Singletary grew up in the 19th Ward neighborhood of Rochester, and wanted to become a police officer from a young age.

Prude was under the influence of Angel Dust and was walking the city streets naked before being physically restrained by the police.

The incident gained nationwide attention, and after public pressure and a city council investigation that determined that Mayor Lovely Warren and Singletary concealed critical details about Prude's death from the public and lied about their knowledge of the case,[3] Singletary and all other members of the Rochester Police Department command staff resigned.

[5] In December 2020, Singletary accused Rochester mayor Lovely Warren of pressuring him to lie about the series of events following the death of Daniel Prude and firing him after he refused.

[6] He later filed a successful lawsuit against the city asking for medical benefits promised to employees who work in the department for more than 20 years.