It’s easy to forget that Jacoby Ellsbury only played in eighteen games two years ago. It’s easy to forget that in his last full season before 2011, his defense cost the Red Sox runs. It’s easy to forget that many, including Kevin Youkilis, questioned his toughness. In simple terms, it’s easy to forget that some people believed he’d never return to the elite status he displayed during the 2007 World Series.

Jacoby Ellsbury’s 2011 season will not be forgotten.

Boston’s center fielder went from being a question mark to being second place in the American League Most Valuable Player voting. He led the American League in WAR, he jacked 32 home runs (21 more than his previous total in a season), and on top of all this, he stole 39 bases. All in all not a bad season.

The problem that now presents itself is this: Jacoby Ellsbury may be hitting his way out a Red Sox uniform before our eyes. With only two years left before he can hit free agency, and Scott Boras looming in the wings, Boston fans will have no choice but to watch as the mega-contracts for Ellsbury roll in.

To begin with, Ellsbury is a rare specimen. He’s batted leadoff for the Sox since 2008, but in all realities, he should probably be hitting third. One of his only weaknesses has always been his inability to take walks, something that should be a leadoff’s man greatest strength. Maybe it was because Boston really didn’t have a better option for the last three years, or maybe it was just the blazing speed that kept Ellsbury at the top of the order, either way it’s not the spot best suited for him.

The point is, when you think of monster contracts, ones that reach into the mid to high 100 million range, a leadoff man isn’t the prototypical player that comes to mind. Slugging first baseman and outfielders seem to be more suited for this type of money, at least in the past. As the game and the philosophies of front offices evolve, there has been a trend towards a new type of value, one that does not rely solely on home runs and RBI’s, but instead takes things like elite defense, speed, and run production into account. Look no further than the contract handed out to leadoff man Jose Reyes this offseason. Or, *gulp*, the Carl Crawford deal last winter.

The truth is that in most major league lineups, Ellsbury would be batting third. Having him at leadoff is a luxury (well, depending on who you talk too.) It will be interesting to see what Bobby Valentine does with the order this season. It wouldn’t be surprising to see Carl Crawford at leadoff, Dustin Pedroia in his customary two-hole, with Ellsbury third and Gonzalez hitting cleanup. Just the fact that this option could be in play shows that Ellsbury has entered a new, elite, level.

Ellsbury only made 2.4 million dollars last year. Entering his first year of arbitration, he stands to make a major raise. The question is, how large will the raise be? By Fangraphs.com measurement, Ellsbury was worth 42.5 million dollars last year. Just a bit of a discrepancy. How much Cherington offers Ellsbury before arbitration could be indicative of how the negotiations between the two sides will play out over the next two years.

Ellsbury is represented by Scott Boras, and it certainly doesn’t take a whole lot of explanation to figure out what that means. He’s going to test free agency. Unless Boston counters with an absolute Godfather deal, there’s absolutely no scenario where Ellsbury resigns before testing the market. Boras does this with almost all his clients, and Ellsbury will be no different.

Perhaps the most painful thing to think about is the fact that it could be Carl Crawford that keeps Ellsbury from staying in Boston. His 142 million dollar contract was the highest amount ever given to an outfielder who had never hit more than twenty home runs in a season, and that’s certainly not a mark he exceeded last season. While everyone expects Crawford to improve, it’s hard to fathom ever putting up the numbers that Ellsbury did last season. With over 18 million dollars due to him per year over the next six years, one has to wonder whether Boston has the money to invest so heavily in two outfielders. Don’t forget that along with Crawford, they locked up Adrian Gonzalez for the next six seasons last year. The Red Sox have their two corner stone players in place for the next six years, and right now it doesn’t look like Jacoby Ellsbury will be one of them.

Then again, we’ve seen how frugal the front office has been this offseason. Yes, this is mostly because they want to stay under the luxury tax, but at the same time, Ben Cherington seems committed to not locking up any more long-term contracts than the ones that are already in place. Maybe this is because he’s preparing to extend the other key players on the club now. And if so, Ellsbury is obviously one of those guys. If not, well, it’s sad to say but Boston fans may want to start rooting for a regression in Ellsbury’s performance over the next two years, because if he continues along the path that he’s on, he’s going to doing it for somebody else come 2014.