Derek Jeter: Why He'll Go Down As Most Overpaid Player in MLB History

Derek Jeter is, for the first time in his career, a free agent.

After spending his entire career with the New York Yankees, it seems absurd that he would end up anywhere else but in New York.

But after a bad season in New York, does he deserve big money to finish his career?

When all is said and done, people will be scratching their heads at Jeter's contract, no matter who he signs with.

10. He Is a Yankee

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NEW YORK - OCTOBER 19: Derek Jeter #2 of the New York Yankees runs back to the dugout against the Texas Rangers in Game Four of the ALCS during the 2010 MLB Playoffs at Yankee Stadium on October 19, 2010 in the Bronx borough of New York City. The Rangers

Jeter knows that he is going to end his career with the only team that really would overpay him. After spending all of his 15 seasons in New York, would the Yankees really let him sign elsewhere?

The answer is absolutely not. Jeter just has to be patient if he really wants a four- to six-year deal worth $20-25 million a year, because the Yankees will give it to him.

Would anyone else offer him that?

Heck no.

9. He Can Go to the Mets to Drive Up His Value

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NEW YORK - OCTOBER 19: Derek Jeter #2 of the New York Yankees smiles during batting practice against the Texas Rangers in Game Four of the ALCS during the 2010 MLB Playoffs at Yankee Stadium on October 19, 2010 in the Bronx borough of New York City. (Ph

If Jeter isn't getting enough love from the Yankees, he could always head to Queens to discuss a contract.

The Mets would be desperate to make a mark for themselves in the New York market, and there is no better way to do that than to sign their crosstown rival's franchise player.

8. He Is the Yankees' Captain

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NEW YORK - JULY 16: Captain Derek Jeter #2 of the New York Yankees speaks during the ceremony for owner George Steinbrenner and Yankee Stadium public address announcer Bob Sheppard before the game against theTampa Bay Rays on July 16, 2010 in the Bronx b

Derek Jeter is just the 14th captain in Yankees franchise history. If the Yankees don't do everything possible to re-sign him, they could lose the clubhouse.

Granted, Jeter isn't going to make or break the season for the Yankees, but his presence in the clubhouse will drive up his price.

7. 3,000 Hits

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NEW YORK - OCTOBER 19: Derek Jeter #2 of the New York Yankees hits a triple in the third inning against Tommy Hunter #35 of the Texas Rangers in Game Four of the ALCS during the 2010 MLB Playoffs at Yankee Stadium on October 19, 2010 in the Bronx borough

This season, Jeter could become the first player in the history of baseball to get his 3,000th hit as a member of the Yankees. The lead-up to that, as well as the merchandising that the Yankees are sure to do for that historic event, will drive up Jeter's value.

Just imagine the money the Yanks will make off the 3,000th-hit shirts and hats. Throw in the fact that every sports media outlet will be talking about Jeter during the lead-up to the hit and after the hit that the Yankees would get nothing but bad publicity if they fail to re-sign him.

6. Jeter Can Afford to Wait

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NEW YORK - OCTOBER 19: Former Yankees' pitcher David Wells talks with Derek Jeter #2 of the New York Yankees during batting practice against the Texas Rangers in Game Four of the ALCS during the 2010 MLB Playoffs at Yankee Stadium on October 19, 2010 in

Derek Jeter doesn't need to be in a hurry to sign a contract with the Yankees that he isn't completely sure about.

It will do nothing but look bad on the Yankees if they wait for Jeter to get other offers from teams.

Jeter's value to the Yankees has nothing to do with his free-agent market value.

5. Age

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NEW YORK - OCTOBER 19: Derek Jeter #2 of the New York Yankees smiles during batting practice against the Texas Rangers in Game Four of the ALCS during the 2010 MLB Playoffs at Yankee Stadium on October 19, 2010 in the Bronx borough of New York City. (Ph

Derek Jeter is currently 36 years old. If he were to sign a four-year deal, he would be 41 at the end of the contract.

For someone 41 years old to be making $20-25 million a year is silly.

If anyone deserves that money on the Yankees, it is someone like Robinson Cano, who has lots of years in front of him and an endless amount of talent.

4. Position?

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NEW YORK - OCTOBER 20: Derek Jeter #2 of the New York Yankees turns a successful double play over a sliding Michael Young #10 of the Texas Rangers on a ball hit by Josh Hamilton #32 in the top of the fifth inning of Game Five of the ALCS during the 2010

Apparently the only people who don't realize that Jeter isn't an elite shortstop anymore are Jeter, the Yankees and Gold Glove voters.

Jeter winning the Gold Glove this year was the biggest travesty since Shawshank lost the Best Picture Oscar.

But seriously, where is Jeter going to play going forward? He can't play first because of Mark Teixeira. I guess he could squeeze into the outfield, but with some good young talent there, shortstop is the only real place where the Yankees have room for Jeter.

Unfortunately, that is also arguably the toughest position on the field.

3. Compensation for Past Performance

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NEW YORK - NOVEMBER 06: Derek Jeter #2 of the New York Yankees and actress Minka Kelly (L) ride a float during the New York Yankees World Series Victory Parade on November 6, 2009 in New York, New York. (Photo by Michael Loccisano/Getty Images)

If the Yankees are going to pay Jeter for past performance, then he deserves to make a lot of money. I am not willing to say he deserves $20-25 million a year, but he deserves a lot.

The problem with that is Jeter could be one of the highest-paid players in baseball, yet have some of the worst stats, or, even worse, no stats.

2. Decline

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NEW YORK - OCTOBER 18: Derek Jeter #2 of the New York Yankees reacts after he struck out in the bottom of the sixht inning against the Texas Rangers in Game Three of the ALCS during the 2010 MLB Playoffs at Yankee Stadium on October 18, 2010 in New York,

Jeter had a huge decline in his stats this season.

179 hits - T-second-lowest of career

10 HR - T-lowest of career

67 RBI - Third-lowest of career

106 SO - Fifth-highest of career

.270 BA - Lowest of career

.340 OBP - Lowest of career

.370 SLG - Lowest of career

Needless to say, Jeter isn't getting any younger, and with the numbers decreasing, is it worth paying him what he wants to stay?

1. A-Rod's Contract

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ARLINGTON, TX - OCTOBER 15: (L-R) Derek Jeter #2 and Alex Rodriguez #13 of the New York Yankees celebrate after the Yankees won 6-5 against the Texas Rangers in Game One of the ALCS during the 2010 MLB Playoffs at Rangers Ballpark in Arlington on October

Alex Rodriguez and Derek Jeter used to be close friends, however in recent years their relationship has cooled.

That could be in large part to the record-breaking contract that A-Rod signed a few years ago. A-Rod is making about $27.5 million a year until 2018.

Jeter obviously feels that if the Yankees can afford that for A-Rod, they can afford to give Jeter what he wants.

Can you blame him?