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Why Lackey Was a Better Fit Than Halladay

12.16.09 at 4:32 pm ET

At the 2009 trading deadline, the Red Sox made an aggressive play to acquire Blue Jays ace Roy Halladay. The team reportedly offered a 5-for-1 package that was centered by Clay Buchholz, three other pitchers and outfielder Josh Reddick. The Jays declined to make the move.

This offseason, the Sox once again kicked the tires on Halladay, but it remained clear that the cost to the Sox for the 2003 Cy Young winner — a combined hit of prospects and a long-term contract extension — would lead to an imbalance in the team’s pursuit of short- and long-term success. Halladay would have cost the Sox several key prospects, not to mention upwards of $75 million over the next four years.

Lackey, by way of contrast, cost the team plenty of money (five years, $82.5 million), but did not require the team to part with any of its key prospects. And while the Sox will have to give up a first-round draft pick for Lackey (one that would have gone to the Blue Jays for the Marco Scutaro signing, and that will instead now go to the Angels), the team should conclude this offseason with a net increase of two draft picks.

The Sox will lose both their first- and second-round picks for the signings of Lackey and Scutaro. But the team will get the No. 20 overall pick in the draft from Atlanta as a result of the departure of reliever Billy Wagner, and the Sox will get a draft pick from a team that signs Jason Bay (a first-rounder from some clubs, though if the Mets sign Bay, the Sox would get New York’s second-round pick, since their first-round selection is protected), as well as two draft picks in the sandwich round.

On balance, then, the Sox feel that the moves that they’ve made thus far to sign free agents Lackey, Scutaro and Mike Cameron have left the club in better long-term position than would have been the case had it pursued a player such as Halladay in the trade market. The Sox have retained all of their best prospects this offseason and they have added draft picks. It’s been expensive in terms of dollars, but the overall cost to the organization has been a reasonable one.

“We had interest in Halladay dating back to the trade deadline and early in the offseason,” said Sox GM Theo Epstein. “Well before [Halladay] was moved, it was clear he wasn’€™t going to be a factor for us based on the asking price, which is reasonable. I think [Blue Jays GM Alex Anthopolous] did a really good job. We weren’€™t prepared to pony up the prospects in addition to the salary that would have been required.

“We’€™re in a pretty good spot now. If you look at what we’€™ve done, I do think we’€™ve improved the 2010 red sox. I think we’€™ve improved our long-term outlook. We’€™ve added draft picks, we hope to add more draft picks ‘€“ I think we probably will ‘€“ and we haven’€™t touched our prospect inventory at all. All of those different factors contribute to a healthy organization, what your team looks like next year, what it looks like in the future, what your commitments look like, what your draft-pick bounty in next draft, and how many prospects you’€™re able to retain, at least ones you believe in. In all of those areas, we feel like this is a pretty good solution for us.”

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