Time’s Up For Red Sox General Manager Ben Cherington

The Boston Red Sox decided that it was time to give the reins of the organization to a new man. Red Sox General Manager Ben Cherington will be moving on after helping Dave Dombrowski find his new office. Brandon Magee takes a look at the tenure of Cherington in one of the most coveted jobs in baseball.

The news quickly spread throughout Red Sox Nation ‒ Dave Dombrowski had been hired as the Boston Red Sox President of Baseball Operations. General Manager Ben Cherington was out, but would finish up the season before leaving for different pastures. For most, the news was received with great pleasure. After all, consecutive last place finishes in the AL East is not just unfortunate, it is unacceptable for a team with the resources and ambitions of the Red Sox. Seeing the head of Ben Cherington roll has been the goal for many, a fresh start with a fresh perspective. 

At the end of his tenure, questions remain: Who was Cherington as a General Manager? Did circumstances conspire to bring his reign down prematurely?

Cherington was named General Manager of the Boston Red Sox for the second time – he was briefly co-General Manager with Jed Hoyer in 2005 after Theo Epstein left the organization in a gorilla suit – in October of 2011.

Inheriting a toxic situation ‒ with both Theo Epstein and Terry Francona exiting stage left and the scourge of “chicken and beer” tarnishing the reputation of refined clubhouses everywhere ‒ Cherington was tasked with rebuilding a broken organization.

Task #1: Find a manager.

Cherington conducted a seemingly thorough search, vetting Pete Mackanin, Dale Sveum, Gene Lamont, Torey Lovullo and Sandy Alomar Jr. and coming to the decision that Sveum was his man. It was not the choice of his bosses however, and Sveum was hired by Epstein to manage the Chicago Cubs. Later that month, the new manager was announced. Bobby Valentine ‒ out of Major League Baseball for a decade ‒ was  the new Red Sox manager. Overruled on his first major decision, Cherington’s reign was off to a rough beginning.

2012 was an unmitigated mess. Sitting at 53-51 at the August trade deadline, the Red Sox were still in position to make a run for the playoffs. But, August was not kind. On August 24th, the Red Sox defeated the Kansas City Royals 4-3, to bring their record to 60-66. And then Cherington shook the baseball world.

In a waiver wire trade that still reverberates, Cherington shed the contracts of Adrian Gonzalez, Carl Crawford, Josh Beckett and Nick Punto for James Loney and multiple prospects – Allen Webster, Rubby De La Rosa, Jerry Sands and Ivan De Jesus. Predictably, the Red Sox ‒ who were in fourth place in the AL East at the time of the trade ‒ nose dived, winning only nine of the final 36 games on the schedule. After a 90 loss season, Valentine was mercifully returned to the wild.

Finally, the organization was able to extract the man they had truly wanted the year before, former pitching coach and manager of the Toronto Blue Jays, John Farrell. 

Cherington quickly started the work of rebuilding the Boston Red Sox: re-signing David Ortiz in early November and picking up catcher David Ross in the middle of that month. Jonny Gomes was signed on the first day of December, Koji Uehara, Stephen Drew and Shane Victorino were inked in the middle of the month, and Joel Hanrahan and Brock Holt acquired via a Boxing Day trade with the Pittsburgh Pirates. None of these signings were greeted with fanfare, instead considered as restocking a decimated roster. As the calendar changed to 2013 and after prolonged negotiations, Cherington finally signed the first baseman to replace Adrian Gonzalez, getting free agent Mike Napoli’s signature on a one year contract.

The team burst out of the gate, ending April in first place in the AL East at 18-8 and never slowed down ‒ never losing more than three games at any point during the season. Cherington made one major move at the trade deadline, moving Jose Iglesias to the Detroit Tigers in a three-team trade while receiving pitcher Jake Peavy from the Chicago White Sox. A minor trade for Quintin Berry in August solidified the playoff roster, and the team rolled through the playoffs, winning their third World Championship in ten years. Cherington was riding high.

Coming off a Championship season, the Red Sox did not do much tinkering with the core. Jackie Bradley Jr., after a fine season for the Pawtucket Red Sox, was given the task of replacing Jacoby Ellsbury who signed with the New York Yankees as a free agent. Playoff hero Xander Bogaerts would take over shortstop. Mike Napoli was re-signed for two more seasons. The peripatetic Grady Sizemore came aboard as outfield depth and Bradley insurance, while Burke Badenhop was acquired for some extra bullpen help. A.J. Pierzynski was brought in to replace Jarrod Saltalamacchia as the catcher whose name no one can spell. But the core ‒ Pedroia, Ortiz, Victorino, Gomes, Buchholz, Lester, Lackey, Peavy, Uehara, and Tazawa ‒ stayed the same. And why wouldn’t it? The team was coming off a World Championship.

Unfortunately, baseball can be a fickle mistress. All the things that seemed to go right in 2013 went wrong in 2014. Shane Victorino and his Gold Glove played all of 30 games due to injury. Will Middlebrooks, who had put up solid enough numbers before Bogaerts took over down the stretch, lost his only real value, hitting just a pair of home runs in 63 games. Bogaerts struggled to adjust to the league, and their advance scouting, in his first full season. Bradley, Jr. couldn’t hit. Drew was brought back after failing to sign anywhere else… and he too couldn’t hit. Buchholz couldn’t keep people off the bases or the ball in the yard. Brandon Workman’s transition from the bullpen to the starting rotation led to a 1-10 record.

