Reggie here goes into my design basket of "all or nothing" type of risk vs. reward.
Start him, Darragh, Anthea, Maria, and Rosaleen and you can go all in with a 5 stud, 4 draw. Just make sure to win the round, because you lose a stud and a draw for each dude you have to remove from your posse.
and, from the other side of the table, know that Reggie needs to work as part of a unit, so the individual parts can be out maneuvered.