I need to preface this post by saying that I’ve made it abundantly clear that I’m a huge Nick Swisher fan, and assuming he turns in a fourth straight 120-plus wRC+ offensive campaign in pinstripes this coming season, I’d expect the Yankees to look to retain the pending free agent’s services on a multi-year deal. So long as his contract requirements remain within reason, anyway.

By “within reason,” I’d say anywhere from the three-year, $21 million ($7M average annual value) deal personal favorite Josh Willingham signed with the Twins this winter (which still seems like the steal of the offseason) to Michael Cuddyer’s three-year, $31.5 million deal ($10.5 million AAV) with the Rockies. However, since breaking into the league in 2004, Swish has been the superior all-around player by a not insignificant margin, and being that he’ll be two years younger than Cuddyer was this past offseason he definitely has a case for a bigger deal than Cuddyer’s, and a strong case for a bigger contract than Willingham’s sweetheart deal. Between his apparent superiority to these similar players and the fact that this will be his first foray into free agency, I’d expect him to start out at the very least looking for something that will pay him $13 million a year.

Given the incredible value the Yankees have gotten out of Swisher thus far — since 2009, Swish has been paid $21.2 million for his services by the Yankees, and according to FanGraphs’ $/WAR calculation, has been worth $47.6 million — $13 million seems like an eminently reasonable ask; however, at the end of the day I’d expect length to be a bigger sticking point than AAV. As an outfielder coming off his age 31 season next winter, one has to think Swish will be looking for enough financial security to take him as close to the end of his career as possible. I could see his initial ask starting at five years, but I don’t see the Yankees being interested in committing any more than three years to their switch-hitting right fielder. Maybe they’d go to four, but I’m not sure I’d expect the Yankees to hand out a four-plus-year contract to an outfielder on the wrong side of 30 that isn’t named Curtis Granderson, who — barring an unforeseen precipitous decline in production — the team will be looking to re-sign after 2013.

So, in the event that the Yankees and Nick Swisher can’t arrive at a happy medium next winter, the Bombers may in fact be finding themselves in the market for a right fielder. Enter B.J. Upton, slated to be a free agent for the first time in his career next offseason. As an outside observer, it seems as though the Rays have been waiting for Upton — the second overall pick in the 2002 amateur draft — to become the superstar many predicted he’d blossom into forever.

I asked noted Rays fan Jason Collette, of Baseball Prospectus and DRaysBay fame, for some color on this notion, and he was kind enough to respond with the following:

BJ will always leave a portion of this fanbase wanting. There’s a portion of this fanbase that finds Upton to be an unmotivated and lazy waste of talent that the Rays need to move. There’s a portion that is disappointed with him but are holding out hope that 2012 is a lot like 2007. There’s a portion that appreciates him for what he is rather than what he is not. I think he could go 30/30 in Yankee Stadium given his best swings are when he goes the other way, but he is never hitting .300 again without some serious BABIP help. He goes through hot streaks that are really hot and then slumps for long periods at a time while tinkering with his swing. He made some changes with his legkick late in the season over the final 6 weeks that yielded positive results, so it bears watching. There is a level of A.J. Burnett hate with him with a portion of this fanbase that sees nothing wrong with booing him after a strikeout or when he’s thrown out on the basepaths. However, there is a larger portion that will miss him when he leaves and hopes that he does not hang around the American League to blossom as it is tough enough to watch Carl Crawford do the same for Boston. In the end, he always leaves fans wanting something; the degree of that want comes from each fans attitude toward Upton.

Upton was drafted as a shortstop back in ’02, but was an unmitigated disaster at the position, and despite posting a respectable .323 wOBA as a 19-year-old in 177 plate appearances in 2004, his defensive woes helped demote him to AAA Durham for the entirety of the 2005 season. Upton didn’t make it back to the bigs until August 1, 2006, but he struggled mightily (.275 wOBA in 189 PAs) while playing third base, a position he’d never played professionally prior to that season.

At the outset of the 2007 season, Upton was shifted to second base to start the season, with the idea that he could play anywhere from second to short to third to the outfield on any given day. Upton responded to his first camp-breaking with the Rays by exploding out of the gate, posting a .471 wOBA in April 2007, and ultimately finishing the year with a career-high .387 wOBA (138 wRC+), shifting into center field full-time and seemingly finally establishing himself as the offensive force everyone had been waiting for. Only it didn’t last.

