Boston Red Sox left field carousel

The Boston Red Sox are still searching for a permanent solution in left field eight years after pushing a superstar out of town.

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Remember when the Boston Red Sox faced the annual dilemma of filling the shortstop position? Ever since the team’s relationship with Nomar Garciaparra soured midway through the 2004 season, the Red Sox struggled to find a suitable long-term replacement, leading to a revolving door at the position that lasted for years.

Then Xander Bogaerts came along. His breakout season in 2015 cemented his status as the shortstop of the present and future, stabilizing a position that had long been in flux. Problem solved.

Except now that problem has merely shifted to left field. The Red Sox have a rich history of filling the position with elite talent, from Ted Williams to Carl Yastrzemski to Jim Rice. They got 7+ seasons of Manny Ramirez in the prime of his career, when he was the most feared right-handed bat in the game. He was an All-Star in every full season that he spent in Boston and helped the team capture a pair of World Series titles.

Then he too was sent packing when the organization tired of Manny being Manny. Ramirez was shipped to the Los Angeles Dodgers prior to the 2008 trade deadline so that the Red Sox could wash their hands of a player they determined had become a problem in the clubhouse. Except his departure opened up an entirely new problem on the field.

Since Ramirez last began a season in Boston, the Red Sox have cycled through a different left fielder on Opening Day in each of the last eight seasons.

Next: 2009-2011

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With Crawford missing the first half of the 2012 season due to injury, Cody Ross spent the majority of his only season in Boston replacing him in left until Crawford returned in July. About a month later, Crawford was sent to the Dodgers in a blockbuster deal that helped Boston shed a quarter of a billion dollars in payroll.

2013 gave us our first glimpse of Jackie Bradley, Jr. His defensive wizardry convinced the Red Sox to give him the left field job to start the season, but he was demoted after hitting .097 in April and spent the next few seasons riding the shuttle between Boston and Pawtucket. It took until late last season for Bradley to finally prove himself enough to lock in a roster spot, but he is now the team’s everyday center fielder.

Jonny Gomes ended up seeing the bulk of the time in left that season. While he played a key role in delivering a World Series title, he was never the solution. His biggest contribution was the chemistry he brought to a clubhouse that desperately needed a makeover in the wake of the toxic Bobby Valentine season. His production was more in line with that of a fourth outfielder, best served in a platoon role.

Next: 2014-Present

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The seldom used Mike Carp got the start in left to open the 2014 season, but would share the role with several others, including Gomes. That is until the trade deadline, when Gomes was part of a package headlined by Jon Lester that brought Yoenis Cespedes to Boston to be the new left fielder. While the Cuban outfielder was selected to the All-Star team for his production with the Oakland Athletics in the first half to the season, the Red Sox weren’t impressed with what they saw after bringing him to Boston. He was supposed to be the power threat they were seeking, but Cespedes hit a mere 5 home runs following the trade and the team was less than enthused by his disappointing on-base percentage and head-scratching defensive decisions.

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Boston let Cespedes depart in free agency and replaced him with Hanley Ramirez, who was signed for his bat without any regard to where they would put him on the field. The experiment of converting him to left field failed miserably, forcing the Red Sox to move him back to the infield, where he will now attempt to learn how to play first base on the fly.

That brings us to 2016, where the Red Sox began the season with Brock Holt in left field. As the team’s lone representative at last year’s All-Star Game, Holt is certainly deserving of an everyday role, but locking him into one position deprives him of the versatility that has always been his greatest asset.

The plan is to use Holt as the primary left fielder against right-handed pitching, with Chris Young serving as the other half of a platoon against lefties. Rusney Castillo will also rotate through the position to allow Holt to fill in as an infielder when needed. That still leaves the Red Sox without an everyday left fielder. While the platoon option is the best choice based on the current construct of the roster, it’s not ideal in the long run.

Next: Will the answer come in free agency?

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Left field is traditionally a spot that teams look to add a power bat, which certainly isn’t the profile that Holt fits. Young has power, but should be used exclusively against lefties. Castillo is starting to look like a career backup. So where to the Red Sox turn to for a solution to their left field problem?

They could go the free agent route, but the list of available left fielders on the market next winter isn’t all that appealing. Cespedes has the opportunity to opt-out of his contract after this season and the new front office may have more interest in him than the old regime that let him go. After all, it was Dave Dombrowski that signed him when he was the GM of the Detroit Tigers in 2015.

Jose Bautista could be an option if the Red Sox are eager for a power bat to replace David Ortiz in the middle of the lineup. He has primarily been a right fielder by trade, but spent time in left earlier in his career. They could also consider shifting Mookie Betts to left to let Bautista take over in right. Only problem with that plan is that Bautista will be 36 when he hits the market, trending toward becoming a full-time DH, and will of course be very expensive.

Free agency simply doesn’t have anyone young and talented enough to become the long-term solution in left field. They could explore the trade market, but it’s a bit early to start predicting which teams will make an impact player available in the offseason.

Part of the problem is that left field isn’t all that deep these days. Last season only eight major league left fielders produced at least 3.0 WAR, while only 12 were above 2.0 WAR. That’s not enough to fill even half the teams in the majors with a quality left fielder capable of being an everyday starter.

Next: The answer could come internally

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Perhaps the best solution will be to fill the position internally. Top outfield prospect Andrew Benintendi has been rapidly rising through the farm system since being selected in the 2015 draft last summer. He’ll begin the year in High-A Salem, but there are those optimistic enough about his potential to foresee him cracking the big league roster by next year.

The 21-year old hit .313/.416/.556 in his first taste of minor league action across two levels last season. He’s a center fielder, but that spot is already taken by Bradley as long as he continues to hit enough to warrant a starting role, while Betts figures to be a more viable option to take over if he doesn’t. That could lead to the Red Sox targeting Benintendi as their left fielder of the future.

While Benintendi may be oozing with potential, he still has a lot to prove in order to work his way on to the major league scene. We may be getting ahead of ourselves in projecting him to make the roster out of camp next season, which means there is a solid chance that the Red Sox will end up using a different left fielder on Opening Day for the 10th straight season.

If the Red Sox can’t find a solution in free agency or on the trade market next winter then Benintendi becomes the next great hope for an answer to their left field problem. If the promising prospect doesn’t pan out then the carousel will continue to spin.

Letting go of Manny was the right decision at the time, but all these years later the Red Sox are still searching for a viable replacement.

Next: David Price will win the Cy Young

It took the Red Sox over a decade to solve the riddle at shortstop, now left field is proving to be an even bigger challenge. Dombrowksi dazzled us with his ability to find solutions for the front of the rotation, bullpen and bench in his first offseason at the helm. Now let’s see if he can solve a puzzle that has left the Red Sox stumped ever since they parted ways with an enigmatic superstar.