The 5 Biggest Decisions the Boston Red Sox Have to Make This Offseason

The Red Sox are entering a crucial offseason that will determine not only the success of the team for the next few seasons but could be the difference in whether general manager Ben Cherington keeps his job.

While the World Series victory in 2013 obscures all and was representative of brilliant moves by Cherington, the simple fact is that the Red Sox have finished in last place twice in three seasons.

With Boston's vaunted farm system finally paying dividends and massive financial flexibility lying ahead, Cherington has to successfully navigate this winter in order to deliver a perennial contender to Boston. With a gaping hole at the front of the rotation, questions surrounding the future of prospects in town and finding a third baseman, there are five major decisions the Red Sox need to make in order to lay out a plan of attack.

One decision is not rebuilding the bullpen—while it is absolutely an element the club will need to address, the way Boston goes about addressing the bullpen is not crucial to its offseason plan. It will be addressed one way or another, starting with determining the status of incumbent closer Koji Uehara.

Far more important to the team's success this winter is determining how Boston's internal pieces fit into Cherington's vision for 2015 and by what avenues the biggest holes on the Red Sox are to be addressed. 

Decision No. 1: Deciding Which Prospects to Keep

Jim Rogash/Getty Images

Does Boston trade Mookie Betts or any of its other top-flight prospects?

The Red Sox boast two elite prospects who are ready to help at the major league level: shortstop Xander Bogaerts and outfielder Mookie Betts.

The wealth doesn't stop there, though. Boston also has the best catching prospect in the game, Blake Swihart, who is poised to debut at some point in the 2015 season. Furthermore, while the club lacks an elite starting pitching prospect, they have a whole plethora of pitching prospects expected to land in the middle of a rotation in the next few seasons.

As the Red Sox move forward, they need to decide who is untouchable and who is not. If Cherington declines to move Bogaerts, Betts or Swihart, there won't be any blockbuster trades this offseason. The Chris Sales and Giancarlo Stantons of the world will demand one—perhaps two—of these names. Trading will be limited to acquiring complementary players, which will put the onus on a successful outcome in the free-agent market.

What the decision should be: Building around the core three prospects will give the Red Sox superstar production for low cost the next few seasons, freeing up financial resources to fill in around these players. That's a tremendous luxury to have. Keep them.

Decision No. 2: Settling on an Outfield Configuration

Jared Wickerham/Getty Images

Will Yoenis Cespedes be with Boston in 2015?

Boston has a ton of candidates to receive playing time in the outfield.

In center field, Rusney Castillo is the clear favorite to man the position. The Red Sox inked him to a seven-year, $72.5 million deal after the Cuban defected from his country.

Things get hazier after that.

Could Yoenis Cespedes be traded?

Mere months after being acquired in the deal that sent ace Jon Lester to Oakland, there are already rumblings that Cespedes could be on the move again.

As Michael Silverman of the Boston Herald writes, Cespedes could be trade bait in order for Cherington to satisfy more pressing concerns (such as the top of the rotation) and because he may not fit with Boston's philosophy on offense: grinding out at-bats.

There's also Shane Victorino, who missed all but 30 games this past season as he dealt with back problems, outfielder Allen Craig, rookie phenom Mookie Betts and Daniel Nava. Nava was the starting left fielder for much of the 2013 season.

There are too many outfielders for too few spots. While part of the glut could be mitigated by moving Craig to first base, that would mean squeezing out Mike Napoli.

The Red Sox need to figure out the ideal outfield configuration, which will allow them to make better decisions on the trade front.

What the decision should be: Castillo in center field, flanked by Betts in right and Cespedes in left. Craig didn't do himself any favors with his performance after the trade and cannot be counted on. Victorino is too injury prone to rely upon, and Nava is a backup outfielder at this stage of his career. Further, the Red Sox could use the power that Cespedes provides.

Decision No. 3: Selecting Which Pitchers to Target

Jim Rogash/Getty Images

Will Jon Lester return to Boston?

The Red Sox have a gaping hole at the front of their rotation after trading away Lester and Lackey. With no internal options, the first two starters next season for the Red Sox are currently outside the organization.

