In four years Derek Jeter‘s last big contract with the Yankees will expire and the Yankees will have to move on. As weird as it will be, life after Jeter will begin, at least at the shortstop position. With all due respect to Cito Culver and Eduardo Nunez, it is likely that Jeter’s eventual replacement is not within the organization as of today. He will either join via the amateur draft, trade or free agency. Fortuitously, the best offensive shortstop in baseball will hit the free agent market the very year Jeter’s contract expires. After spending nearly a decade with the Florida Marlins, Hanley Ramirez will become a free agent as a 30-year-old. Will he find himself fitted for pinstripes?

The Good

While Troy Tulowitzki is quickly creeping up on him, it’s hard to argue with the statement that Hanley Ramirez is the best offensive shortstop in the game. After being traded from Boston to Florida in the Josh Beckett deal, Hanley Ramirez won Rookie of the Year in 2006. As a mere 22-year-old Hanley clubbed 17 home runs and swiped 51 bases and hitting .292/.353/.480. In 2007 he elevated his game even further. He stole 51 bases again but cut down on his strikeouts and hit an incredible 29 home runs. His batting line was an MVP-worthy .332/.386/.562. The Red Sox won the World Series that year, but there had to be an element of regret within the organization to see how rapidly Hanley was becoming a superstar.

In 2008 Ramirez posted an aesthetically pleasing batting line of .301/.400/.540, a step back in power but a step forward in on-base percentage. The following year he again accumulated over 7 fWAR and placed second in MVP voting. His on-base percentage was only 10 points higher than 2008, and his slugging percentage was only three points higher, but he won the batting title with a .342 average. Hanley’s always been a high BABIP guy (.347 career average) but his .379 mark in 2009 was a new high for him.

In 2010 his game took a step back. He only hit 22 home runs, a low for him since 2006, and his on-base and power skills dipped slightly as well. This was probably related to his ground ball rate. He’s a career 44% ground ball hitter, but hit ground balls at a 51% clip in 2010; this increase came largely at the expense of fly balls. Whether this was a momentary blip or a sign of things to come remains to be seen. It is worth noting that Ramirez battled and elbow injury for a lot of the season.

Regardless of the 2010 blip, Hanley Ramirez has been the model of offensive production in the past four years. Cumulatively, it’s nearly impossible to find a more productive shortstop over the past four years. He hit 107 home runs, most of any shortstop. He’s stolen 145 bases, second to only Jose Reyes. His ISOp is .213, tied for highest with Troy Tulowitzki. He has the highest batting average (.319), on-base percentage (.394) and slugging percentage (.532) and wOBA (.400). In the past four years, he’s had the the highest wOBA for a shortstop in three out of the past four years. At some point, the superlatives become repetitive. Hanley Ramirez can hit. He can really, really hit.

The Bad

One of the biggest knock on Hanley is his defense. He’s a big guy, and doesn’t really grade out positively by any defensive metric. Over at Fangraphs just six weeks ago Joe Pawlikowski wrote up different players who saw their fWAR knocked down by the defensive component. Ramirez featured prominently:

Defense was the major knock on Ramirez from the moment he started in the majors. In his first two years in the league he had UZRs of -9.3 and -20.5. He followed that up with two mostly average years, which provided some hope that he could remain at shortstop while hitting like a right fielder. Both ideas came crashing down in 2010.

Not only was Hanley’s 25.4 RAA his worst mark since his rookie campaign, but his UZR was in the negative double digits. The combination caused quite a dip in his WAR.

Saving Grace: TZL isn’t nearly as down on Hanley, pegging him at -5 for the year and 8.8 — in the positives! — for his career. DRS, on the other hand, mostly agrees with UZR, except it’s a bit more pessimistic.

All told, it’s hard to find anyone who would argue that Hanley is a plus defender. His single-season UZR is going to fluctuate year-to-year, just like a BABIP is going to fluctuate in the first third of a season, but scouting and most defensive metrics agree that his fielding is subpar. As he ages and loses some of his quickness, it wouldn’t be a surprise to see him move off the position. Some expect him to wind up at third base; right field could be another destination.

The element of downside risk with Hanley is the perceived attitude issue. A lot of this stems from the blowup he had with his manager Fredi Gonzalez on May 18. After fouling a ball off his shin in the first inning, Hanley took the field in the second inning. With runners on first and second, Tony Abreu blooped a ball over his head into shallow left field. Ramirez couldn’t get to it, and when reaching down to field it with his glove he accidentally kicked it with his left foot, sending the ball 100 feet away into the left field corner. He then slowly jogged after it, allowing two players to score and Abreu to advance all the way to third base. Now, Ramirez did seem to have a slight limp and it is possible that his shin pain was severe. Regardless, he moved rather slowly after the ball. The video is a bit shocking. It’s rare to see a player pursue a ball like that. It’s as if the play was already dead. Manager Fredi Gonzalez was angry, and pulled Hanley out of the game. Hanley sat out the next game, and openly criticized Gonzalez:

“It’s his team. He can do whatever,” Ramirez said, mixing in an expletive. “There’s nothing I can do about it.” “That’s OK. He doesn’t understand that. He never played in the big leagues,” he said.

Unfortunately Gonzalez didn’t survive the year, getting fired in the end of June. He moved on to greener pastures in Atlanta, but the perception that ownership sided with the superstar rather than the manager lingers. The fact that Loria had given Ramirez a diamond-studded necklace to celebrate his batting title championship a year prior doesn’t exactly help to dispel that myth. Yet, the most important question is whether this will be something that promises to cause trouble in the future. For what it’s worth, Hanley has been talking a big game this spring, saying that he was very disappointed in his 2010 production and promising a whole new level of effort. His 2010 issues could just be a blip in the radar; the proof will be in the pudding.

The Money

By the end of the 2014 season the Yankees will get some serious salary relief. After the 2011 season Jorge Posada‘s $13M will come off the books. After 2012 Rivera’s salary ($15M) comes off the books, although it’s possible that he could re-up on another 1 year deal for the same salary. AJ Burnett’s $82.5M contract expires after 2013 as well. After 2014, Derek Jeter’s contact expires.

As of present, the Yankees have about $69M committed to the 2015 payroll. Of course, this doesn’t include a potential deal for Nick Swisher or his right field replacement (free agent after 2012), Phil Hughes, Robinson Cano or Curtis Granderson (free agents after 2013) or the various holes in the pitching rotation. The Yankees will be shelling out some serious coin well before Cashman ever sits down at the negotiating table with Hanley and his agent Andy Mota. They’ll also have a very big hole at shortstop.

As a 30-year-old, Ramirez will likely be seeking one very big, very long contract. Provided he continues his prodigious offensive production and stays at shortstop, it wouldn’t be surprising to see him seek a deal for at least 8 years. Even if he’s moved off shortstop to third base, his offensive production would still put him among the elite third basemen in the league. All told, there’s a lot that can happen between now and the 2014-15 offseason. Loria could open up the purse strings and make Hanley a Miami Marlin for life, or the Yankees could draft a viable replacement for Jeter at shortstop. The Yankees have handed out their fair share of big contracts in the past. Whether they’ll be able to resist the siren’s call again with Hanley will be a fascinating situation to monitor.