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Posted: Tuesday November 10, 2009 11:43AM; Updated: Tuesday November 10, 2009 2:43PM
Cliff Corcoran
Cliff Corcoran>INSIDE BASEBALL

AL East: Red Sox, Rays take aim at the champs; Jays look to deal

Story Highlights

The Yankees and Red Sox will compete for Jason Bay and Matt Holliday

The Rays can't continue to punt a big offensive position (right field) any longer

Toronto will look for takers for Halladay, Hill and (in a perfect world) Wells

Matt Holliday
Matt Holliday will almost certainly get a hard look from the Yankees and Red Sox.
Jeff Gross/Getty Images
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Breaking down each team in the AL East heading into the offseason. Teams are listed in order of 2009 finish. Check out the other division previews here:

AL Central
AL West
NL East
NL Central
NL West

New York Yankees

PENDING FREE AGENTS: LF Johnny Damon, DH Hideki Matsui, SP Andy Pettitte, OF/1B Xavier Nady, 4C Eric Hinske, UT Jerry Hairston Jr., C Jose Molina.

PLAYERS WITH OPTIONS: None.

PROSPECTS ON THE VERGE: RP Mark Melancon, SP Ian Kennedy, CF Austin Jackson, SP Zach McAllister, C Jesus Montero.

BUILDING FOR: Their 28th world championship.

BIGGEST HOLES: Left field, designated hitter, the back of the rotation.

TARGETS: LFs Matt Holliday and Jason Bay, DHs Matsui and Damon; Pettitte.

BREAKDOWN: The Yankees' focus this offseason will be on how -- and whether or not -- to replace World Series heroes Damon and Matsui. They'll certainly be in the mix for Holliday and Bay, but after their spending spree last winter, could back off on long-term deals given that those two are just five and four years younger than the incumbents, respectively. Bobby Abreu's signing set the market for defensively-challenged, soon-to-be 36-year-olds who can still get it done at the plate at two years, $9 million per, though Damon and Matsui's increasing fragility may bring them in for less. Consensus is that the Yankees will only re-sign one of the two. As for the rotation, another one-year deal for Pettitte seems like a given, and one can't rule out a run at John Lackey, but the Yankees have shown commitment to their home-grown pitching prospects, which likely means Phil Hughes will return to starting chained by an innings limit while Joba Chamberlain will finally be fully unleashed. Expect the Yankees to also keep arbitration-eligible Chad Gaudin, who greatly improved his slider under pitching coach Dave Eiland, as insurance on those two, but to non-tender Chien-Ming Wang, who is coming off shoulder surgery that could have him rehabbing past Opening Day. As for the remaining free agents, Francisco Cervelli is ready to replace Molina. Hinske and Hairston would be worth keeping on the bench. Coming off Tommy John surgery, Nady is an afterthought and should be headed elsewhere.

Boston Red Sox

PENDING FREE AGENTS: LF Jason Bay, RP Billy Wagner, OF Rocco Baldelli, SS Nick Green, SP Paul Byrd, 1B Jeff Bailey.

PLAYERS WITH OPTIONS: C/1B Victor Martinez ($7.7/0.25M club -- exercised), SP Tim Wakefield ($4M club), RP Takashi Saito ($6M club), C Jason Varitek ($5M club/$3M player -- club declined), SS Alex Gonzalez ($6/0.5M club -- declined).

TRADE ACQUISITIONS: OF Jeremy Hermida (from Marlins for RPs Hunter Jones and Jose Alvarez).

PROSPECTS ON THE VERGE: OF Josh Reddick, SP Michael Bowden, SP Junichi Tazawa, RP Dustin Richardson.

BUILDING FOR: A return to first place -- ahead of the Yankees.

BIGGEST HOLES: Shortstop, left field.

TARGETS: Bay, LF Matt Holliday, SS Marco Scutaro, SS Orlando Cabrera, SS Miguel Tejada.

BREAKDOWN: The Red Sox made the no-brainer move to pick up Martinez's option on Monday, but they predictably declined Varitek's option. Boston needs to make it clear to Varitek that if he chooses to pick up his player option it will be to serve as Martinez's backup. The Sox have to be considered the favorites for Bay, but with the Yankees also looking for a corner outfielder, the price should be steep. Adding the young and talented Hermida for a pair of marginal minor league relievers gives Boston an in-house backup plan. Boston signed Wakefield to a two-year, $5 million deal as rotation insurance on Monday. Saito's a tougher call, given that his 2010 salary was inflated by the incentives he reached this year. Wagner will go elsewhere to close. The Sox will spend far more money to fill left field, but their toughest decision will be what to do about shortstop. Boston declined Gonzalez's option, but are the Sox willing to give Jed Lowrie another chance to be the de facto starter, coming off a season wrecked by wrist surgery? My guess is they'll bring in Scutaro and make Lowrie fight for another opportunity.

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