In the village of Briarcliff Manor, a tony suburb outside New York City, everybody knew Clay Tiffany. Growing up in the 1960s, Tiffany was a Briarcliff Manor High School basketball legend; his name is still etched on a plaque in the trophy case that commemorates the school’s thousand-point scorers. By the time I met Tiffany, in 2002, he was in his fifties, and Briarcliff Manor residents knew him as the village gadfly.
Over six feet tall, white, and with an unruly crown of curly red hair, Clay Tiffany spent his days as a self-proclaimed independent journalist, uncovering local practices he considered unfair or unlawful and complaining about them to local officials and at village council meetings. Tiffany also shared the fruits of his investigative labor on his remarkably named public access television show, Dirge for the Charlatans.
On a March afternoon in 1997, Tiffany was pulled over by a Briarcliff Manor police officer he did not recognize. The officer, Nick Tartaglione, had recently been hired by the department. With bulging muscles and a deep tan, Tartaglione stuck out as much as Tiffany did in Briarcliff Manor. According to Tiffany, Tartaglione approached his car and said, through the open window, that he heard Tiffany like moulinyans—derogatory Italian slang for Black people—and then said, “I’m connected with the Mob. I can have you taken care of any time I want.” Feeling threatened, Tiffany got out of his car and, standing several feet away, said that he was afraid of Tartaglione and was going to flag down the next car he saw and give the driver the name of a friend to call. When Tiffany got a car to stop and started speaking with the driver, Officer Tartaglione grabbed Tiffany, slammed him into the police car, and handcuffed him.
Tiffany quickly turned his investigative attentions to Tartaglione. And it turned out there was a lot to investigate. Tiffany learned that Tartaglione had beaten up people while employed as an officer in neighboring jurisdictions, and had left those jobs under suspicious circumstances. Tiffany then started reporting what he found out about Tartaglione on Dirge for the Charlatans. That apparently got under Tartaglione’s skin.
Over the next two and a half years, Officer Tartaglione assaulted Tiffany three more times—the assaults growing more extreme with every encounter. The final time, Tartaglione maced Tiffany, and punched and kicked him, yelling “You can’t tell lies about me on your television show!” Officer Tartaglione broke Tiffany’s orbital bone and several ribs, landing him in the hospital.
Tiffany sued Tartaglione and the Village of Briarcliff Manor. During litigation, Tartaglione offered to settle the claims against him for $200,000. Soon thereafter, we wrote a letter to defense counsel, explaining that Tiffany wanted to know where the money was coming from—Tartaglione himself, or the village. I assumed the money was coming from Tartaglione; the village had fired Tartaglione and was arguing during litigation that his assaults of Tiffany were outside the scope of his employment. But in the end, after Tiffany had accepted the money, Briarcliff Manor revealed that its insurer had written the check. I was shocked. Why would Briarcliff Manor’s insurer pay six figures to settle a case against an officer they had fired? Why would Briarcliff Manor’s insurer pay to settle a case against an officer they argued was acting outside the scope of their employment? Chapter 10 of SHIELDED helps explain why.