5 Questions The Boston Red Sox Must Answer In Spring Training

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Red Sox Boston Strong

Red Sox Boston Strong
Mark L. Baer-USA TODAY Sports

I am a die-hard Boston Red Sox fan, and watching them win the World Series last season was incredible.

After the Boston Marathon bombing, the Red Sox rallied around the city of Boston, and the city of Boston rallied around the Red Sox. I know the 2004 Red Sox team will always be remembered for the comeback against the hated New York Yankees in the ALCS and for bringing the World Series trophy back to Boston, but the 2013 team may end up being even more memorable. David Ortiz's Grand Slam in Game 2 of the ALCS against the Detroit Tigers and Torii Hunter tumbling over the wall in an effort to catch it as a Boston police officer celebrated was unbelievable. Shane Victorino's Grand Slam in Game 6 of the ALCS and then his triple in Game 6 of the World Series will ensure that Mr. “Three Little Birds” Shane Victorino will forever be loved by the people of Boston.

It was magical to watch the Red Sox run through the postseason en route to their third World Series in 10 years.

If you look at their current roster, the Red Sox lineup would probably look like this when they face righties:

1. Daniel Nava, LF

2. Dustin Pedroia, 2B

3. David Ortiz, DH

4. Mike Napoli, 1B

5. A.J. Pierzynski, C

6. Shane Victorino, RF

7. Xander Bogaerts, SS

8. Will Middlebrooks, 3B

9. Jackie Bradley Jr. or Grady Sizemore, CF

Yes, I’m aware that if Sizemore ends up playing centerfield, he would more than likely hit higher in the lineup than Bradley.

Looking at their roster, the Red Sox do not seem to have a ton of holes that must be filled. That being said, that doesn’t mean the Red Sox don’t have any issues they need to address before the season starts.

Let’s take a look at five questions the Red Sox must answer during Spring Training.

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5. Should The Red Sox Trade One Of Their Starting Pitchers?

Ryan Dempster
Greg M. Cooper-USA TODAY Sports

Some may think the Red Sox should trade away a starting pitcher — maybe Jake Peavy or Ryan Dempster since they have Jon Lester, Clay Buchholz, John Lackey and Felix Doubront on the roster as well. I say DON’T DO IT.

I know it’s cliché to say a team can never have enough pitching, but it is sage advice. It is vitally important that teams have deep pitching throughout the year and quality pitching come playoff time. It would be a huge mistake for the Red Sox to trade any of their starting pitchers. One or more pitchers currently on their staff could end up on the DL (I’m looking at you, Buchholz), and having an extra arm or two for the rotation can only benefit the Red Sox. The Red Sox don’t currently have a big enough need to fill, so they couldn’t get anything vitally important to their roster in return.

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4. What Do The Red Sox Do About Stephen Drew?

Stephen Drew
Jeff Curry-USA TODAY Sports

I like Stephen Drew and so does Red Sox general manager Ben Cherington. The Red Sox made Stephen Drew a $14.1 million qualifying offer, which he rejected and instead opted to test the free-agent market. Drew can still negotiate with the Red Sox, but if he signs with another team, that team will forfeit a first-round draft pick. That is, of course, unless that team has one of the first 11 picks and then the Red Sox would instead get a compensatory pick in next year’s first-year player draft.

Technically, the Red Sox do not need Drew. As the potential lineup on my first slide shows, the Red Sox can play Will Middlebrooks at third base and Xander Bogaerts at short stop. Bogaerts is young (21 years old) and extremely talented, and he was ranked as the second-highest up-and-comer in the game in MLB.com’s 2014 Prospect Watch.

Drew’s offensive output is inconsistent, but I’d love the Red Sox to re-sign him for his sure-handed defense. Would it be a surprise if Drew re-signed with the Red Sox? No. Do I want Drew in a Red Sox uniform for the 2014 season? Yes, as long as it is at right number and now that Drew has no leverage, that just might be possible.

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3. What Kind Of An Extension Should The Red Sox Offer Jon Lester?

Jon Lester
Pool Photo-USA TODAY Sports

Spring Training is probably when the Red Sox will discuss a contract extension with Jon Lester.

Second baseman Dustin Pedroia signed a lucrative deal last season, and when you look at the pitching market, it seems highly likely that Lester would make a higher average annual amount than Pedroia if he tested free agency, but it seems he would be open to giving the Red Sox a little bit of a home town discount. It’s no secret that teams value elite pitching more than elite position players overall. I am more than okay with Lester signing an extension, as long as the number of years is not outrageous.

Lester just turned 30 years old in January, but he has only been on the disabled list once since he battled cancer in 2006 and 2007, and it was only a 15-day DL stint in 2011 because of a shoulder strain. Lester has been durable. If the Red Sox can sign him to a five-year extension, I’m all for it. I just don’t want them to go more than five years.

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2. Should The Red Sox Give David Ortiz The Contract He Wants?

David Ortiz
Jeff Curry-USA TODAY Sports

David Ortiz had a postseason for the ages and was instrumental in helping the Red Sox win the World Series in 2013, but he only has one year left on this current contract. Ortiz has said he’d like to finish his career with the Red Sox, but if he didn’t receive another long-term deal, it would be “time to move on.” Ortiz later stated it’s only a one-year extension that he is looking for.

Ortiz is set to make $15 million in 2014 and if he only wants one more year, the Red Sox should just go ahead and lock him up for 2015 right now. In addition to hitting .309/.395/.564 with 30 homers and 103 RBIs in 2013 and earning World Series MVP honors, Ortiz was an emotional leader. Ortiz gave a memorable and amazing speech to the Fenway faithful after the Boston Marathon bombings and also delivered a mid-game pep talk during Game 4 of the World Series. After his dugout speech, the Red Sox outscored the St. Louis Cardinals 9-3 over the final 22 innings of the World Series.

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1. Who Should Start In Centerfield, Jackie Bradley Jr. Or Grady Sizemore?

Jackie Bradley Jr.
Winslow Townson-USA TODAY Sports

With Jacoby Ellsbury signing with the Evil Empire, I mean the New York Yankees, the Red Sox need to decide who will play centerfield.

Every Red Sox fan was incredibly excited about Jackie Bradley Jr. at the beginning of the 2013 season and then after 37 games, he was sent back to Pawtucket. Bradley Jr. did have a pretty solid season with the Paw Sox, hitting .275 with a .374 on-base percentage and a .469 slugging percentage. In an otherwise quiet offseason, the Red Sox acquired Grady Sizemore, signing him to a one-year deal worth a base salary of only $750,000. Sizemore could earn $6 million with incentives. Sizemore has a tremendous amount of talent, but injuries have plagued him during his career. He played in 33 games in 2010 and 71 games in 2011 and has not played in the Majors since, but he is a three-time All-Star and has four 20/20 seasons along with two Golf Gloves.

Based on what the Red Sox are saying, it appears this job is Bradley's to lose, but will he have trouble living up to the hype again? I would not be surprised if the Red Sox are happy that they have Sizemore on the roster at some point during the season.

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