Right now, I do not want to make a trade for a pitcher. There is a plenty good option out there who is younger than Halladay, has more playoff experience and is a free agent in Lackey. Now, Halladay is undoubtedly better, but signing Halladay will require probably a 6 yr deal. Signing Lackey may be a 5 yr deal. The question you need to ask yourself is which one is better, column A or column B assuming Halladay will get a 6 yr $110 mil deal and Lackey would get a 5yr $90mil deal
Column A:
John Lackey for ages 31-35, $20 million less in commitments, and 2 of Montero, Hughes, Jackson, and Chamberlain
Column B:
Roy Halladay for ages 33-38, and you get to keep the 2010 first round pick
When you look at the stats, I dont think the extra acquisition cost is worth it. Halladay's career WHIP is 1.20. Lackey's is 1.30, Halladay's career ERA is 0.40 better than Lackey's. Halladay has thrown 4 200IP seasons over the last 4 seasons, while Lackey has essentially had 5 over the last 7. Both are durable. Both keep walks to a minimum. Halladay is better, but when you consider the fact that whomever we get will occupy either the #2 (Halladay) or #3 (Lackey) role on this team, then I dont think you need to go over the deep end. C.C. changes this whole dynamic. Also, one must consider that Halladay is 2 yrs older and in all likelihood would need to have an extra yr on his deal. So the ages of acquisition matter, a lot.
Also, you need to factor in the fact that dealing for Halladay gives you one year of control, so it isnt like last yr when you would have had two seasons of control. So, right now, I would not trade Hughes or Montero for him at all (since I think Hughes is going to have a very strong career as a starter and Montero is a special, special bat). Now, if Pettitte hangs em up, Boston signs Lackey, and no other tradeable options hit the market, then I would be a bit more inclined to deal for him. But my maximum offer would be either Joba + lower level prospects or AJax + lower level prospects. I would be very reticent to deal both Joba and AJax and I would pull Hughes and Montero off the table altogether. I know that wont get the deal done, but I am very wary of dealing high end talent for a mid 30s pitcher.