If she retains the option to keep less than 5, I would probably keep less. For a 10 team league, I would assume that this is a team near the bottom of the league.
If I HAD to keep 5 I would keep:
Wieters, The Baconator (Miggy), Wright, Hamels, Jay Bruce
However, I would drop Jay Bruce if I could keep less than 5 because I don't see him as much more than a platoon player for the next year or so. Can't argue with his power though...
With only keeping 5 players, I don't think you can keep a closer. It would be hard for me to keep a pitcher as well, but I could argue keeping Hamels. I wouldn't risk keeping Peavy with his elbow issues right now. That said, I'd go with