Boston Red Sox: Why the Outfield Could Be Ben Cherington's Toughest Test

Adam MacDonaldAnalyst IIJanuary 28, 2012

BOSTON, MA - SEPTEMBER 14:  Carl Crawford #13 (L), Jacoby Ellsbury #2, and Darnell McDonald #54 (R) of the Boston Red Sox stand in the outfield in the sixth inning against the Toronto Blue Jays at Fenway Park on September 14, 2011 in Boston, Massachusetts. The Blue Jays won the game 5-4.(Photo by Darren McCollester/Getty Images)
Darren McCollester/Getty Images

By all standard and traditional measurements, Theo Epstein brought great success to the Boston Red Sox.

In his nine seasons with the club, the Sox made the playoffs six times. They won the AL East for the first time in over a decade in 2007, reached the ALCS four times and won the World Series twice, ending an 86-year title drought. Under Epstein, Boston averaged over 93 wins a season, after averaging 86 for the previous decade (not counting the strike-shortened 1994 season).

But as we were often told under Epstein, traditional metrics are bad. He didn’t want players evaluated by their RBI and home runs; we won’t evaluate him by his rings. The casual observer would think Theo had a great run as GM in Boston and would be loved by Red Sox Nation. One need only look to Chicago Cubs fans’ euphoria when he left Fenway for Wrigley to see that’s true. But most Sox fans hesitate before singing Epstein’s praises.

Names like Edgar Renteria, John Lackey, J.D. Drew, Eric Gagne, Julio Lugo and Daisuke Matsuzaka haunt Sox fans. They still remember Theo’s gorilla suit. The revolving door at shortstop and free-agency failures came to define Theo Epstein’s tenure as Sox GM.

After the fire sale that was the 2011 offseason, Boston has a new man at the helm in Ben Cherington, but the New Hampshire native inherits a less-than-perfect team.

Starting pitching is a major worry, the team’s legendary designated hitter remains unsigned, the bullpen is full of question marks, there is still no full-time shortstop, they have a platoon in right field, the left fielder might miss the start of the season and the third baseman is a serious injury concern.

TORONTO, CANADA - SEPTEMBER 8:  Jacoby Ellsbury #2 of the Boston Red Sox slides safe past J.P. Arencibia #9 of the Toronto Blue Jays during MLB action at the Rogers Centre September 8, 2011 in Toronto, Ontario, Canada. (Photo by Abelimages/Getty Images)
Abelimages/Getty Images

A lot of these have short-term fixes. Nick Punto and Mike Aviles could provide a decent option at short. David Ortiz has an arbitration hearing, Carl Crawford doesn’t have a serious injury and they have movable pieces in both the rotation and pen.

However, the situation in the outfield is such that, in a few years from now, it could go so spectacularly wrong it becomes the mark of failure forever attached to Cherington’s reign as GM.

Let’s go right to left. The departure of fan favourite J.D. Drew has left the cavernous right field in limbo. Cherington has no perfect in-house solution, so he has had to shop around in a bad free-agent market. The two best options in the organisation when Ben became GM, Ryan Kalish and Josh Reddick, both had downsides.

Kalish is battling a right shoulder injury that forced him to miss almost the entire 2011 season and led to two surgeries. Reddick played at the major-league level a fair bit over the last few years but often struggled—the Sox traded him to Oakland for Andrew Bailey.

With their best option injured and their second-best option playing in California, the Sox have to turn to Darnell McDonald, Mike Aviles and offseason acquisitions Ryan Sweeney and Cody Ross. The latter looks to be the favourite to start in right on Opening Day, but his .240 batting average with the Giants last season is nothing to be excited about.

Theo Epstein was GM for nine years, and when he left, he still hadn’t found a regular shortstop. Right field could pose the same problem for Ben Cherington if Kalish doesn’t rebound from his injury.

In center field, the Sox are all set for the moment. Jacoby Ellsbury had a phenomenal season in 2011, rebounding from an injury-plagued 2010 to bat .321, hit 32 home runs, drive in 105 and steal 39 bases. Boston has him under control for the next two seasons; he will become a free agent in 2013. If he replicates or comes close to replicating his 2012 success, he will be one of the most valuable free agents on the market, and able to command a contract in the seven-year, $150 million range.

BOSTON, MA - AUGUST 06:  Jacoby Ellsbury #2 of the Boston Red Sox is congratulated by teammate Carl Crawford after Ellsbury hit a 3 run homer in the fourth inning against the New York Yankees on August 6, 2011 at Fenway Park in Boston, Massachusetts.  (Ph
Elsa/Getty Images

Boston will have four players making over $15 million and two making over $20 million when he reaches free agency. They will also have to consider that in the two seasons after that, Dustin Pedroia, Jon Lester and Clay Buchholz will all see their contracts expire. The Red Sox can’t re-sign everyone, and there’s a good chance Ellsbury will be playing somewhere else in 2014.

The Sox at least have stability at left that they don’t have anywhere else in the outfield. Carl Crawford will be with the team until 2017 and will pocket $20 million a year for the privilege. That shouldn’t be a problem, but so dire was his 2011 campaign that it very well could be.

Crawford hit .255 with 11 home runs, 65 RBI and just 18 stolen bases. He might turn it around in 2012 as he becomes more acquainted with life in Boston, but there are worrying signs for the back end of his deal. His speed is so crucial to his game that age will catch up to his stats fast. Once he slows down a little, his numbers will fall off a lot. He spent so long on the harsh turf of Tampa, and now he has a wrist injury. It might be making a mountain out of a molehill, but there’s a good chance you won’t be getting much production from Crawford in the latter half of his contract.

What are we looking at then? This season the Sox have a questionable and injured left fielder, an MVP-calibre center fielder and a weak platoon in right. In two years time, it could look a lot worse. The smart money is on Carl Crawford not being productive by the time 2014 comes around, Jacoby Ellsbury will probably be gone, and it’s up to Ben Cherington to find someone decent to play right.

If you’re a Red Sox fan, the outfield should worry you. Any problems will be averted with finding the money for Ellsbury and a RF or by making two savvy acquisitions. Cherington may be more capable than Theo Epstein ever was of making good decisions with free agents—but until he proves it, the outfield is a source of concern.