Bobby Simone
After the forced retirement of Kelly, Simone becomes Sipowics new detective partner. The two become very close, with Simone even stepping in to be Sipowics’ best man at his wedding (to Sylvia). Simone was previously married before joining the 15th precinct, however his wife Mary dies of cancer. Shortly after having joined the squad, Simone starts a relationship with detective Diane Russell (season 3). Couples who were dating were not allowed to work in the same precinct, so both characters kept their relationship a secret until they got married in season 5. One season later,, Simone undergoes a heart transplant which causes a bacterial infection in his chest, which travels to his brain. Simone dies from this infection, leaving behind a devastated widow, Diane, and partner, Andy.
Maria "Mary" Cimino
Bobby Simone’s first wife, who does not make an appearance on the show. She dies of cancer, leaving Simone a widower before he joins the squad.
Diane Russell
A detective of the 15th precinct who, while working a case with Simone, falls in love and begins a relationship with him. However, the relationship is a tumultuous one; the two break up due to Russell’s alcoholism. Russell struggles with alcoholism throughout her time on the show but is able to reach sobriety with the help of her close friend Sipowics. Russell and Simone eventually rekindle their romance and Russell becomes pregnant, but unfortuantely has a miscarriage. After this, the two get married, however Simone soon dies after this, leaving Russell a widow. After some time, she briefly enters a relationship with Sipowics’ new partner however it does not work out. Russell then takes a leave of absence for some time and, upon her return to work, she begins working with the departements Special Victims unit (for sex based crimes).
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