How Do the New York Yankees Approach Free Agency 2010?

Doug Rush@Doug_RushSenior Analyst INovember 19, 2009

NEW YORK - NOVEMBER 06:  Captain Derek Jeter #2 of the New York Yankees celebrates with the championship trophy during the New York Yankees World Series Victory Celebration at City Hall on November 6, 2009 in New York, New York.  (Photo by Jim McIsaac/Getty Images)
Jim McIsaac/Getty Images

At midnight, it begins.

Free agency basically ends everything from the 2009 season and begins the 2010 season.

For the 2009 World Series champion New York Yankees, it too begins their journey of defending their new championship that they worked hard to win.

Most people are probably wondering, where do the Yankees start in the offseason?

They have their own free agents to decide whether or not to bring back.

Most feel confident that Andy Pettitte will be brought back as long as he doesn't want to retire. In last year's offseason, Pettitte didn't sign with the Yankees until January 26, but that was only because the Yankees didn't see him as a priority in that offseason. They will now after he won four postseason games, including World Series Game Six, clinching the win.

Also, many feel that Pettitte is due for a pay raise from the $5.5 million he got in 2009, and because of what he did for the Yankees in 2009, a raise is absolutely necessary.

The other two free agents the Yankees have to make a decision on are Johnny Damon and Hideki Matsui.

Many feel that the Yankees want to bring Damon back after a strong 2009 season, but it all determines on what Damon and agent Scott Boras are looking for in a contract from the Yankees.

Some have said the Yankees are willing to go one year with an option or even two years. Anything else might be pushing it for Damon, but we all know how much of a greedy agent Boras can be. In the end, people still think Damon will be back in pinstripes for 2010.

As far as Matsui goes, nobody knows. He doesn't want to return to Japan, but nobody is sure if the Yankees want him back because of his inability to play the outfield due to his knees. If Damon needs to be moved to the designated hitter role where Matsui spent 2008-2009, Matsui doesn't figure into the plans.

However, nobody expected Matsui to go on the tear he did in the 2009 World Series, batting .615 with three gigantic home runs. He won the World Series MVP Award, so maybe the Yankees rethink their strategy on Matsui in 2010.

If the Yankees decide not to pursue Damon or Matsui for whatever reason, there are other options out there for left field and designated hitter.

At left field, the two biggest names out there are Jason Bay and Matt Holliday.

Both are looking for big paydays and are probably the two best position players on the open market for 2010.

Bay was traded from the Pirates to the Red Sox in 2008 and did a great job taking over for Manny Ramirez, but he rejected Boston's initial four year, $60 million dollar deal.

Bay played very well in one of the toughest divisions in all of baseball, but is also looking for a big time contract. No word has been given if the Yankees will be interested, but anything is possible with former Red Sox players. Just look at Damon before the 2006 season.

Holliday is another Boras client and supposedly is looking for at least $100-plus million. The Cardinals would love to re-sign him, but they have said they will only stay in it for a certain period. Again, nobody knows if the Yankees are interested, but he's another big name, and every big name is tied into the Yankees.

As far as the DH spot goes, just in case Matsui doesn't come back and if the other players aren't moved there, one player that has been rumored to be interested in coming to the Yankees is Jim Thome.

Thome, a former first basemen/designated hitter with the Indians, Phillies, White Sox and Dodgers. He is a first-ballot hall of famer with 564 home runs and is still a dangerous hitter from the left side.

He's almost 40 now and towards the end of his career that began in 1991, but he's been one of the classiest and likeable players in all of baseball and with his home run ability and leadership, could end up fitting in nicely with the Yankees clubhouse that has become a family.

Thome does strike out a lot, especially against left handed pitching, but when he does connect, the ball travels a long way. Plus, Thome has never won a World Series in his 18 year career and is looking for that one ring. The Yankees could be an attractive place for Thome to end his career.

Aside from offense, pitching is still going to be a question with the Yankees going into the 2010 season.

In the 2009 playoffs, the Yankees only used three starters in CC Sabathia, A.J. Burnett and Pettitte, so their rotation beyond that is in question.

Especially with young hurlers Joba Chamberlain and Phil Hughes. Both started out in the rotation, but Hughes became the set-up man and Chamberlain ended up in the bullpen for the playoffs.

Many feel that Chamberlain should be back in the bullpen because he's more dominant in that role and if Pettitte returns in 2010, more than likely, Joba will go back to the bullpen.

As far as Hughes, many still feel that he can be an effective starter if he uses his other pitches well aside from a blazing fastball and deadly curveball. But again, he was significantly more dominant as a reliever than he was as a starter, so the Yankees have to figure out where Hughes belongs in 2010 and beyond.

Aside from Sabathia, Burnett and with the possibility of Pettite returning, the Yankees have to figure out the rest of the rotation if Hughes and Chamberlain are not a part of it.

They could go after free agents like John Lackey, who is the top starting pitcher on the market and might not be back with the Angels. He could be a great front of the line starter for someone like the Yankees, who could add on to their rotation and get even stronger in 2010.

Aside from Lackey, Ben Sheets, Rich Harden, Randy Wolf and Jason Marquis are all available through free agency and could be other options if Lackey is signed by another team. Sheets missed the entire 2009 season with surgery to his arm, but had said he is all healed and ready to go for 2010. The only question with Sheets is, do teams give him a big contract, or do they steer away from his arm problems?

He might remain on the open market for a while if teams are not willing to take a risk. With the Yankees payroll, they can afford to take a risk on someone like Sheets, who could be a low-risk, high-reward type player.

The big name on the trading market for starting pitchers is Blue Jays Roy Halladay. Halladay is the big prized pitcher who will more than likely be traded before the 2010 season and the big market teams are all involved. Yankees general manager Brian Cashman has contacted Toronto about getting Halladay.

One of Halladay's best friends, Burnett, could even influence Halladay to come to New York and have him compete for a championship. Playing with close friends like that can only increase a team's probability in trading and signing someone.

With the new general manager in Toronto, one can only wonder what the Blue Jays are expecting to ask for in return for Halladay. Plus, if traded for, the Yankees could give Halladay an extension on his contract that others might not be able to afford.

The other need the Yankees can try to address in the offseason is the bullpen. During the playoffs, Hughes struggled, as did Alfredo Aceves, and Phil Coke. Brian Bruney hardly pitched, so it was mostly Joba Chamberlain, David Robertson and Damaso Marte pitching before Mariano Rivera.

Two names on the market have been linked to the Yankees interest; Atlanta Braves pitcher Mike Gonzalez and Rafael Soriano.

Both have closing capability and could also be setup men if needed. Gonzalez is a lefty who has had arm issues, but seems to be fully recovered. Soriano is a hard throwing, power right-hander who could draw interest from other teams looking for a closer.

These names are just some of the options the Yankees will weigh once Friday begins. It's been two weeks since the World Series concluded for the Yankees, and now, they are prepared to start over again for the next run.

The minutes are ticking away, so are those seconds.

The Blackberries and iPhone's will be working. Those frequent flier miles will be used. Free agency is upon is.

At midnight, it all begins. Enjoy!

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