CC Sabathia is heading into a very interesting period in his life. A September pennant race will give way to an October quest for his second World Series ring as a member of the New York Yankees. Win or lose, what comes next will be intriguing as well. 

Sabathia has an option with in the seven-year, $161 million contract he signed following the 2008 season to opt-out following this season. That basically means the existing contract is over and he’s a free agent again.

With Sabathia in the midst of one of his best seasons and no reason to expect him to quit playing baseball at the end of the seven-year deal he’s currently in the midst of, it seems more than likely that he will take full advantage of this opportunity for both a raise and an assurance of guaranteed money beyond his mid 30s.

Sabathia already is the owner of the largest contract for any pitcher in MLB history. Cliff Lee might be a better pitcher, but no one is paid more than Sabathia.

The real question is, would he leave the Yankees and if he would, where would he go? Impending free agents such as Albert Pujols and Prince Fielder are restricted to what teams they can go to by their position. There’s no such thing as having “too many ace left-handed starters” though. Sabathia can probably count on being contacted by almost every team that thinks they could compete financially for his services, and that list is longer than many Yankee fans might think. 

It all starts in Boston, of course. The Red Sox have experienced some real health issues with their starters this season. On top of that, it seems very unlikely that John Lackey will ever come close to fulfilling the lofty expectations set for him when he signed as a free agent in Boston. In spite of a number of big financial commitments, the Red Sox would be a major suitor for Sabathia. 

Who else would bid on Sabathia? Philadelphia. Yes, they already have Roy Halladay, Cliff Lee and Cole Hamels. Roy Oswalt may be done after this year, though. The Phils have already shown that you really can’t ever have too much pitching. If Philadelphia brass feels like the younger up-and-coming offensive players can shoulder the load of producing runs, then they may not be so gun shy in spending big to acquire yet another guy to keep runs off the board.

The Chicago Cubs, Washington Nationals, Texas Rangers, Los Angeles Dodgers, New York Mets and San Francisco Giants could all get involved as well.

For the Cubs, Sabathia would be the ace that Carlos Zambrano never really became. Sabathia is everything Zambrano isn’t. He’s a likable player with an easy going attitude that seems to please teammates, fans and his bosses. Contrast that with the abrasive and temperamental Zambrano, and he’d be the perfect way for a new Cubs owner to help fans and media forget about Zambrabo’s combative ways.

The Nationals have shown a willingness to over pay for a player they covet. Jason Werth’s deal last winter set that precedent. Would they covet Sabathia? Probably, although with Stephen Strasburg seemingly back and healthy the Nationals don’t really “need” an ace. Yet as a one -two top of the rotation Sabathia and Strasburg would be quite formidable.

The Rangers have a long and decorated history of not retaining top pitching. Should CJ Wilson depart as a free agent this offseason, then the Rangers would be in desperate need of a top starter.

Sabathia would fit the bill, but can the Rangers really expect him to want to pitch in a ballpark that favors hitters even more than Yankee Stadium? Would Sabathia want to subject himself to pitching in 100-degree-plus temperatures for the better parts of his future summers? Unlikely.

The Dodgers and Mets both have the big-market appeal, but currently lack the big money that usually accompanies it. It’s very unlikely that Sabathia would choose to remain in New York City but go to a team with a much greater chance of missing the playoffs. It’s also unlikely that the Dodgers will have the money to pay Sabathia.

The San Francisco Giants have a few things going for them. One is that Sabathia is from the Bay Area originally. Players returning to locations near where they grew up is not all that uncommon. The Giants also play in a division that seems to favor pitching.

The Giants also recently won a World Series and have a number of talented pitchers on their roster. The addition of Sabathia would place the Giants right back at the top of any discussion about serious World Series contenders.

In spite of a long list of potential suitors, it seems highly unlikely Sabathia will leave the Yankees. The Yankees provide Sabathia with just about everything he wants. He’s the arguably the most important player on the team. Regardless of whether or not the Yankees win a championship this season, Sabathia is an irreplaceable player on the roster.

There is no “ace” in the Yankees farm system and there aren’t any aces coming up as free agents anytime soon. Should Sabathia opt out of his current deal, the results are more than likely to be an extension of his existing deal and perhaps a small raise on an annual basis. The Yankees misread the market and missed out on Cliff Lee last offseason. They’ll make no such mistake this upcoming one. 

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