Roy Halladay to the White Sox?

Peter Gammons was on ESPN 1000 with Waddle and Silvy today, and the possibility of Roy Halladay to the Sox was a major topic.

Blue Jay's GM J.P. Ricciardi recently said that they'll have to at least listen to offers for their ace starter, and the Sox seem to make a lot of sense as a landing spot. They've already tried to acquire an ace pitcher once this season, and they seem to have the requisite young talent to make an offer.

Gammons stated that he, "would be absolutely floored if Kenny (Williams) doesn't make a serious attempt to get J.P. (Ricciardi)'s attention."

Frankly, I'm rather torn on this issue.

On the one hand, Halladay would clearly be a massive upgrade in their starting rotation. He is one of the best pitchers in baseball, and has been phenomenal this season.

The Sox would have one of the strongest rotations in baseball if this deal were to happen. Their pitching is already second in the AL in ERA thanks to the performances of All-Star Mark Buehrle, youngsters John Danks and Gavin Floyd, and the rejuvenated Jose Contreras.

That's not a staff that you want to face in the playoffs. Yes, I said playoffs. In my opinion the Sox are already in a strong position to win the division even before factoring in the potential impact of a starter with Roy's ability on the race.

I worry about the level of talent it would cost for the Sox to acquire "Doc," though. Rumor has it that Toronto will be looking to acquire at least four solid pieces for their prized starter. I'm sure they're asking for Gordon Beckham (whom I highly doubt is available) and would not settle for anything less than Aaron Poreda, Tyler Flowers, Dan Hudson, and another player like Jordan Danks, Dexter Carter or Brandon Allen.

That's a steep price to pay, especially given Halladay's age and contract status. The ace starter turned 32 in May, and his contract expires after the 2010 season. You're only guaranteed to have him in your rotation for a year and a half, after that you will likely have to pay at least $16 million per season to a 33-year-old starter.

Pitching also hasn't been the main issue for the Sox this year, especially over the last month. Granted, it would be nice to replace Clayton Richard with Halladay in the rotation, but the Sox biggest issue has been their defense.

Their offense has also struggled for much of the year. Though they have hit better of late, their lineup still seems like it could use a boost more than the rotation, especially if Carlos Quentin doesn't return at full strength.

The future makeup of the team should also be considered. I have a hard time seeing the organization bring back Jim Thome and Jose Contreras next year, and the return of Jermaine Dye is also in doubt. That could be three key pieces of the team leaving the organization, and Halladay would likely put a serious dent in the money available to replace them.

Can the team really win with that makeup after this year? Frankly, I don't know.

The rotation would be a monster, but the lineup would lose a significant amount of production, and at least a few of the young players currently expected to replace those guys would be in Toronto in this scenario. The offense would be almost entirely dependent on the production of younger players like Quentin, Beckham, and Ramirez. It would be extremely important that the Sox bring in a major bat, which probably won't be easy to find.

Whether or not this deal makes sense ultimately comes down to the asking price. If the Sox can hang on to Beckham, as well as at least one young hitter that can contribute in the near future like Danks or Flowers, then it probably makes sense.

If Toronto asks for the moon, the Sox may be better off standing pat. Personally, I don't see any reason to rush things. Young players like John Danks, Floyd, Beckham and Quentin have already shown that they have plenty of ability, and they have a few more highly regarded prospects waiting in the wings.

The Sox appear to be in a transition period where they are starting to work some young talent into the lineup, but are still mostly relying on veteran players. Over the next couple of years, the goal appears to be to replace their older, more expensive players with younger, cheaper players to hopefully give them payroll flexibility while still being competitive.

Halladay would drastically change that approach. He would clearly shift the team into more of a win-now mode, which could put them in a tough situation in 2010 and beyond. This deal would cost them several of their best prospects, so they will be faced with the prospect of spending a significant amount of money to re-sign or replace many of their veteran players or risk falling out of contention.

I would certainly be happy with the prospect of Roy Halladay pitching for the White Sox. However, I hope that Kenny Williams doesn't become too infatuated with winning now at the cost of the future.