Upton followed his monster 2007 with a good (.354 wOBA, 118 wRC+), but disappointing 2008, given the new baseline he’d established the year prior. Upton’s OBP was still monstrous (.383, after .386 in 2007), but his power mysteriously vanished, and his slugging dropped over 100 points to .401. Upton continued his slide in 2009, falling to a below-average .310 wOBA (88 wRC+), which was easily his worst full season in the bigs. Upton has since recovered a decent amount of his value, posting near-identical 2010 (.337 wOBA, 113 wRC+) and 2011 (.337 wOBA, 115 wRC+) campaigns while providing above-average defense in center, though his erratic performances these last several seasons have rendered Upton’s true talent level something of an enigma.

One aspect of Upton’s game that would undoubtedly be very appealing to the Yankees is his ability to draw walks. Upton has a career 11.2% walk rate, well above league average. His career OBP is a respectable .342; however, the reason it’s not higher is because Upton also has a propensity to strike out. A lot. Upton’s career K% is 24.8%, and his 25.2% K% was the fifth-worst in the AL last season. His strikeouts have dramatically suppressed a batting average (career .258) that one would expect to be a good bit higher for someone with a carer BABIP of .327. Upton also has a career 11.3% HR/FB%, also an above-average rate, and the high BABIP and HR/FB% show that when Upton does put a bat on the ball, good things tend to happen. Unfortunately this isn’t as common as an occurrence as one would hope. Perhaps there’s something in Upton’s swing that Kevin Long can fix?

Upton would also probably be the best defensive right fielder the Yankees would hypothetically have fielded since perhaps Raul Mondesi, and an outfield of Brett Gardner, Curtis Granderson and Upton seems like it would be hands-down the finest defensive outfield in the game. The dropoff in offensive production from Swisher to Upton would be fairly substantial, but not massive (Swish is a 117 career wRC+ hitter; Upton 110), while Upton would make a lot of the difference up in fielding.

Upton’s patient/hacker dichotomy — his 3.86 pitches seen per plate appearance (P/PA) ranked 31st in the AL last season, ahead of the likes of Derek Jeter, Jacoby Ellsbury and Adrian Gonzalez, among others, while his swinging strike percentage of 20% that was the 4th-highest in the league, and well above the 15% league average — is somewhat reminiscent of Curtis Granderson’s, although Grandy led the league in P/PA in 2011 and recorded a 16% swinging strike percentage.

Given his abilities I don’t think it’s a stretch to say that the 27-year-old Upton’s (turning 28 in August) best-case-scenario is blossoming into modern-day Curtis Granderson — if you compare the first five years of each player’s career, the results are remarkably similar, with one elite season early on followed by some good — though not great — subsequent campaigns. Upton’s got the edge in OBP, though Granderson certainly has the edge in power. Some may argue that Upton’s running out of time to get there, but his 2007 shows that it’s not crazy to envision him finally putting it all together on a consistent basis as he enters the prime of his career, similar to the way Granderson turned in a career year in his age 30 season.

The parallels between Granderson and Upton become even more apparent when you look at their WAR graphs:

Source: FanGraphs — Curtis Granderson, B.J. Upton

And cumulative by age:

Source: FanGraphs — Curtis Granderson, B.J. Upton

Also, for those curious about the righty Upton’s splits, while he unsurprisingly hits lefties better (career 118 wRC+), he’s playable against righties (101 wRC+).

So after all of this analysis, we haven’t even answered perhaps the most important question — how much will Upton be looking for, and what can he reasonably expect to be offered? Unfortunately for B.J., as a career .339 wOBA hitter, it seems unlikely he’d see anything close to the mega-deal his former teammate Carl Crawford signed prior to the 2011 season, as Carl has been the superior player (not to mention a massive disappointment one year into his monster Boston contract); although to play devil’s advocate, Carl’s career wOBA was only .008 points higher than Upton’s at the time of his free agency, so perhaps I’m selling Upton a bit short. Upton is making $7 million in his final year as a Ray, and will obviously look to exceed that on an annual basis.

With teams seemingly increasingly shy to commit mega dollars and years to anyone outside of elite talent, it seems like a stretch to see anyone signing Upton for longer than five years, and given his erratic offensive play, I’m not sure he’s worth more than $10-$12 million a year (although FanGraphs’ $/WAR valuation has him worth an average of $17.3 million over the last five years).

Upton will probably start out asking for something like seven years and $105 million ($15M AAV), but I’d ultimately expect him to end up signing for something closer to five years, $60 million — which, if the Yanks can’t agree to terms with Swish, should very seriously consider Upton if his price does fall to this range — unless he has another year like 2007 in him in 2012. In that case, all bets are off.