Derek Jeter

The New York Yankees spend huge amounts of money to be the best baseball team in MLB, translating the dollars into World Series Championships.

For the last 16 seasons, shortstop Derek Jeter has been the face of the franchise.

With the Jeter and the Yankees having trouble getting a contract worked out, will it really hurt the dynasty? 

While in his tenure with the Yankees, Jeter has helped lead the team to five World Series Titles.  

Jeter, the 11 time All-Star, seems to still be going strong, but do the Yankees really need Jeter to succeed?

For the first time in his big league career, Derek Jeter is a free agent. For the time being, he has remained one.

The Yankees captain is looking negotiate a new deal with the only team he has ever known and played for.

This past week, the Yankees submitted their first offer for three years and $45 million, which would earn Jeter $15 million per season.

For a typical 36-year-old shortstop who has had some decline, that would be considered overpaying for the player. But Jeter is not the typical shortstop.

Derek Jeter is a Yankee. Let's get that out of the way before we get to anything else on this list.

The Yanks and Jeter's agent are all talk right now, but there's still lots of wheeling and dealing to be done before the start of spring training, and the Yankee captain is too much of a fan favorite for them to let him get away. 

That being said, there is the slimmest of chances that somehow, someway, Hank and the Steinbrenners screw this thing up. What becomes of the Yankee captain then?

It has been some time since the New York Yankees weren't involved with an offseason's top free agents. This year—to the chagrin of many baseball fans—is no different.  The most prized member of this year's free agent class, lefty Cliff Lee, tops just about every team's free agent priority list. For the Yankees, Lee could quite possibly be the piece that seemed to be missing down the stretch in their 2010 campaign. 

The New York Yankees are going to re-sign Derek Jeter, right? Right? Surely, they'll find some money in their infinite budget to bring back their captain, a guy who has led the team to five World Series Championships.

Though the Yankees will ultimately reach some sort of middle ground with Jeter, keeping him in pinstripes for the rest of his career, they aren't making things easy.

The Yankees' brass has called out Jeter on a couple occasions this offseason, saying his ego is getting in the way and that they won't overpay for a guy who isn't worth as much as he thinks he is.

While 2009 ended with a World Series championship, 2010 ended in disappointment.

While the Texas Rangers celebrated in front of their home crowd and were heading to their first World Series championship in franchise history, the 2010 offseason was beginning for the New York Yankees.

The Yankees and their 200 million dollar payroll, began their offseason earlier than expected.  Now multiple uncertainties surround this team, with some of the greatest players in franchise history becoming free agents.

Derek Jeter is still a free agent, much to the surprise of the entire baseball community.

Jeter's agent, Casey Close, has said that he is "baffled" by the way negotiations are proceeding and how little respect the Yankees organization is showing for their most iconic player.

If you asked me two days ago what I thought would have to happen for Derek Jeter not to re-sign with the Yankees, I'd basically have only three educated guesses:

1) He decided to focus his attention on his new chain of Derek Jeter's Taco Hole restaurants.

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.

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Most of the Hot Stove headlines in Major League Baseball will go to the big-ticket free agents that have landed on the open market. Prudent teams, however, can often make major improvements to their rosters by targeting less-heralded players in free agency.

Given the big-money nature of MLB salaries in the 21st century, it's hard to argue that any free agent signing is a true bargain, but when looking at players from a cost-to-production perspective, second-tier free agents can frequently pay big dividends.