Right now, it would seem the Indians are in between for 2010. One can make a persuasive argument that with Carmona coming back strong in the minors plus Huff and Rondon, the Indians rotation will be stronger in 2010. As for the bullpen, it can be argued that luck alone will provide improvement over 08 and 09. The offense has been impressive this season and there's few reasons to expect less for next year with LaPorta and Brantley close at hand and further improvement expected from Valbuena and Cabrera.
On the other hand, pessimists can say that the rotation is suspect and lacks depth, the bullpen will never improve without a change in front office philosophy that will require both asubstantial investment of money and several years of prospect development. Further, a pessimist could claim that regardless of the offensive talent, the Indians will not be contenders with the prospective roster they look to field in 2010.
With that in mind, I submit that the Indians should make a dramatic move in one direction or the other. To contend in 2010, the Indians will need more pitching and the easiest way to make a dramatic improvement to their pitching staff would be to add another front of the line starter. Roy Halladay fits that bill and is available. Dave Cameron offered his estimate of Halladay's value and my translation for the Indians is something like Hector Rondon (a given), Lonnie Chisenhall and Beau Mills (or Weglarz). Such a trade would strengthen the Indians rotation for 2010 without significantly weakening the ballclub for 2010. Ultimately, this scenario is most likely if Halladay isn't traded now but is traded after the season. In that case, the cost probably goes down marginally.
If this is too steep a price or Halladay doesn't want to waive his no-trade to come to Cleveland, the Indians should trade Cliff Lee and focus on contending in 2011 and 2012. As currently constructed, the Indians are a mediocre team that can be argued in or out of contention. Given the economic realities the team faces, it's unclear to me how the Indians will add significant talent from outside of the organization without making additional trades and I believe the bigger those trades, the better.