Boston Red Sox: 5 Factors GM Must Consider Before Buying or Selling

It should be an interesting few weeks before the July 31 trade deadline for the Boston Red Sox.

It will be the first time we get to see new general manager Ben Cherington in action. He is going to have to decide whether to buy or sell, and that will have a big impact on both the short-term and the long-term future of this team.

Will Kevin Youkilis get dealt?

Will Boston add an arm in the starting rotation or in the bullpen?

Will the Red Sox ship off any veterans and decide to go young?

Here are five vital factors that Cherington will have to consider before the anticipated trade deadline.

Which Direction Is Boston Going?

The most important thing that Cherington has to do is determine the direction of this franchise. At this point, Boston doesn’t look like a playoff team, so it would make sense to deal some of the veterans and get some fresh legs in the door.

That might not be what the Red Sox brass wants to do, though, which really is a shame. Several veterans on the roster are really struggling, and calling up a few prospects couldn't make it much worse.

It also wouldn’t hurt to give the minor league system some depth for the future.

Theo Epstein described the team’s win-now mentality and the Red Sox executives as the “monster,” and now it’s Cherington’s job to control that, according to Joe McDonald of ESPNBoston.com.  

The win-now mentality might force Cherington to trade away some of the remaining prospects within the organization’s control to try and make a late push for a playoff spot.

Whatever the direction may be, Cherington needs to figure it out before making any moves towards the July 31 trade deadline.

Is It Will Middlebrooks or Kevin Youkilis at Third Base?

This one kills me the most, and a lot of you have probably heard my opinion on this: Trade Kevin Youkilis.

If you aren’t going to trade him, send Will Middlebrooks to Triple-A Pawtucket. It’s that simple.

This carousel of players rotating from third base to first base to right field can no longer continue. It's killing the value and production of Youkilis, Middlebrooks and even Adrian Gonzalez.

There has to be some team out there that is willing to take on majority of Youkilis’ salary and give Boston something decent in return. Middlebrooks has to be playing every day if they want him to be a superstar in the future.

I cannot fathom Boston not dealing Youkilis, but I’ve seen crazier things happen. I just hope that they don’t ruin the potential All-Star status of Middlebrooks in the meantime.

Figuring out who the third baseman is—in the short term and long term—will be a huge part of Cherington’s strategy for the trade deadline.

Enough with the Shortstops

I’m not sure what Cherington’s obsession is with shortstops, but he just can’t get enough of them.

He already has Mike Aviles as the starting shortstop in Boston. He also has Nick Punto as the backup middle infielder.

In Triple-A, he’s got Jose Iglesias, who could be the future shortstop of the franchise but is currently sidelined with injuries. He also has spring training superstar Pedro Ciriaco playing in Iglesias' absence.

Other notable shortstop prospects include the talented Xander Bogaerts—who could give Iglesias a run for his money—and Jose Vinicio, who still needs times to develop before we can make further judgments.

Then, at the MLB draft, the Red Sox decide to take Arizona State shortstop Deven Marrero with their first-round pick. And if they weren’t comfortable with all of them, Cherington went out and signed Tzu-Wei Lin from Taiwan.

Why all of the shortstops, Cherington?

If there’s one position that they’re deep at, it’s shortstop. There’s no need to go out and get any more.

No. 5 Starter Is Still an Issue

If there’s one spot that Boston should look to add depth to, it’s the starting rotation.

Credit Jon Lester, Josh Beckett, Clay Buchholz and Felix Doubront for making it thus far.

Transitioning Daniel Bard from a reliever into a starter completely backfired, and he is currently in Triple-A trying to figure things out.

Daisuke Matsuzaka, coming off of Tommy John surgery, has made two decent starts, but he is no lock to finish the year in the rotation.

I’ve suggested that Boston pursue Chicago Cubs starter Ryan Dempster. Maybe they get him, and maybe they don’t. My first name is Ben, but my last isn’t Cherington, so I don’t get a say.

Even if it isn’t Dempster, Boston needs someone. Beckett is now scratched for his next start, and manager Bobby Valentine is going to use reliever Franklin Morales instead.

If I’m Cherington, I go into the trade deadline thinking that Bard comes back as a reliever and Matsuzaka is the Matsuzaka of old. 

Injured Players Will Get Healthy

There is an abundance of players on the disabled list at the moment, and many of them are integral pieces of this team.

The three starting outfielders—Jacoby Ellsbury, Carl Crawford and Ryan Kalish—are all making their way back from their respective injuries.

Many players have filled in during their absences and haven’t played too bad. Scott Podsednik, Daniel Nava and Ryan Sweeney are capable of manning the outfield for a few more weeks. Don’t forget about Cody Ross, who could be back soon, either.

Eventually, Andrew Bailey will pitch at Fenway Park. I don’t know when that will be, but it’s going to happen someday.

It would be stupid for Cherington to go and add another outfielder in-season. If he needs an outfielder going forward, go get one in free agency after the season ends.

It also doesn’t make a lot of sense to add to the bullpen, outside of acquiring another left-handed reliever. Rich Hill is out for about a month, and Morales has found himself in the starting rotation due to the Beckett injury. That leaves Andrew Miller as the only left-hander available.

Cherington shouldn’t use current injuries as reasons to make extreme moves.