The Red Sox need to identify their top targets in order to focus all their efforts on walking away with at least one top-of-the-rotation starter. More importantly, they need to determine whether it's feasible to focus on a certain pitcher or if it's a waste of time.

Should Boston even bother trying to bring Lester back? Or did their failed negotiations with the left-hander all season, followed by the trade, essentially close the door? Should anything be read into Lester's home in Newton, Massachusetts, being put up for sale, as NESN points out? With only so much manpower and time, knowing whether Lester is a real possibility to return will help the Red Sox focus their efforts.

Further, what goals do the Red Sox want to accomplish in acquiring starting pitching? Do they want to get quality veterans who can help mentor their young starters? Royals starter James Shields has a reputation for helping to develop young pitchers, as WEEI's Alex Speier writes—will he be their top target in free agency?

Or does Boston want to go younger and acquire pitchers with controllable contracts? That means a deep foray into the trade market.

What the decision should be: Target a top free-agent pitcher (Shields in particular), move on from Lester and try to get an additional pitcher through the trade market such as Johnny Cueto from Cincinnati.

Decision No. 4: Choosing a Third Baseman

Harry How/Getty Images

Could Pablo Sandoval head to Boston?

The decision of choosing a third baseman doesn't necessarily mean the Red Sox need to know right away who their 2015 third baseman will be.

But they do need to know what their plan of attack will be. Is it staying internal and giving Will Middlebrooks a chance? Turning the gig over to prospect Garin Cecchini after an impressive season? Seeing if Brock Holt can sustain a full season of starting?

Or is the answer external? And if it's external, how important is production from third base going to be? Should Boston go hard after Pablo Sandoval, the premier third baseman on the market, or is it better to pursue a secondary option like Chase Headley?

How about the trade market? If Oakland makes Josh Donaldson available, as Fox Sports' Ken Rosenthal theorized could be the case, to what lengths would the Red Sox go to get who would immediately become the most sought-after position player on the block? (Giancarlo Stanton does not count; he is not officially on the block, according to team president Michael Hill per The Associated Press.)

In order to maximize their activity this offseason, the Red Sox need to have a plan of attack for filling their hole at third base. They also need to determine which prospects they will trade, which starting pitchers to target and what their outfield configuration will be.

What the decision should be: The offense was largely addressed through moves made in the offseason and is essentially ready to go. The Red Sox need to pour all their assets into pitching, so a secondary option like Chase Headley makes a lot of sense and gives Boston a chance to see if Middlebrooks can rebound in Triple-A.

Decision No. 5: Picking the No. 5 Starting Pitcher

Al Bello/Getty Images

Can the knuckleballer Steven Wright win the No. 5 spot?

The Red Sox have a whole plethora of options in deciding who their No. 5 pitcher will be. It could be young players such as Rubby De La Rosa, Allen Webster, Anthony Ranaudo, Brandon Workman, Matt Barnes or even 30-year-old Steven Wright.

In fact, Sox fans might get to know Wright's name quickly. Currently, his claim to fame is throwing a knuckleball, but he could very well be a rotation member in 2015. As Speier writes, some officials with the Red Sox felt he was the best starter out of all the players brought up from Triple-A and put in the rotation.

Deciding who your No. 5 starter should be is not exactly a pressing decision, but it does have implications for the offseason. For one, knowing who definitely does not have a shot at the job can free up that player to be traded should another team ask after him. Second, there's a chance that Cherington and the Sox believe none of their internal options fit the bill, in which case planning will have to be done in order to scoop up an option in free agency.

Finally, there are some questions whether some of the options listed above might get a role in the bullpen. As Speier notes, it's entirely possible De La Rosa, Webster and Workman all head to the bullpen. If that came to pass, suddenly the Red Sox's options for who fills the No. 5 spot thin out dramatically, and depth will need to be brought in.

What the decision should be: Boston has no shortage of internal options, and the team needs to see what it has. However, it should not hesitate to make any of its pitchers available and worry about who fills the role in spring training.