- Brad Penny has proven himself to be a wildly successful gamble whose value increases with every start. Do the Sox trade him - and if so, to whom, and for what - or do they choose to ride his success to the post-season and possibly beyond?
- John Smoltz, Clay Buchholz, and Dice-K Matsuzaka are competing for a rotation spot. For now, the Sox are opting for a six man unit, but for the sake of their pitchers' rhythms, they'll have to make a decision one way or another before too much times goes by. Who should get the job?
What makes Boston's position even more enviable is that the Sox don't have to make a decision quite yet: they have the time to see Smoltz become a known quantity and if he doesn't work out, keep Penny for the rest of the season or trade him and fall back on Buchholz. If Smoltz proves himself up to his usual standards, they can trade Penny and pitch Buchholz, or keep Buchholz in the wings and hold on to Penny.
My thoughts: wait and see on Smoltz and trade Penny no matter what - but only after Smoltz has had time to establish himself. Unless Penny somehow goes off the deep end between now and the trading deadline, his value will remain high among contending teams desperate for good pitching and the Sox might be able to get a solid catching prospect in return. In addition, a trade will give Boston some value on an expiring contract for a pitcher who will command a lot more money on the market this winter. Waiting until Smoltz proves himself just increases the options in case of a worst case scenario. Either way, they should still DL Dice-K until he's really healthy before putting him back in the mix.