In September 2020, Officer Sylvester was involved in an incident where he allegedly assaulted a man during a confrontation over the mask mandate outside a 7-Eleven in Wahiawa. Body camera footage shows Sylvester forcibly throwing the individual to the ground, leading to serious injuries. A lawsuit was filed against the city, alleging assault, battery, and negligence. Sylvester has been at the center of other high-profile incidents, including a 2016 DUI arrest and the 2021 fatal shooting of Lindani Myeni.