As we draw closer to one of the most exciting dates in the Major League Baseball season, July 31st, speculation continues to increase about the potential availability of some of the game’s most notable players. Included in this discussion is Red Sox outfielder Jacoby Ellsbury, who, by virtue of the team’s current situation, may or may not be a candidate to be moved to another club. It remains unknown whether or not Ellsbury is actually on the proverbial trading block, but for the next twenty three days, his name will continue to be floated in blockbuster trade rumors involving the Red Sox, who are facing quite the uphill battle to earn a playoff spot. In fact, those rumors have already started to fly, as Nick Cafardo of the Boston Globe has hinted at a scenario in which the Red Sox could package Ellsbury and pitcher Jon Lester in a trade for Mariners ace Felix Hernandez.

Now, before you jump through the roof, Cafardo prefaced that particular “rumor” by stating that the Mariners have no intention of moving Hernandez, and it is assumed that he was just generating an intriguing idea for his readers to chew on. However, the thought of moving Ellsbury has crossed the minds of many members of Red Sox Nation, who have probably wondered the following: will the Red Sox indeed look to move the 2011 AL MVP candidate? If so, will they attempt to do so now, or will they wait until the Winter Meetings? And finally, the biggest question of them all, what type of return could the team expect to get from an Ellsbury trade? While nobody other than Ben Cherington can answer that series of questions right now, that doesn’t preclude us from contemplating the issue ourselves.

When it comes to trading a player as notable as Jacoby Ellsbury, one must seriously weigh the pros and cons, the risk versus the reward. Let us first consider potential reasons why an Ellsbury trade would make sense. Right off the bat, it comes to mind that Jacoby is a Scott Boras client, making it very likely that he will look for a serious payday once he reaches free agency after the 2013 season. Baseball fans who have gotten to know the tendencies of Boras over the years are aware that he does a great job for his clients, but often alienates his clients’ employers in doing so. Boras loves to play teams against one another to raise a player’s price tag, and often conjures up creative reports to help convince someone to pay the hefty sum he’s looking for. For that reason, it is quite commonplace for players represented by Scott Boras to test the waters of free agency, rather than negotiating team-friendly extensions prior to reaching the market. Expect this trend to continue with Ellsbury, who most likely hired Boras strictly for this purpose.

Another factor to consider in this case is the current surplus of outfielders on the Red Sox’ forty man roster. In addition to Ellsbury, the team has Carl Crawford, Ryan Kalish, Cody Ross, Daniel Nava, Ryan Sweeney, Brent Lillibridge, and Scott Podsednik who will all be contending for playing time in the near future. The first shoe to drop was Darnell McDonald, who was recently waived and subsequently claimed by the New York Yankees. Kalish, who still has minor league options at this stage of his career, was recently sent down to accommodate the activation of Sweeney from the disabled list. However, with Ellsbury and Crawford due to be activated shortly following the All-Star break, two more spots will be needed. Cody Ross and Ryan Sweeney, who have been major contributors to the team at the plate and in the field in 2012, are essentially locks to remain on the roster. That would leave the team with the four outfielders it envisioned itself having all season back in March: Ellsbury, Crawford, Ross, and Sweeney.

So, what becomes of Daniel Nava, Brent Lillibridge, and Scott Podsednik? Nava, who has given the Red Sox offense a real jolt since his recall in mid-May, will probably be another odd man out with reinforcements on the way. However, he does have one minor league option remaining, so the team is able to send him back to Pawtucket without the threat of losing him to other teams. If the team does indeed wind up moving Ellsbury, the door would then be opened for Nava’s permanent return to the majors.

The decision is much more lucid with Brent Lillibridge. Lillibridge, a utility player acquired in the Kevin Youkilis trade, would be a rather easy player to designate for assignment. Sure, it would make the Youkilis deal look much worse than it already does, but keeping a second player similar to Nick Punto on the roster solely to justify a trade is counterproductive. Lillibridge (or Punto) are easy subtractions from the team in the near future, regardless of Ellsbury’s fate.

Finally, we come to Podsednik, who surprised everyone with his .387 batting average in nineteen games after being acquired from the Phillies organization in late May. The team obviously won’t use that as a reason to deal Ellsbury, but the fact remains that Podsednik could certainly take over in center field if a trade were to occur. For the time being, Podsednik will be in Pawtucket, as he was activated from the disabled list and optioned to AAA two days ago. While replacing the ever popular Ellsbury with thirty-six year old Podsednik wouldn’t make the “Pink Hats” happy, it could certainly be a possibility if the Red Sox decide to use Ells to upgrade in other areas.

Getting back on track, let’s revisit another reason why Ellsbury could indeed be moved. It’s no secret that when Theo Epstein bolted from Yawkey Way to Wrigley Field, he left behind a few sizable contracts, none of which are close to coming off the books. These contracts, most notably those belonging to Carl Crawford, Adrian Gonzalez, and John Lackey, have contributed to the Red Sox approaching the luxury tax threshold, and have put to rest any theories that the team has plenty of money to spend over the next few winters. The financial commitments made to these players has made them highly unlikely to be traded, and has made it just as unlikely that the team can afford to make a similar commitment to Ellsbury going forward.

