing a recording of the call — the sort of leak that was unthinkable last year for fear of how Cuomo would react.

The bully’s lie is premised on a fearful audience, and as The Intercept has reported, politics in Albany has shifted. The people who hold Cuomo’s fate in their hands are less fearful than they once were. The recent memory of Trump has left Americans with a bad taste for a politics of bullying. With these shifts, and with each act of defiance, small and large, the impunity that Cuomo’s communication firewall has previously bought him is increasingly undermined.

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