For the first question... a little clue : There is only one active player who shares the thing in common with the other pitchers named. He was a Detroit Tiger when he acquired the common trait of those other players.

Hint for the second question: Of the members participating in the Challenge Game, one might reasonably conclude that Geoff would have the best chance of answering the question as he very well may share the common characteristic. In the world of entertainment, Bruce Springsteen and Eddie Murphy are also in this group.