As baseball hit the all-star break, the Red Sox were 43-52, 9 ½ games back in the AL East. They made a small move during that break, releasing Pierzynski, but  after a five game losing streak culminating on July 26, Cherington started to trade away pieces. Peavy was the first to go (for pitching prospects Edwin Escobar and Heath Hembree). Felix Doubront went on the 30th and then on the 31st, John Lackey, Jon Lester, Andrew Miller, Gomes and Drew all were sent packing, with the Red Sox picking up Kelly Johnson, Allen Craig, Joe Kelly, Yoenis Cespedes and Eduardo Rodriguez.

It didn’t help. 12 games under .500 at the trade deadline, the Red Sox limped to a 23-31 record down the stretch, going from last to first to last again in a span of three seasons.

However, both last place seasons could at least, in part, be considered part of the plan. The 2012 “Punto Trade” cleared up an inflexible payroll. Without that seismic shift, the Red Sox could not have made the free agent signings that made 2013 possible. In 2014, Peavy, Lester, Miller, Gomes and Drew were all impending free agents. Lackey was looking at a contract that paid him only a minimum salary and was not happy. Trading these pieces for prospects and more controllable assets made sense. But the moves were not made for the present and the team’s record suffered. Without the trades, the 2012 and 2014 teams don’t end up in last place. But, 2013 wouldn’t have happened either.

Back to work in the off-season, Cherington quickly signed Hanley Ramirez to patrol left field and Pablo Sandoval to take over third base. Starting pitcher Rick Porcello was acquired from Detroit for outfielder Yoenis Cespedes. Wade Miley was acquired the next day from the Arizona Diamondbacks for Rubby de la Rosa and Allen Webster. The Red Sox then picked up catcher Ryan Hanigan from the San Diego Padres for the contact-less third baseman Will Middlebrooks. The roster was taking shape, and while the rotation seemed to lack an ace, more than a few experts predicted a resurgence for the Red Sox.

The season has been disastrous, arguably worse than 2012’s Valentine debacle. The fickle finger of fate decided to punish the Red Sox once again: Ortiz couldn’t hit left handers until he could; Hanley Ramirez could mash until injury became his kryptonite; Pablo Sandoval was so bad at hitting the ball as a right handed hitter, he gave up trying; Mike Napoli couldn’t swing with that fork stuck in his back; Christian Vazquez was injured before the season even started; Hanigan was injured almost immediately, necessitating the early callup of Blake Swihart. Porcello had the worst season of his career. Buchholz was good and then was injured. Despite all this, The Red Sox were still in the periphery of the race at the All-Star Break, standing only five games under .500. But the Sox went on the road to begin the second half and fell apart. Seven consecutive losses, twelve of fourteen, and the season was once again done. The hits didn’t stop there, as John Farrell was diagnosed with cancer.

The Red Sox are well on their way to a third last place finish in four seasons. However, they also have the best farm system according to MLB.com and ESPN, despite graduating Mookie Betts and Xander Bogaerts over the past two seasons. Rusney Castillo and JBJ have both shown signs that they can hit major league pitching. Henry Owens, Eduardo Rodriguez and Brian Johnson have all made their major league debuts. The bullpen has shuffled through a number of younger options who may be able to help next season.

And the future is bright. Sam Travis could arrive as early as next season. After a slow start, Yoan Moncada is lighting up minor league box scores. Rafael Devers, Manuel Margot, Javier Guerra, Andrew Benintendi, Michael Chavis, Trey Ball, Teddy Stankiewicz, Logan Allen, Anderson Espinoza, Roniel Raudes – all just prospects through the minor league system, but all with the potential to get to the majors. Will they all succeed? Unlikely. But if only a few make it to the majors, they could make this downturn a blip on the radar.

When Ben Cherington bids adieu to the Boston Red Sox at the end of the season, he will be considered by many as a poor general manager, a man who led the Red Sox to a nadir last seen during the Butch Hobson era of the mid-90s. But the truth is that if just a couple of injuries didn’t happen, or a couple of young prospects performed slightly better as they adjusted, or the wind was in a different direction, perhaps the Red Sox don’t look to toss him aside for Dombrowski.

For while the Red Sox and Ben Cherington were “lucky” in 2013 that most of the bets paid off handsomely, the 2014 and 2015 Red Sox have been just as “unlucky” that most of the bets have busted. Dombrowski inherits a situation that is far better than it looks in the standings. A fantastic farm system, a core of young up the middle players, and some veterans who are going to want to come back and show they are not as bad as they have been. The Red Sox have already gone from last to first this decade… with the system Cherington has left for Dombrowski, it would not be a surprise to see it happen again.

Brandon Magee is our resident minor league expert, but has also written about the mishandling of injuries by the Red Sox, interim bench coach Dana LeVangie, Pablo SandovalBROCK HOLT!,undrafted free agents, the home run king Mike Hessman, and the baseball and football player,Brandon Magee.

Follow Brandon on Twitter @cuzittt.

Check out Brandon’s weekly Minor League Report and Lisa Carney’s article about John Farrell.

About Brandon Magee 549 Articles
Brandon has worked the graveyard shift for a decade and, like any good vampire, is averse to the sun. His love of the Red Sox is so deep, he follows eight teams on a daily basis. He lives in Norwich, CT where he often goes to Dodd Stadium to watch minor league baseball with his best friend, his wife Dawn.

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