Lawyer caught smooching underling could lose millions, sources say

A married New York City lawyer who was caught kissing an underling on a Central Park bench stands to lose tens of millions of dollars after a rival firm retracted a lucrative job offer, it is claimed. 

Nathaniel D Cullerton, 45, was among six partners at Wachtell, Lipton, Rosen & Katz who were expected to soon jump ship to rival Gibson Dunn.

But his employment offer was reportedly rescinded after he was recorded canoodling in the park with his 29-year-old colleague Kelsey Borenzweig.

Cullerton is estimated to earn a salary of at least $4 million as a junior partner at Wachtell, legal sources told the New York Post.  

Senior partners at the firm are paid around $12 million.

While the exact details of the proposed compensation package from Gibson is confidential, the insiders allege Wachtell would have counter offered with ‘even more’ money to avoid him being poached. He’d likely have earned tens of millions of dollars over the next few decades in his career, had it not been derailed by scandal. 

Cullerton was suspended as Wachtell carries out an investigation into a now-viral video of him and Borenzweig, the Financial Times reported Tuesday.

The loved up pair were caught together in the shadows of Billionaires’ Row by a TikTok comedian named Jay Guapo, who shared the clip with his 3.5 million followers last week. It is unclear when the video was filmed. 

Nathaniel D Cullerton, 45, was filmed smooching Kelsey Borenzweig, 29, by a TikTok comedian. The loved-up couple were quickly identified, and the clip, filmed in Central Park, spread like wildfire across social media, setting elite New York law circles ablaze with gossip

Cullerton, pictured last week, was among six partners at Wachtell, Lipton, Rosen & Katz who were expected to soon jump ship to rival Gibson Dunn. But his employment offer was reportedly rescinded after the video went viral

Dressed in a blue cap and sunglᴀsses on Saturday morning, Borenzweig was spotted stepping out for coffee with her parents in Manhattan

It is unclear whether Borenzweig, an ᴀssociate at the firm, is also under investigation over the video.

As of Wednesday morning, both Cullerton’s and Borenzweig’s attorney profiles were still active on Wachtell’s website.

The pᴀssionate kiss took place on the western edge of Central Park, about 30 blocks south of the co-op Cullerton is listed as living in with wife Moira Penza, 42, along an ultra-exclusive stretch of Manhattan’s Fifth Avenue. 

EXCLUSIVE Married elite NYC lawyer is caught in pᴀssionate tryst with underling near home he shares with wife

Guapo could be seen scolding the pair and hissing: ‘Get a room. There’s kids watching.’

Borenzweig and Cullerton tried to shoo him away and cover his camera on realizing that their tryst was being filmed. He walked towards Guapo and forcefully demanded: ‘Put the phone down,’ but to no avail.

The loved-up couple were quickly identified by commenters when Guapo uploaded the clip to his TikTok. It spread like wildfire across social media and set elite New York City law circles ablaze with gossip. 

It is unclear when Cullerton and Borenzweig’s romance started or whether it had been disclosed to human resources, but the pair worked closely together to win the Altman case against Elon Musk. 

Musk claimed Altman had broken a founding agreement to keep OpenAI a nonprofit. 

A pH๏τo taken during the trial in May 2026 showed Cullerton smiling as he walked into the federal court building in Oakland, California, with Borenzweig just a few steps behind him. 

Cullerton and Borenzweig walking into the Oakland Federal Courthouse in May. They worked together to defeat a civil lawsuit filed by Elon Musk against Sam Altman

Borenzweig works alongside Cullerton in the litigation department of Wachtell, Lipton, Rosen & Katz

Cullerton’s wife Moira Penza is a former federal prosecutor who now works in private practice

EXCLUSIVE Tragic family secret that haunts married lawyer caught on camera kissing underling in Central Park

Cullerton’s wife, Penza, is a partner at another top law firm, Wilkinson Stekloff. 

They married in February 2016. Before moving into private practice, Penza worked as a federal prosecutor and led the case against NXIVM Sєx cult leader Keith Raniere. 

She appeared on an episode of the HBO series The Vow, which investigated the secretive cult.

Cullerton’s meteoric rise to success saw him obtain his JD from Georgetown University in 2013, before clerking at the United States Court of Appeals for the Second Circuit. 

Borenzweig’s legal pedigree is just as impressive. 

She received her JD from New York University School of Law in 2022 and also spent time clerking before joining Wachtell. 

She grew up in Malibu, California, in a sizable $2.7 million midcentury home moments from the Pacific Ocean.

The Daily Mail has approached Wachtell, Lipton, Rosen & Katz for comment.