1) Determine the market for top free agent outfielders Carl Crawford and Jayson Werth.
Since midseason, these two names have been inexorably linked to the Red Sox. Crawford offers speed, defense and athleticism while Werth would provide the Sox, increasingly lefthanded, with some righthanded sock.
But the Sox will have no shortage of competition for both. After two seasons in which spending has been down across the board, the expectation is that teams are ready to splurge again.
"When it's all said and done,'' said one baseball executive, "I think people are going to be shocked at how much both (Werth and Crawford) get. It's going to be insane.''
Another executive estimated that while Crawford (right) should get a six-year deal, he'll likely end up with a seven-year pact. As for Werth, the same executive said a four-year deal would make the most sense, but thanks to the sheer number of teams interested, he'll likely land a five-year deal.
Crawford has been linked to the Los Angeles Angels of Anaheim, the Detroit Tigers and Texas Rangers. Werth is expected to receive interest from his current team, the Philadelphia Phillies as well as others.
If Crawford is going to get a seven-year, 120 million deal, as some expect, will the Red Sox consider that illogical? Ditto for Werth (left), for whom a Jason Bay deal (four-years, 66 million) once seemed likely, but now might be able to command a five-year, 80 million or more.
It's worth noting that since becoming general manager, Epstein has only given one deal longer than four years to a position player -- J.D. Drew's, five-year, 70 million contract after the 2006 season.
(It's also worth noting that that contract came after the last time the Sox failed to make the playoffs -- as they did this season).
The Sox have plenty of money to spend. With about 120 million in contractual obligations, they're some 45 million shy of last year's payroll figure. But it wouldn't be a huge surprise if the Sox sat on most of that money and instead budgeted it for in-season acquisitions (see 2009 -- Victor Martinez, Billy Wagner, Alex Gonzalez) or held onto the money with an eye toward next winter when a number of franchise sluggers (Adrian Gonzalez, Prince Fielder, Albert Pujols) hit the free-agent market.
Next: See what sort of interest exists for Daisuke Matsuzaka