As terrific as Roy Halladay is, does he merit something approaching 20 million dollars annually, and the loss of several top prospects, e.g. Buchholz and Kelly? If I'm ownership, I can't go in that direction.
Yes the Sox need a right-handed bat, and there are a few directions there, including Adrian Beltre. Whether Mike Lowell can handle the full load next year can't be known to Sox fans, and Beltre has considerable pop in his bat.
The Sox are rumored to want to lock up V-Mart heading into his contract year. Jason Bay? The news all seems negative, from money to location, and J-Bay looks like he's earned a Godfather contract, although the 5-6 week stretch of distress against breaking stuff away mid-season gives me concerns.
Among the possible pitchers, the best 'bargain' could be Justin Duchscherer, a former Sox farmhand, who has had health issues. Sure, you have the tantalizing Rich Harden, he of the DL, and Ben Sheets, ditto.
Reportedly, Brad Penny has found a new pitching home in St. Louis. Penny just never seemed comfortable in the AL, with great stuff and not so great results with selective hitters in the AL.