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The Yankees Could Be Buying This Halladay Season

Doug Rush@Doug_RushSenior Analyst INovember 29, 2009

TORONTO - APRIL 6: Roy Halladay #32 of the Toronto Blue Jays delivers the pitch during the Opening Day game against the Detroit Tigers at the Rogers Centre on April 6, 2009 in Toronto, Ontario. (Photo by: Dave Sandford/Getty Images)
Dave Sandford/Getty Images

With Thanksgiving over and the Christmas season in full swing, baseball's free agency period and winter off-season shopping and trading will likely now pick up full steam.

The biggest name on the trading market is Blue Jays ace pitcher Roy Halladay.

Halladay's agent recently named four teams Halladay prefers: the Red Sox, Phillies, Dodgers, and Yankees.

Brian Cashman has already made calls to Toronto to state his interest in Halladay, who is looking to leave the only place he has known as home in his major league career.

With the free agent market for pitchers very thin, the Yankees may be taking the trade route to add to their rotation, which needs a little more help.

As of right now, the Yankees have two starters guaranteed for 2010 in CC Sabathia and A.J. Burnett. After that is where the mysteries are.

Andy Pettitte is a free agent and will be brought back as long as he puts off retirement again, so Pettitte would be back in the rotation, but that's only if he does return.

The other starters for the Yankees include Joba Chamberlain, Phil Hughes and Chien-Ming Wang. Wang is still recovering from major surgery and possibly won't be brought back by the Yankees if his injury is still serious.

That leaves Chamberlain and Hughes; both started in the rotation and were eventually moved to the bullpen.

Hughes was moved during the summer and became a dominant setup man for Mariano Rivera, while Chamberlain was moved during the playoffs as the seventh inning reliever for the Yankees.

With the Yankees having interest in Halladay for 2010, they both would likely be the focus points of a trade. The only question is, which one would the Yankees be willing to give up if they wanted to make a move?

Hughes regained his velocity, but struggled with confidence in the postseason and saw his playing time diminish in the World Series, while Chamberlain's confidence improved when he was used more in the Fall Classic.

So if the Blue Jays were to ask for one of them, Brian Cashman would have a tough decision to make.

There are other factors into making this possible trade for Halladay.

His age is a big factor. Halladay will be 33 in May, but he has been very durable for Toronto.

Halladay was 17-10 with a 2.79 in 239 innings in 2009, which is a ton of work for a starter. Some might feel Halladay could start to go on the decline, but he isn't just the average power pitcher.

Halladay uses a lot of movement with a curveball, slider, changeup and cutter that he uses to complement his fastball.

Plus, as he has gotten older, Halladay has become more of a pitcher instead of a hurler and uses his head to think about how to get hitters out.

The other factor is money.

Halladay is in the final year of his contract with Toronto and possibly would want a contract extension, a thing that has teams possibly balking at trading for Halladay because they might not be able to afford him.

Halladay could command anywhere from $16 million-$20 million per season, which is why the big market teams are the biggest players for Halladay.

The money factor also gives the Yankees an edge, because they really could make the deal if they absolutely wanted to.

The Yankees bring in more money than any other team in the league and know how to spend it well. Spending it on Halladay could prove to be a worthy investment.

There has been a lot of rumors that the Red Sox are aggressively pursuing Halladay as well, but they are also linked to trading for Felix Hernandez, Adrian Gonzalez, and Miguel Cabrera.

Boston clearly would not have enough players and prospects to trade for all the players they are interested in, so they would have to make a decision on who they would want to pursue.

The Yankees on the other hand, aren't looking at the trades as a necessity like Boston is, because they are the World Champions who will bring back a lot of the championship roster that will compete again in 2010.

The Yankees can almost wait to see what pans out before they make their move, just like they did in the pursuit of Mark Teixeira last winter when Boston screwed up those negotiations and Teixeira landed right in the Yankees' lap.

So now the questions, rumors, stories and speculation will all begin. Will the Yankees pull the trigger to get the best pitcher on the trade market?

Some feel they can, especially if they can stop Boston from getting him. Others feel like the Yankees might not feel as forced to get Halladay because of the issues.

The Yankees need to look into bulking up their pitching staff. In the 2009 postseason, they only went with three starters because they only trusted Sabathia, Burnett and Pettitte, but you can't do that in the regular season, so addressing the rotation will once again be a thing Cashman does for 2010.

If Halladay is available, the Yankees need to look into him and possibly move soon if other teams are going to get into the mix. If not, the Yankees will look elsewhere.

So get ready for the Halladay rumors to start heating up, because they will be all over the place very soon.

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