Ray Machowski is a corrupt police officer in the Liberty City Police Department who works as an insider for the Yakuza. He is introduced to Claude while receiving a payment from Asuka for his previous job with the Yakuza.
Machowski is depicted as heavily cautious with his activities, and is willing to silence associates who attempted to expose any crime committed by either him or his partners. By the end of his presence in Liberty City, the CIA has begun investigating Machowski's links with the Colombian Cartel and the SPANK, forcing Machowski to flee the city and escape to Miami, Florida. In the process of working for Machowski, Claude is introduced to Donald Love, after helping to dispose embarrassing photographs of Love in a "morgue party".
Machowski makes a second appearance in Liberty City Stories, as a partner of Leon McAffrey. The game reveals that Machowski was initially uncomfortable working for criminals and taking bribes, suggesting that he had only turned corrupt recently.
Ray Machowski was voiced by Robert Loggia.