He did co-found the Jets, so I imagine he's a little rough around the edges. It's just by the time the show starts he's sort of outgrown it all, or so he thinks.
At least, that's the impression I've always gotten.
And for the love of heaven, please stop suggesting belty altos for Maria. Karen Olivo in looks would be great, but you need serious soprano chops for Maria and I don't think that she has those.
Nitpick: Bailey's 20 or 21, not 19.
Jimmy, what are you doing here in the middle of the night? It's almost 9 PM!