Philip

Well well well, Phil Cassidy, the one-armed bandit. Here's his timeline/story: (contains spoilers, some events made up by me)

1950: Phil is born in Vice City.

1953: Phil kills a teacher in Nursery School. It is the first person he will kill.

Veitnam War: Phil fights for the A.R.M.Y. in 'Nam. Source: GTA: VC Dialogue.

1984: Phil does business with Victor Vance in Vice City. Source: GTA: VCS Trailer.

1986: Phil does business with Tommy Vercetti in Vice City. He owns a shop in Vice City. At one point, he is playing around with Boomshine and his arm is blown off. Source: GTA: VC.

1986/1987: Phil closes his shop in Vice City and moves to Liberty City.

1998: Phil opens up shop (a Heavy Weapons Shop, in fact) in Liberty City. Source: GTA: LCS.

2001: Phil opens up another shop (but keeps the other one, as well) in Liberty City. Then he does business with Claude Speed. Source: GTA III.