Sailor is shown to be a confident yet caring character. His route is spent searching for a medkit to help his roulette partner Sandbag, who had been shocked on stage during the show's introduction. During the fountain interaction, Sailor is eager to jump in and swim around, but is disappointed when he's stopped and told he can't swim due to the shocker on his wrist. When running into Cupid in the shop, Sailor is quick to demand an attack on him, yelling at Eddie to "Get him!" and suggesting Eddie "Give him a good ol' flogging." If your group don't win enough chips in the gambling hall, when Vick's team confronts you Sailor will willingly offer his grandpa's compass in return for the medkit, further proving his dedication towards his friends. Near the end of the route, he also brings up he has a good judge of character, and it's how he brought this team together. Sailor is quite energetic, such as when he got disappointed when he couldn’t swim in the fountain due to the electric cuff on
He tends to speak like a pirate and is very silly
When buying info from Vick in the VIP room, he says that sailor was charged for "selling of illicit goods" which means that he was caught 'selling' weapons, medication, bootlegs, etc. When asked about his imprisonment, Sailor said that he was part of a 'crew' that 'gave weapons to the needy'. He also mentions that he folded to the police and got multiple other people caught who got a worse sentence. Sailor also mentions that by the time he got out of prison he would be 'like 30-40'.
