November 24, 2025
Two New Haven officers receive suspended sentences and $15 court fees as Randy Cox, now permanently paralyzed, continues to seek accountability in a case compared to a modern-day “rough ride.”
A Connecticut case that drew national outrage for its striking similarities to the police “rough ride” that killed Freddie Gray, continues to stir anger after two New Haven officers avoided jail time for their roles in paralyzing 36-year-old Randy Cox during a 2022 arrest.
Randy Cox was left permanently paralyzed from the neck down after officers handcuffed him, placed him unrestrained in the back of a police transport van, and then came to a sudden stop that threw him headfirst into a metal divider. The incident ultimately resulted in a $45 million civil settlement, the largest police misconduct payout in U.S. history, according to New Haven Independent.
But this month, two of the officers involved — Ronald Pressley and Betsy Segui — accepted plea deals that amounted to suspended six-month sentences and just $15 in court costs. Neither will serve jail time. Three other officers, including the driver, declined their plea offers and are preparing to go to trial on misdemeanor reckless endangerment and cruelty to persons charges. Lawyers for Cox criticized the modest charges last year as a “slap in the face.”
Officer Oscar Diaz, the van driver, has remained central to the controversy. Diaz claimed he braked suddenly to avoid a collision — but investigators found he was traveling 11 mph over the speed limit. After firing Diaz in 2023, New Haven police were forced to reinstate him with back pay when a state arbitration board determined he wasn’t responsible for Cox’s paralysis. Records show Diaz earned $142,766 in 2022 and more than $210,000 the year before, meaning his back-pay award likely approached $200,000.
“He was an exemplary officer prior to that incident, and we’re going to do everything possible to bring him back,” Police Chief Karl Jacobson said at the time.
Cox’s life, however, has been irreversibly altered. Arrested on weapons-related accusations in New Haven that were later dismissed, he repeatedly begged for help after being thrown across the van.
“I can’t move,” he told Diaz, who responded, “You’re on the side, get up.” When Cox insisted, “I literally can’t move… I think I broke my neck, yo,” officers dismissed him, accusing him of drunkenness.
Instead of calling an ambulance to the scene, Diaz drove past two hospitals to meet paramedics at the station. Once there, officers dragged Cox from the van, placed him in a wheelchair, and then dragged him again when he collapsed — actions that investigators say worsened his spinal injury.
“You ask yourself, was it cruel and unusual punishment to put him in the back of that police transportation van with no seat belt… knowing that if you slam on the brakes that somebody is going to be seriously injured?” attorney Ben Crump said in 2022, calling it a modern-day “rough ride.”
Crump later added, “You cannot just have deliberate indifference when it comes to Black people because you think they’re irrelevant… thank God the video caught how you really felt about Randy Cox.”
Crump compared the encounter to a “rough ride,” a term used to describe when officers transport handcuffed, unrestrained detainees in a deliberately erratic manner — the same practice linked to Freddie Gray’s death in Baltimore in 2015.
Cox, now 39, remains paralyzed, while legal proceedings for the remaining officers continue.
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