Andrew Cuomo and Jeanine Pirro have a contentious past. Now his fate may rest with her.

Gov. Andrew Cuomo has a long, combative history with Jeanine Pirro, the federal prosecutor in Washington, D.C. who is reportedly overseeing a criminal investigation against him.

The New York Times first broke the news of the investigation Tuesday night. The paper reported that the U.S. attorney’s office for the District of Columbia is investigating comments Cuomo made to Congress last year about his management of the COVID-19 pandemic.

The news comes just weeks before the June primary in the New York City mayoral race, where Cuomo is a front-runner. Cuomo’s spokesperson said in a statement that the investigation is politically motivated.

But almost 20 years ago, on the threshold of a different election, it was Pirro who found herself facing a criminal investigation. That was in 2006, when Pirro was the Republican candidate for New York attorney general. In that case, her Democratic opponent was none other than Andrew Cuomo. And while prosecutors never brought charges against Pirro, Cuomo used the investigation as fodder to undermine Pirro’s campaign.

The reported investigation into Cuomo has been ongoing for about a month, according to the Times. That means it predates Pirro’s appointment. Nonetheless, his fate could now rest in his former opponent’s hands.

Campaign rivalry boils over in heated 2006 campaign debate

Weeks before Election Day that year, reports emerged that federal prosecutors were investigating Pirro, a former judge and Westchester County district attorney, on allegations that she asked former NYPD Commissioner Bernard Kerik to secretly record her husband, who she believed might be having an affair.

“There is a candidate who is being accused of criminal wrongdoing and is under investigation by a number of law enforcement agencies and has their ethics questioned. That’s not me, however,” Cuomo said at a campaign debate in October 2006.

Pirro insisted at the debate that she hadn’t done anything wrong. She said the issue was a “personal matter” that shouldn’t factor into the election.

“ People understand that the leaking of this information 40 days before an election was timed to hurt me personally and to hurt my campaign,” she said.

Cuomo and Pirro didn’t just spar about the criminal investigation. Throughout the debate, the two disputed each others’ records and clashed on policy issues, from immigration and gay marriage to the death penalty. Pirro accused Cuomo of “hypocrisy upon hypocrisy” when he promised to clean up government corruption in Albany. Cuomo accused Pirro of “sensationalizing” and “changing facts” to fit her arguments.

Pirro also repeatedly criticized Cuomo for not doing enough to protect victims of sexual abuse, like she said she had as a prosecutor. She questioned why he hadn’t advocated for legislation that would allow for the civil confinement of people who repeatedly molest women and children, which she said had been languishing in Albany for years. Cuomo responded that “ there will not be an attorney general who will do more to protect children from sexual predators than me.”

Cuomo won that election and later went on to become governor. He resigned in 2021 after Attorney General Letitia James found that he had sexually harassed multiple women, including staff members.

Pirro moves to Fox News — and uses her platform to call out Cuomo

Pirro later pivoted to a career in cable news. On her former Fox News show "Justice with Judge Jeanine," Pirro dedicated an entire monologue in 2021 to the same topic that’s reportedly at the center of the new investigation: Cuomo’s handling of the COVID-19 pandemic in nursing homes.

“ The reason Americans don't trust politicians is because they lie. New York Gov. Andrew Cuomo is a case in point,” she said.

Pirro’s monologue came amid public outcry about a report from the attorney general’s office that found the state was undercounting the number of COVID deaths in nursing homes by omitting many cases when residents died in hospitals. She chided the Cuomo administration’s directive to let nursing home residents return after a hospital stay even if they had COVID, which she said endangered vulnerable seniors. She also condemned legislation he signed that prevented people whose loved ones died in nursing homes and hospitals during the pandemic from filing lawsuits.

“Aren’t you interested in justice? Why do you prefer to block justice?” she asked rhetorically, staring straight into the camera. “So now the question is, will the attorney general, who has jurisdiction over crimes, refer your malfeasance to the deputy attorney general for a grand jury investigation?”

Pirro called Cuomo’s actions “gruesome,” “incompetent” and a “criminal scheme.” She questioned whether the governor could be charged with manslaughter or criminally negligent homicide.

Cuomo has denied wrongdoing when he testified before a House subcommittee last year. He said he hadn’t reviewed the directive about admitting COVID-positive patients to nursing homes before it was issued and learned about its existence about a month later, according to a transcript of his testimony. He also said that reporting COVID deaths accurately “was of paramount importance” to him. The subcommittee accused Cuomo of lying to Congress and asked the Department of Justice to investigate him.

Pirro’s power over Cuomo in the Trump administration

Pirro now leads the office that’s reportedly investigating her former political foe. Earlier this month, Trump selected Pirro to be the interim U.S. attorney in Washington after his first choice, Ed Martin Jr., failed to garner enough congressional support.

“Jeanine is incredibly well qualified for this position, and is considered one of the Top District Attorneys in the History of the State of New York,” Trump said in a Truth Social post announcing her appointment. “She is in a class by herself.”

Pirro’s ex-husband, Albert Pirro Jr., was the last person Trump pardoned before leaving office in 2021. He was convicted on federal fraud and tax evasion charges in 2000.

The Department of Justice has not publicly confirmed the investigation into Cuomo, and a spokesperson did not immediately respond to questions about why it might be pursuing an inquiry in the midst of a mayoral campaign. Earlier this year, the Department of Justice pressured prosecutors in New York City to dismiss an indictment against Mayor Eric Adams, partly because officials said it came too close to the election.