Who Is Nathaniel Cullerton? Married Lawyer Facing Career Ruin After Tiktoker Catches Him Canoodling in Central Park

A single TikTok clip filmed near Billionaires' Row has upended the career of one of New York's most prominent litigators. Nathaniel D. Cullerton, a 45-year-old partner at Wachtell, Lipton, Rosen & Katz, has been placed on leave and lost a lucrative move to rival firm Gibson Dunn after footage showed him kissing a younger colleague on a Central Park bench.

The video, filmed by comedian Jay Guapo and viewed more than four million times, has thrust Cullerton's personal life into public view just months after he helped win one of the year's most closely watched corporate lawsuits.

Courtroom Victory To Viral Scandal

Cullerton built his reputation on the biggest legal battle of the year. He was part of the Wachtell legal team that successfully defended OpenAI against Elon Musk's lawsuit, seeking $150 billion in damages.

A photograph taken during the trial in Oakland, California, in May 2026 showed Cullerton smiling as he walked into the federal courthouse.

The defence was led by trial lawyer Bill Savitt, described as the 'mastermind' behind the victory, who was subsequently recruited by Gibson Dunn along with several senior colleagues. Cullerton was understood to be set to follow him, according to the Financial Times.

Nathaniel D. Cullerton earned his JD from Georgetown University in 2013 before clerking at the United States Court of Appeals for the Second Circuit and joining Wachtell.

The Four Million-View Central Park Clip

Cullerton and Kelsey Borenzweig, 29, were caught together in the shadows of Billionaires' Row by TikTok comedian Jay Guapo, who shared the clip with his 3.5 million followers. In the footage, Guapo approaches the pair, and Cullerton turns toward the camera with a confused smile while Borenzweig appears equally caught off guard; the two then ask him to stop filming, a request he ignores.

It remains unclear exactly when the video was filmed or whether the relationship had been disclosed to the firm's human resources department.

The professional stakes were immediate. Cullerton's planned lateral move to Gibson Dunn was scrapped in the wake of the video, according to a report in the Financial Times, which cited sources familiar with the matter. The controversy has led Gibson Dunn to withdraw its offer to Cullerton, who was earning at least £3.1 million ($4 million) annually as a junior partner at Wachtell, according to industry sources.

A Marriage, a Firm Investigation and Millions on the Line

Cullerton's personal life adds another layer to the story. He is married to Moira Penza, a former federal prosecutor who led the case against NXIVM sex cult leader Keith Raniere and later appeared on the HBO series 'The Vow.' Penza, now a partner at Wilkinson Stekloff, married Cullerton in February 2016.

Cullerton has been placed on leave, according to a report in the Financial Times, which cited sources familiar with the matter. Wachtell has not responded to requests for comment on whether Cullerton is under internal investigation.

Because Cullerton held direct authority over associates in his department, including their assignments, evaluations, and career trajectories, the partner-associate dynamic between him and Borenzweig has raised scrutiny that extends beyond questions of personal judgement.

The financial fallout could be severe. Legal industry recruiters have suggested the collapse of his move to Gibson Dunn could cost Cullerton tens of millions of dollars over the course of his career. Wachtell, Lipton, Rosen & Katz is known as a firm where partners rarely find themselves at the centre of public controversy, making the fallout especially conspicuous within elite legal circles.

It is unclear whether Borenzweig, as an associate, is also subject to internal scrutiny. She has not publicly commented.

For a lawyer who spent months in the national spotlight defending one of Silicon Valley's most valuable companies, Nathaniel Cullerton now finds his own reputation on trial in the court of public opinion.