Gary had a tortured relationship with his father, who was an alcoholic. His father was killed by Cameron.
His mother (maiden name Armstrong) died after many years of blaming herself for her husband's failures.
Gary had a very antagonistic relationship with his brother Cameron (younger by three years) because Cameron had killed their father and stolen the money his father hid under his matress. It didn't help their relationship when Cameron slept with Josie in 1998, but they reconciled in 1999.
Gary also has a sister and another younger brother.
Gary Sinclair Jr. (RIP) was Gary's nephew, Cameron and Josie's son from a one-time affair. Upon learning of the pregnancy, Josie passed the child off as Gary's. The baby was born prematurely on March 4, 1999 in the hospital. Wanting to save his presumed son's life, Gary planned to take part in a blood transfusion. Gary was devastated when Josie blurted out that he was sterile and Cameron was the father. Gary Sinclair Jr. didn't survive surgery, dying just a few weeks after being born. A small funeral was held for him, where Gary said a heartfelt goodbye to his nephew.
Gary became involved with Jackie Warren, a fellow police officer, in 1992. He was then assigned by his superiors to work undercover to root out crooked cops, of whom Blair was one. She was sent to jail and swore revenge. Upon her release she made her way to Bay City and insinuated herself into Josie's life under the pseudonym of Blair Baker. By the time she came face-to-face with Gary, she had mellowed and was willing to leave Gary alone. Despite this, Gary was paranoid that Blair would still come after him. Feeling herself backed into a corner, Blair went on the offensive. She ended up shooting Josie before being gunned down herself by the Bay City stalker.
Cecile came on to Gary one time when he visited Wallingford's in 1996. She made the mistake of offering to buy him a drink.
Gary was an alcoholic. He fell off the wagon for a brief period in the summer of 1995. In 1996, Blair Baker forced Gary to drink some liquor to get him drunk. Since then he remained sober with the assistance of his sponsor, Felicia Gallant, and his wife, Josie Watts.
CURRENT AND FORMER OCCUPATIONS
Gary was an instructor at the Bay City Police Academy before being promoted to lieutenant the summer of 1995.
He was suspended for being drunk and disorderly in 1996. Although he had been set up by Blair Baker, Internal Affairs refused to reinstate him without a full investigation. Gary refused to jump through hoops for them and quit the force. He continued to work secretly on the Bay City stalker case. His role in its successful completion led to his full reinstatement with much ceremony.
In early 1997, Gary began breaking the rules in order to catch the bad guys. IA caught up to him and demoted him. Rather than face that humiliation, he resigned and opened up a detective agency in May 1997. At that time he had a total of 57 collars and 52 convictions.
Gary held a job as chief bus boy and bottle washer at Carlino's Restaurant in the summer of 1996.