First off, we are talking about the best pitcher in baseball. Period. There is no debate or discussion about this. In each of the last three years, Halladay has:
- Thrown 200+ innings
- Started 31+ games
- Won 16+ games
- Thrown 4+ complete games (nine in 2008)
He is also a five-time All-Star, winner of the 2003 Cy Young Award and has finished in the Top Five for Cy Young voting the last three years. He will likely do so again this year (currently 10-2, 2.79 ERA). Lifetime, Halladay is 141-68 with a 3.47 ERA
The closest comparable to this kind of deal is when Johan Santana was dealt from the Twins to the Mets in 2008. The cost to New York was their two top prospects (Delois Guerra, Kevin Mulvey) and two major leaguers (Carlos Gomex, Philip Humber). So Toronto will be looking for that kind of quality in a trade for Halladay.
So we've established why the Jays think he is so valuable and the kind of deal they'll want. But there are some negatives.
First, Halladay is well-paid. He gets $14.25M in 2009 and $15.75M in 2010. If a team wants to sign him to an extension, expect to pay that or more in the years ahead. He's also 32 years old. This is the last of the "prime" years (think 26-32). And while turning 32 isn't an automatic ticket to Slumpsville, teams have to be a little more cautious. Injuries take longer to come back from and can occur more easily. Combine these two things and some teams rumored to be interested in Halladay (Philly, St. Louis, Milwaukee) may have to think twice. Also consider how a pitcher paid at this level can upset the salary structure for a team. For example, Beckett's contract has a team option for 2010 at $12M. Will that satisfy Beckett if Halladay comes in getting paid nearly $16M? What would Beckett ask for in 2010? And consider that both Halladay's and Beckett's contracts expire in 2010. How much would it cost to resign these two?
Also consider that Halladay recently came back from a groin injury and, as Aviv mentioned, hasn't looked good. He lost to Tampa on June 29 and then got shelled by the Yanks on July 4 (7.0 innings, nine hits, five runs, three walks). Until Halladay produces a good post-injury outing, teams are going to be very cautious with trading for Halladay.
So the positives and negatives are laid out. Now the question; should Boston trade for Roy Halliday?
If the Jays were inclined to trade within the AL East, Boston is one of the teams that can match their asking price. The Sox could offer Buchholz, Michael Bowden and Lars Anderson (three of their top four prospects) and likely land Halladay. And if Halladay stayed healthy (which isn't a long shot at all), he could give Boston five more solid years of pitching. Combined with their current staff, Boston would have the strongest rotation in the game.
There is also this; the Boston farm is deep enough to take this kind of hit. Even with Buchholz and Bowden leaving, you'd have Tazawa and Felix Doubront in the wings. With Lars leaving you'd have young first baseman Anothony Rizzo moving up the ladder quickly and the power bat of Josh Reddick if you needed a DH. Unlike the Mets, trading for Halladay wouldn't leave the Boston system barren.
But in the end...I think the best-case scenario is Philly breaking the bank and Halladay going to the NL. There are just enough question marks about Halladay's long-term performance to make me hesitate on trading for him. If it was for just two prospects, I think the risk would be worth it. But to give all three...you want a guaranteed thing and right now Halladay isn't playing like a guaranteed thing. Moving him out of the AL altogether is the next best scenario.
The Yankees could get him but would give up a lot to do so. And as Aviv said, that's the kind of old Yankee move Cashman is trying to avoid. That said, I would bet Hank and Hal want to kick the tires on this one.
So as tempting as it is...I don't think Boston should pull the trigger on this one. But to justify that move we need to see Buchholz and Bowden in the majors next year. To keep them in the minors another year as "potential starters" would be a waste of their talent and utterly pointless. If you aren't going to have them in Boston, at least make it because you have Halladay in a Boston uniform.