A Halladay in Boston?

The NY Daily News is reporting that the Red Sox are making a strong push to acquire Toronto’s Roy Halladay.  This would be a great acquisition for Boston, but is it the best way to upgrade the pitching staff?

For starters, it might take a package of Clay Buchholz, Casey Kelly and another 1-2 prospects (and maybe Daniel Bard) to make the move (I’m not here to suggest the above is the necessary package of players, just trying to introduce a concept).  Then, once here, Halladay would require an extension, 5 years at between $80mm or $90mm ($16m – $18mm per year) sounds about right.

Or perhaps the Red Sox just go out and sign John Lackey.  Lackey isn’t as good as Halladay, but he also wouldn’t cost as much and still provide a solid #2 pitcher.  Consider, signing Halladay would cost lots of money and lots of talent.  Signing Lackey would cost less money and only a 1st round pick in the 2010 draft.

You tell me, assuming both moves prove possible, which is the best approach?

Halladay is awfully tempting but would probably negate any possible offensive upgrade using prospects (names like Adrian Gonzalez and Miguel Cabrera have been mentioned).  In addition, whether or not the Red Sox re-sign Jason Bay will play into this as well.

To me, if the Red Sox can re-sign Bay, I’d make the Halladay move.  Jon Lester, Roy Halladay, Josh Beckett would be a compelling 1-2-3, wouldn’t it?  If they cannot sign Bay or Matt Holliday, I think the focus needs to be a trade to upgrade the offense.

In an ideal world, I’d see the Red Sox re-sign Bay, trade for an offensive upgrade at shortstop or the corning infield and get Halladay.  That would make this a great off-season for Boston, but I’m not sure the minor league system has enough ammunition to get all of that done.

As we approach and enter the Winter Meetings (Dec 7-10), we should start getting some clarity on what the Red Sox will look like in 2010.