Paramedic Roberto "Bobby" Caffey worked for the FDNY. He was portrayed by Bobby Cannavale and last from season one to season two.
Bobby was born in 1973 or 1974. His father left the family when he was a youngster and died many years later. The relationship did not really recover. Bobby was devoted to his family: his mother, three sisters and older brother Matteo (or "Matty"). Matty fell into using drugs, so despite being the younger of the 2 Caffey brothers, Bobby became the "man of the family". Bobby always thought it was his fault that his father left. His mother later remarried and the whole family adopted the last name "Caffey".
His best friend was Paulie Fuentes, who would go on to play a major role in Bobby's life in the future. Bobby credited his high school geometry teacher, Mrs Bradley, with saving him from going down the same route as Matty and Paulie. Later in life he repaid the debt by helping euthanise her to die peacefully.
Bobby was a paramedic, working at the firehouse in the 55th Precinct. Bobby had been a paramedic for a number of years, working with Kim Zambrano for the past 6 years. Bobby had had a crush on Kim since the day they met. When he finally revealed his feelings for Kim, she turned him down, saying he was too good for her and she'd let him down in the end. They did have a one night stand, which resulted in Kim dumping Bobby. However, the two did recover from this and remained friends. Bobby got on well with Kim's son Joey, and adopted the role of a second father to him. Bobby also had to regularly put up with Kim's rants about her ex-husband, firefighter Jimmy Doherty, who in many ways was Bobby's rival. Bobby also had a short relationship with Dana Murphy, an ER nurse from Angel of Mercy Hospital, and firefighter Alex Taylor.
Bobby was seen as one of the nicest guys around, often helping out anyone in need no matter what the situation. A 13 year old girl named Sunny was being pimped out, and both Bobby and Kim tried to help her out. Sunny stole Kim's wallet in return, causing Bobby to go and get the wallet back from her - and giving her pimp a bruising at the same time. Bobby also secretly replaced the $200 which Sunny had stolen from Kim, which happened to be half of ex-husband Jimmy's child support money. Unfortunately, Sunny died some time later.
Bobby tried to help his brother Matty out numerous times. In 2000 Matty was released from jail, and due to Mrs. Caffey wanting nothing to do with him, he ended up staying with Bobby. Bobby always forgave him for his deceptions and betrayals, which included having an affair with one of Bobby's girlfriends, Serena Cadiz, stealing a large amount of money Bobby had put aside to lend his mother, and stealing Bobby's Ford Mustang. When Matty was involved in a store robbery which ended up with the cashier getting killed, Bobby gave Matty $500 and told Matty that if he took the money, he didn't want to ever hear from him again. Matty would be dead to him. But if he turned himself in, Bobby would do everything he could to make sure Matty didn't do time. He'd wait for his brother until he was let out. Matty decided not to turn himself in, breaking Bobby's heart. It was this incident that led to Bobby and Kim's one night stand.
Bobby met his end near the end of the second season. An old girlfriend of his, Gina (whom Bobby had lost his virginity to many years earlier) came to him asking for him to help out her brother, Paulie - Bobby's childhood friend. Paulie was involved with drugs, and when Bobby had seen Paulie after a number of years, Paulie was passed out. Perhaps feeling guilty after failing to help his brother, Bobby took Paulie to the hospital and offered Paulie the chance of entering rehab. Paulie denied this offer. Later that night, Paulie went by Bobby's, feeling sick. Bobby helped his friend on the condition that Paulie enter rehab. The next day, Bobby got the call that his mom's apartment had been robbed. When he found out Paulie had been the one to rob his mom's house, he went into a fury and went to Paulie's place where he confronted Paulie. Bobby threw Paulie's stash of drugs into a toilet, but ended up getting shot in the heart by Paulie and later died. After his death, Kim, overcome with grief, attempted suicide by overdosing on pills and alcohol in the bath.
Mrs. Caffey (mother)
Mr. Caffey (stepfather)
Matteo "Matty" Caffey (brother)
Renee Caffey (sister)
Jenny Caffey (sister)
Lisa Caffey (sister)
Renee's son (nephew)
Paramedic Kimberly "Kim" Zambrano (best friend - one night stand)