Sort of in the vein of ‘experience a dude’.
Say you get a choice of one drifter to experience and have him join a faction. Who is it and which faction would you have 'em hook up with?
Personally after the dust up between Sloane and Law Dogs, I see Olivia Jenks helping out her husband more.
How bout you guys?
Well, Steve Wiles is pushin’ up daisies 
So how about Jackie Isham helping out the poor, beleagured Clowns constantly coming under attack 
Mario Crane joins the Law Dogs, has a slight Dominion problem and becomes a one-man good cop/bad cop duo.
The Sloane Gang and the Law Dogs are each down a lawyer. They next clash in the offices of B&B when they both send a posse to recruit Androcles Brocklehurst to their side.
On a more serious note, Max Baine could assist the 108 Righteous Bandits in taking down the MCC.