For 10 years, Jimmy Smits played Detective Bobby Simone, who started off as a driver for the Police Commissioner gets his golden ticket when when Detective Sipowicz’ partner, John Kelly chooses to transfer out of the 15th. Simone learns some hard lessons in the beginning but eventually finds his place, thanks to Sipowicz’ guiding hand, but sadly passes away due to a heart condition the in the sixth season, shortly after marrying fellow officer Diane Russell.