A Southampton Joy Ride Gone Wrong: The Aftermath of a Tragic Golf Cart Accident

In the quiet opulence of Southampton’s elite neighborhoods, where multi-million dollar estates line pristine beaches and summer nights often blend into carefree memories, one evening in August 2024 took a devastating turn. What began as a casual gathering among friends ended in serious injuries and subsequent legal action that has shed light on the sometimes reckless privilege enjoyed by the children of America’s wealthiest families. At the center of this story is 23-year-old Garrett Huff, the son of hedge fund magnate Craig Huff, who founded the successful private equity firm Reservoir Capital in 1998. The Huff family’s $15 million Southampton estate, with its 10 bedrooms sprawled across 10,000 square feet, became the setting for what plaintiffs describe as a preventable tragedy resulting from a pattern of dangerous behavior that had allegedly gone unchecked for too long.

According to court documents filed in Suffolk County Supreme Court, the evening had proceeded like many summer nights in the Hamptons – with friends Garrett Huff, John Mascali (24), and Heather Dailey spending hours at the beach followed by a game of “wine pong” in the basement of the Huff mansion. As the night progressed and alcohol continued to flow, the trio decided to make one final trip to the beach using the family’s oversized, three-row golf cart. What should have been a short, pleasant ride took a horrific turn when, according to Mascali and Dailey’s accounts, Huff suddenly accelerated without warning. “In no more than 10 seconds the golf cart was at full speed,” Mascali later recalled to The Post. He described the terrifying sensation of feeling “the golf cart lift up off the ground” before everything went dark. The lawsuit alleges that Huff intentionally drove the vehicle at full speed onto a roundabout and attempted “a dangerous stunt which pushed the vehicle to its tipping point,” causing it to overturn and violently throw both passengers to the pavement, rendering them unconscious.

The aftermath of the crash paints a harrowing picture of the injuries sustained by both victims. Mascali, a Sag Harbor native, regained consciousness to find himself suffering from spinal fractures and a concussion. More distressing was the sight that greeted him – his friend Heather Dailey lying motionless with “blood streaming from her skull.” The image haunts him still: “I thought she was likely dead. I just remember collapsing on my knees in front of her.” Both injured friends were rushed to a local hospital where Dailey, a New Jersey resident, required five staples to close the wound on her head. The physical recovery process has been difficult for both victims – Dailey now suffers from debilitating migraines, while Mascali continues to deal with the effects of his spinal injuries. Beyond the physical trauma, both have described the psychological impact of the accident, with Dailey recounting how terrified she felt seeing Mascali motionless on the ground, believing he might have died from the impact.

The lawsuit filed against not only Garrett Huff but also his parents, Craig and Tracey Huff, seeks unspecified damages and makes some particularly damning allegations about the family’s knowledge of their son’s previous behavior. According to the legal documents, the Huffs were well aware that Garrett “had a history of engaging in reckless joyrides” with the golf cart, “especially under the influence of alcohol.” More concerning is the claim that he had “previously injured a friend’s hand in a similar stunt,” suggesting a pattern of dangerous behavior rather than an isolated incident. The plaintiffs’ attorney, William A. Brewer III, emphasized this point, stating: “This was not an accident – it was the predictable result of recklessness and a long-ignored pattern of dangerous behavior.” The suit further alleges that following the incident, the Huff family disposed of the golf cart, potentially removing evidence related to the accident.

The case has drawn attention to the lifestyle of the Huff family, whose wealth allows them to move between luxury properties – including their Southampton estate and an $11 million, 15-room spread on Fifth Avenue directly across from the Metropolitan Museum of Art in Manhattan. Tracey Huff once casually mentioned to The New York Times spending $200,000 on a closet, a comment that now seems particularly tone-deaf in light of the suffering allegedly caused by their son. The stark contrast between the family’s immense privilege and the life-altering injuries sustained by two young people has become a focal point in discussions about accountability among the ultra-wealthy. The allegations suggest that despite having every resource available to address their son’s purported pattern of reckless behavior, the Huffs failed to take appropriate action until it resulted in serious harm to others.

As the legal process unfolds, the case raises important questions about parental responsibility, the culture of excess that can develop around wealth, and the real human cost of what some might dismiss as youthful indiscretions. For Mascali and Dailey, whose lives have been permanently altered by that August evening, justice may come in the form of financial compensation, but the physical and emotional scars will remain long after any settlement is reached. The Huffs have not publicly responded to the allegations, remaining silent in the face of what has become a cautionary tale about privilege without responsibility. Meanwhile, in Southampton and similar enclaves of wealth across America, other families might be taking note – that even in the protective bubble of extreme affluence, actions eventually have consequences, and no amount of money can fully repair the damage done when thrill-seeking turns to tragedy.