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Will Derek Jeter exercise his 2014 player option? Should the Yankees want him to?

This fall, Derek Jeter must choose between a $9.5 million player option and free agency. Which option works better for the Yankees?

The Star-Ledger-USA TODAY Sports

Most people have issues with their bosses. They grumble and groan about their pay, about working conditions, about those overtime hours that are always popping up, about that damned copy machine that never really works right, which management just won't replace.

For most of his life, Derek Jeter never experienced any of that. He and the Yankees have always seemed a match made in heaven, outside of a short period of uncharacteristic sniping back in the late fall in 2010. Having just finished a 10-year, $189 million contract, Jeter, a free agent, expected to still be paid know, Derek Jeter. The Yankees preferred to compensate their captain like a 36-year-old shortstop with declining range, coming off the worst year of his career. Jeter's agent, Casey Close, said some stuff he shouldn't have. Then Brian Cashman said some stuff he shouldn't have. After a tense couple of weeks, the sides compromised on a three-year deal with the possibility of a fourth. Earning $16 million per season the past three years, Jeter now must choose between a $9.5 million 2014 player option and a $3 million buyout. For those of you scoring at home, the option rose from $8 million to $9.5 million thanks to Jeter's 2012 Silver Slugger award.

The 2013 season has been a calamity of misfortune for Jeter. The captain spent last off-season rehabbing a broken ankle suffered in game one of the 2012 ALDS only to break the bone again in spring training, which kept him out until July. Two brief comeback attempts were promptly cut short by leg woes and as he returns to the field for a third time this season, Jeter has to be wondering just how much longer he'll be playing baseball for a living.

An opt-in worth $9.5 million might seem like a no-brainer for a player who'll hit the big four-oh next June, but that may not exactly be the case. With $3 million guaranteed either way, Jeter's really only choosing between another $6.5 million and free agency.

Before the break heard 'round the world last October, Jeter was hardly underperforming his latest contract, no small feat, since he was nearing 37 when he signed it. Jeter finished strong in 2011 to post a 2.0 fWAR, 104 wRC+ year while making the Yankees gobs of money as he pursued his 3,000th career hit. In 2012, he looked even more rejuvenated, batting .316/.362/.429 with a 117 wRC+ and a .347 wOBA. Combine Jeter's not-too-long-ago above-average production with his larger-than-life, face-of-baseball public image, and there may be more than one rival team out there willing to risk more than $6.5 million to employ a first ballot Hall of Famer in perhaps his final season. Even if that team doesn't exist, all Jeter and Close need is for the Yankees to think it might. The pair will once again have plenty of leverage.

What's also uncertain for the Yankees is whether Jeter opting in would be a good thing or a bad thing. Jeter's player option, if accepted, would cost an unsightly $15.5 million toward next year's payroll given the average annual value of what would now be viewed under the CBA as a four-year contract. That won't be an easy figure to manage for a front office seeking desperately to squeeze in under the $189 million luxury tax threshold for 2014 while still fielding a competitive roster. On the other hand, if Jeter opts out, the Yankees are still on the hook for $9 million against the 2014 tax floor due to the $3 million buyout and the now-increased value of the previous three-year deal, some of which the team hasn't been taxed on yet. If Jeter expects to sign a one-year pact for something in the neighborhood of $10 million, the Yankees would be hit with a whopping $19 million charge against the 2014 taxable payroll for a player who may or may not be capable of contributing for a full season. For lack of better phrasing, the Yankees are pretty much screwed either way.

The best option available for both player and club might be for Jeter to opt out and sign on for a one-year 2014 deal with a 2015 player option that would help ease the pain for next season. Jeter could agree to earn $8 mil in 2014 - a $1.5 mil bump over what he'd get by opting in to his existing deal, including the $3 mil buyout - and for his deal to include a league-minimum option for 2015. That way he'd cost just $13.25 million against the luxury tax floor in 2014, and the Yankees would have a little extra wiggle room. Of course Jeter wouldn't actually play for $500K in 2015. He'd either retire or opt out and sign another deal, but by including the option, the Yankees would be able to defer $4.25 mil of his payroll hit for a year, when they presumably won't be as concerned with the now-reset luxury tax - if we're to buy the story that Hal Steinbrenner and Randy Levine are presently selling.

A Jeter-Yankee divorce would be a disaster for everyone. Jeter can't relish the idea of playing in another uniform any more than Yankee brass can stomach the thought of him doing so. The two sides need to work together from the get-go this time around. Frustrating as it must be for Jeter when he thinks about just how much money Alex Rodriguez is still owed, and for how many years, the captain has to be realistic about what he's worth now and what the Yankees can realistically afford. Odds are player and team will put their big boy pants on and figure something out, sooner rather than later. Still, the situation will be something to keep an eye on this off-season, especially as cast in the shadow of project 1-8-9 and its wide-reaching implications.

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