Family secret that haunts married NYC lawyer caught kissing underling

The cheating New York City lawyer busted canoodling with a co-worker on a Central Park bench was left reeling from a family tragedy following the sudden death of his younger brother nearly two decades ago, the Daily Mail has learned. 

Nathaniel D Cullerton’s sibling, Eric Cullerton, was just 24 years of age when he was involved in a ᴅᴇᴀᴅly head-on crash near the family’s home in Connecticut back in 2007. 

Eric had just finished a morning shift at Starbucks in the town of Ridgefield when his 1990 Nissan Sentra crossed into incoming traffic and collided with a Jeep, local reports said. 

At the time, a grief-stricken Cullerton, then aged 26, was among those who paid tribute to his brother, describing him as an incredibly gifted young musician.

‘Eric played in a lot of local bands, blues and rock,’ Cullerton told The News-Times shortly after the tragedy.

‘He toured the US with the Murali Coryell Band for the last year and a half. He had recorded and produced a couple of solo albums. He wrote (music) all the time.’

An obituary in the local paper, too, described his musical talents, noting he would travel with a ‘small cᴀssette recorder everywhere he went to record his ideas and songs.’

‘Eric loved his family. He loved France, where he spent every summer with his cousins and grandparents on his mother’s side.

Nathaniel D Cullerton, 45, was filmed smooching Kelsey Borenzweig, 29, by a TikTok comedian. The loved-up couple were quickly identified when the clip spread like wildfire across social media

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

‘He loved music and lived through it. He was an artist with the gentlest soul. He felt all the pain that is in this world, but also saw and rejoiced in all its beauty.

‘He was deeply loved by all who met him. In the words of a dear family friend, “He moved through life a head taller and several times more humorous and contemplative and kindly than almost every one else, making music and friends wherever he went”.’

The harrowing details of the dark family tragedy surfaced soon after Cullerton, a partner at Wachtell, Lipton, Rosen & Katz, became embroiled in a public scandal in wake of his dalliance with a much younger co-worker. 

The high-flying lawyer was recently caught-on-camera smooching Kelsey Borenzweig, 29, near the luxury $2.3 million apartment he shares with his attorney wife. 

The tryst was exposed when a TikTok comedian named Jay Guapo shared the footage of them French kissing with his 3.5 million followers last Thursday.

At one point, Guapo could be heard telling the lovers to ‘get a room’ before a shame-faced Cullerton tried to shoo him away and order him to stop recording them. 

The clip quickly spread like wildfire on social media as online sleuths outed the sheepish lovers as Cullerton and Borenzweig. 

The pair both work within the law firm’s litigation department.

A grief-stricken Cullerton was among those who paid tribute to his brother, describing him in a local news article as an incredibly gifted young musician

Cullerton, who has been married to his wife Moira Penza since 2016, looked sheepish as he was spotted in Manhattan on Friday after news of the scandal started going viral

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

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

This spring, the firm helped OpenAI boss Sam Altman defeat a civil lawsuit brought by Elon Musk. 

Neither Cullerton nor Borenzweig have addressed the viral controversy. 

Cullerton, for his part, has been married to Moira Penza, a 42-year-old partner at another top law firm, Wilkinson Stekloff, since 2026.

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

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

Penza has been тιԍнт-lipped in the wake of the cheating scandal. 

Her sheepish husband was spotted looking stressed as he broke cover late last week traveling back-and-forth between his Manhattan digs and the couple’s home in Connecticut, where he is originally from.

He was seen arriving at the $1.4 million second home he owns with Penza in Wilton before heading back to the Upper East Side in his luxe Range Rover. 

He ignored a Daily Mail reporter’s questions about whether his wife had seen the clip.  

Borenzweig, meanwhile, was snapped with her parents in Manhattan soon after news of the scandal broke. 

The ᴀssociate was most recently in a relationship with a fellow lawyer but the romance ended a few months ago, a source told the Daily Mail. 

It is unclear how long Cullerton and Borenzweig have been romantically linked.   

The Daily Mail has repeatedly contacted Wachtell, Lipton, Rosen & Katz for comment on Cullerton and Borenzweig’s relationship but hasn’t received a response. 

Cullerton’s wife Moira Penza is a former federal prosecutor who now works in private practice. Penza appeared on an episode of HBO series The Vow, which investigated the NXIVM Sєx cult

The high-flying lawyer was recently caught-on-camera smooching Kelsey Borenzweig, 29, (pictured above) near the luxury $2.3 million apartment he shares with his attorney wife 

Cullerton was spotted looking stressed as he broke cover traveling back-and-forth between his Manhattan digs and the couple’s home in Connecticut

Cullerton, wearing a rumpled linen shirt, ignored questions from a Daily Mail reporter about the video of him kissing an underling and instead kept his phone pressed to his ear as he walked into his apartment over the weekend

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

The pair worked closely together to win the Altman case against Elon Musk.

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

Cullerton’s meteoric rise to success saw him obtain his Juris Doctor (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 pair’s kiss has drawn comparisons online to an infamous clinch caught on a kiss cam at a Coldplay concert near Boston last summer when Andy Byron, then CEO of data software firm Astronomer, was filmed cuddling the firm’s HR executive Kristin Cabot.