The two biggest free agents to walk off the 2009 Champion team are Hideki Matsui and Johnny Damon. One DHed while the other played an atrocious left field, but they both pulled their own weight at the plate. While earning a total of $26mm, the center-fielder-turned-left-fielder and the left-fielder-turned-DH combined for 52 homers, 172 RBI’s, and 1,006 at-bats. Their departure leaves two big holes in the lineup. As of right now, it seems like top prospect Austin Jackson will man centerfield while Melly Cabrera moves to left. This obviously still leaves a spot in the order to be filled, and in a big way as Jackson is unlikely to fill the shoes offensively of neither Matsui nor Damon. The question now, for the Yankees, is: who should fill that hole?

The two biggest names on the Free Agent market both happen to play left field. They are both right-handed, which would work against them in the lefty-loving Yankee Stadium. With two strong left-handed bats meeting free agency, the Yanks would prefer to bring in a powerful lefty, but the best players bat from the side closest to third. There is speculation about Matsui or Damon returning to the Bronx, but their age (35 and 36 respectively) and inability to do much while wearing a leather glove cause hesitation from the front office in regards to resigning. If either were to sign, it would likely be Damon, who would DH regularly, but play the field when another veteran needed a semi-off-day. Even if Damon were to sign, the Yanks would likely look for another bat, someone who could play left and/or center. While the Yanks plan to promote Jackson, they will be hesitant to end their every day lineup with him and Cabrera. The acquisition of a competent outfielder would allow the team to trade either Cabrera or Gardner, with the other becoming a 4th outfielder, and insurance in case Jackson’s first season in the Bronx ends more like Rondell White’s than Derek Jeter’s. So, I might as well stoke the fires of the hot stove.

Matt Holliday, Jason Bay, and Mike Cameron are the only three outfielders that I’ve heard much Yankee-based speculation about. Holliday is clearly the market’s best player. He is younger than Bay, is a better hitter than Bay, and is a better defender than Bay. To his credit, Bay has endured the Boston pressure cooker, while Holliday has played in Colorado, Oakland, and St. Louis, all cities where the media coverage, in comparison to Boston and New York, is like a four-year-old kid with a Magic Microphone asking, “How does it feel to be famous?” Still, Holliday is a better player than Bay, and he’ll be paid accordingly. The Yanks have already committed long term to Alex Rodriguez, Mark Teixeira, AJ Burnett, and CC Sabathia, not to mention the new contract Jeter will inevitably sign by this time next year. Thus, the team should be hesitant to add any more long-term, big-money deals this winter. I’m not saying that a Holliday or Bay signing is impossible, but I will say that it is unlikely. Look for the Yanks to get involved though, if only to raise the price for whichever left fielder signs in Boston.

Cameron, also a righty, will be 37 in January. The Yanks, it seems, have always loved Cameron. He’s a friend of CC Sabathia’s and almost became a Yank in a trade for Melky Cabrera and Kei Igawa last winter, but that broke down when the Yanks tried to make Milwaulkee pay part of Igawa’s salary. Cameron’s .250/.342/.452 offensive effort was less impressive than Damon’s .282/.365/.489 and Matsui’s .274/.367/.509. Hell, it wasn’t really that much better than Melky Cabrera’s .274/.336/.416. He did play a strong center field though, with a UZR of 10 in center field. Cameron, at 37, is old (in baseball years, at least), which the Yanks don’t need to deal with. However, he is a possible option for the team on a one year deal. An outfield of Jackson, Cameron, and Swisher would be the best defensive 7-8-9 the Yanks have fielded in the past decade, if not longer.

The Yanks, though, may look to trade for a power-hitting lefty to make up for the loss of Damon and Matsui. Adam Dunn is an option, although he’d need to primarily DH, forcing Johnny Damon (if re-signed) back to left, and weakening the defense. I would love a Dunn trade, even if it means no return of Damon. With DunnĀ  primarily DHing, but capable of playing the outfield corners and first on occasion, the Yanks could sign Cameron (instead of Damon) to play left or center, depending on where Jackson seems best fit. The Rockies’ Seth Smith could be the odd man out in Denver with Brad Hawpe, Dexter Fowler, and Carlos Gonzalez set to start everyday, and Ryan Spilborghs being a more than capable 4th outfielder. Smith’s .293/.378/.510 performance in 335 at-bats was one of the most underrated performances of the year. Smith played a strong left field to complement his offensive performance, boasting a 6.8 UZR. Guess what; Smith’s a lefty. That means his 15 homers this year could jump to 25 or 30 as he racks up not only more at-bats, but more at-bats with a short right field porch to catch his fly balls.

Also in the Colorado organization, Matt Murton, who spent the year at triple-A Colorado Springs, could be an interesting trade candidate. His .324/.389/.489 line in the Springs might translate to big league success. The Nationals’ Josh Willingham smacked 24 homers this year while hitting .260/.367/.496 and playing subpar defense at the outfield corners. Those two right-handed hitters are obviously lesser options than Dunn and Smith, but they’d also be easier to trade for.

Detroit’s Curtis Granderson is available, but had an off year in ’09, and may cost too much in terms of prospects. Austin Jackson projects to be a Granderson-type player within two or three years, and Jackson would need to be involved in any deal for Granderson. Thus, a deal seems unlikely and unneccessary for the Detroit centerfielder.

The Yanks have a lot of options for patching the holes left by Damon and Matsui, but some are riskier than others. Some are more expensive than others. Some are foolish than others. My personal favorite plan: Deal for either Adam Dunn or Seth Smith, then sign Mike Cameron to a one-year deal while letting Damon and Matsui walk. This situation would also allow the Yanks to deal away either Melky Cabrera or Brett Gardner.