As we mentioned earlier, it is extremely likely that Ellsbury will be looking for top dollar after the 2013 season, which is something the Red Sox probably won’t be able to afford. At face value, it therefore makes sense for the team to try and move him, whether it’s now or in the offseason. The chances of persuading another Major League team to absorb the contracts of Crawford, Gonzalez, and Lackey are slim to none, leaving the Red Sox with little to no financial flexibility. So, rather than losing your star outfielder for nothing after 2013, it makes a great deal of sense to acquire established talent for him while his value is high. Ellsbury’s trade value will plummet significantly if he is made available as a deadline rental in 2013, so if the Red Sox do intend to make a deal, they must strike while the iron is hot. Conversely, if the team chooses to retain Ellsbury for the duration of his contract and he then leaves through free agency, the compensation will be “sandwich” draft picks, which have proven to be more hit or miss than a package of established players or prospects. All factors considered, it just seems to make more sense to trade Ellsbury now than it does to keep him around a while longer, delaying what seems to be an inevitable departure.

However, like every argument, there is another side to this issue. Although there are reasons why the Red Sox should indeed trade Jacoby Ellsbury, there are also motives for the team to keep him. First of all, are we sure if General Managers of other Major League teams hold Ellsbury to as high of a standard as the Red Sox do? Your immediate answer may be a resounding ‘yes,’ but let’s ponder the matter for a moment, shall we? Despite an unforgettable 2011 season in which he finished as the AL MVP runner-up, Ellsbury’s recent injury history does raise some red flags. Due to the fact that the outfielder has missed 225 games over the last three years, whatever value he does have now is based more on reputation than on results. Out of the other twenty-nine teams in baseball, there may be one or two willing to take the gamble, banking on Ellsbury being more the player they saw in 2011 than the one they’ve seen in 2010 and 2012. However, it is unknown whether they would be too keen on paying a price that much more valuable than what the Red Sox could recoup with compensatory draft picks when Ellsbury walks after 2013. And, despite the fact that compensatory picks are always a wild card, they have been fruitful for teams in the past, notably the Red Sox.

Although Major League Baseball’s entry draft is a total crapshoot, it is unwise to undervalue compensatory picks. After all, these picks have brought a great deal of solid ballplayers to the Red Sox’ farm system over the past few years, including: Jackie Bradley, Jr. (2011), Bryce Brentz (2010), Anthony Ranaudo (2010), Clay Buchholz (2005), Jed Lowrie (2005), and Michael Bowden (2005). Out of the players on that list, only Lowrie and Buchholz have gone on to make valuable contributions to the Red Sox, although Bradley and Ranaudo appear to be on the fast track to success as well. The overall point in this instance is that compensation picks, if used correctly, could wind up netting the Red Sox the next Jacoby Ellsbury, and should not be held in low esteem by any means. So, unless the Red Sox were to receive two first round caliber players in exchange for Ellsbury, there is really no way to justify trading him.

Of course, with Ellsbury set to be activated from the disabled list on Friday after missing nearly eighty games, the window for him to prove his worth to potential suitors is quite small. If he is unable to get back on the field and perform consistently from now until the trading deadline, very few teams will trust his health, and fewer will be willing to gamble on acquiring him. This would end all hope of a trade, which would be a blessing in disguise. Why? Because although the Red Sox have a logjam in their outfield, Ellsbury, despite all the knocks against him, is one of the best players on the team when healthy. It appears to be a real “damned if you do, damned if you don’t” scenario, because if the Front Office has any hope of making the postseason this year, it’s foolish to trade away a player as dynamic as Ellsbury. On the other hand, it’s tough to argue trading such a player when his value is so low.

One final factor to consider is that the Red Sox are not the only team wary of dealing with Scott Boras. Despite those who think he’s bad for the game of baseball, he is a reality and, for his many clients, a necessity. Any argument made about dealing one of his clients in order to avoid negotiating with him will be countered with the obvious fact that other teams feel the same way. It is the assumption of some that Ellsbury’s inevitable flight to free agency as a Boras client is a major reason why the Red Sox should trade him. If this is the case, however, then most other teams will want to avoid that same fate. This will suppress his value, as well as the potential return for him in a trade, because Boras is going to take Ellsbury to free agency no matter what team he’s with when the time comes. Because of this, the only teams that would be willing to trade for Ellsbury are teams in reach of the playoffs who are also desperate for outfielders. Sound familiar? That description pretty much sums up your 2012 Boston Red Sox, which is why the best move in this case may be not making one. In the end, there is no definitive answer as to whether the Red Sox should indeed trade their star centerfielder. However, for the next couple of weeks, the subject will certainly be on our minds.

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