By: Sam Rowley
With Cherington out in Boston, Sam felt it a good time to review his biggest mistakes in Boston.
The Ben Cherington era in Boston officially came to an end on Tuesday when the Red Sox replaced Cherington with Dave Dombrowski as president of baseball operations. Seeing his tenure has ended, let’s take a look at the biggest mistakes of the man who brought Boston a World Series in 2013 but also delivered three last place finishes.
Trading Jose Iglesias in 2013
On July 30, 2013, the Red Sox traded Jose Iglesias away in a three-team deal involving the Detroit Tigers and the Chicago White Sox that brought right-hander Jake Peavy to Boston. Cherington, frustrated with Iglesias’s inability to hit against quality major league pitching, figured he could get an established pitcher for their playoff push in exchange for the wiz shortstop. While some may look back on this as a good trade, seeing Boston ended up winning the 2013 world series, the addition of Peavy really did nothing to help the Sox. The Red Sox lost Game 4 of the 2013 ALCS and Game 3 of the 2013 world series, both games in which Peavy started. In his time with the Red Sox, Peavy went 5-11, certainly not worth giving up a player of the caliber of Jose Iglesias. Meanwhile Iglesias is currently hitting .309 in Detroit. Imagine a Boston infield with Jose Iglesias, Xander Bogaerts, Dustin Pedroia/Brock Holt. That would have been something special to watch. It also would have likely prevented the signing of Pablo Sandoval (I’ll get to that later). Almost a year later, the Sox traded Peavy to the Giants for prospects Edwin Escobar and Heath Hembree, both of whom have not reached the majors. Basically, Ben Cherington traded a star shortstop for two nobody pitchers.
Trading Jon Lester in 2014
Hours before the 2014 trade deadline, Cherington dealt one of the most accomplished left-handed pitchers in Red Sox history, Jon Lester, to the Oakland Athletics in exchange for left field slugger Yoenis Cespedes. Ben Cherington justified the move by saying that it would be harder to acquire a right-handed bat in the offseason, and that they would have an easier time rebuilding the starting rotation in the offseason. The Sox also figured that Lester going to the A’s would just be a rental and that they could resign him after the season, seeing his contract expired at the end of the 2014. Well, that didn’t happen as the Cubs snagged him. The Sox missed out on re-signing lester and ended up trading Yoenis Cespedes to Detroit for righthander Rick Porcello. Basically, the Sox traded Jon Lester for Rick Porcello (more on that later).
Trading John Lackey in 2014
This one is tough to swallow. On the same day Ben Cherington got rid of Jon Lester, he got rid of John Lackey as well. He dealt Lackey to St. Louis with minor league pitcher Corey Littrell in exchange for Allen Craig and Joe Kelly. This seemed like a solid deal at the time, dealing an established major league pitcher for a quality bat in Allen Craig and a good, young pitcher in Joe Kelly. Maybe St. Louis knew something that Ben Cherington didn’t. This trade could not have worked out worse for the Red Sox. Joe Kelly has been a disappointment and Allen Craig has vastly underperformed. Craig has spent the majority of this season in Triple A and Kelly has seen time there as well. Meanwhile John Lackey is flourishing in St. Louis, having one of his best years at age 36. Currently he possesses a 2.87 ERA and a 10-7 record. Again, this could not have worked out worse for the Red Sox.
Extending Porcello / Not Signing Lester
Rick Porcello has not lived up to expectations this year, so we’ll cut Ben Cherington a little slack in that regard. However, Cherington prematurely signed Porcello to an $82.5 million dollar extension through 2019 only a week into his time in Boston. Porcello, coming off of an excellent year in Detroit, was set to hit the free agent market at the end of this season, so I see Ben Cherington’s motivation to lock him up for the future. However, Cherington should have at least waited two months to see how Porcello performed in a bigger market with increased pressure. That would have been smart considering Porcello owns a 5-11 record this year with a 5.81 ERA. The fact that the Sox were willing to give an $82.5 million extension to an unproven pitcher when they could have used this money to further compete in the Jon Lester bidding war is a bit confusing. I’m sure looking back on it John Henry wishes he had reached a little deeper into his bottomless pit of money to reacquire Lester.
Signing Yoan Moncada
Some people like this move but I am not a fan of it. I feel that Cherington felt pressured to take action following the major disappointment of last season by making a big splash in the international market. Moncada, a 20 year old second baseman and one of the top prospects in Boston’s farm system, possesses undeniable talent. However, I really feel that Cherington did not have to make this move. The Red Sox farm system ranks number 1 in the majors and is loaded with middle infield prospects. To go out and sign another one for $60 million wastes money and creates playing time log jams throughout all levels of the Red Sox system. If he turns out to be something special and plays in Boston for a long time, I will eat my words. But again, observing the current starting rotation, it would have been nice for that money to be used on someone like Jon Lester.
Signing Pablo Sandoval / Not Trading for Josh Donaldson
The blame for this one falls more on the shoulders of John Henry, Tom Werner, and Larry Lucchino than on Ben Cherington. Cherington really wanted to make a trade with the Oakland A’s for Josh Donaldson, who emerged last season as one of the premier third basemen in major league baseball. Making a trade would have meant giving up top prospects in the Red Sox farm system, but it would have been worth it. Donaldson currently hits .296 with 33 HR and leads the race for the American League MVP award. He also would have come to Boston making the league minimum salary of 500K. Instead, management opted for a different Bay area third baseman, Pablo Sandoval. Sandoval, coming off of his third world series championship in five years, foolishly left San Francisco for Boston. Management, even more foolish, signed him to a four year $88 million contract. So far Sandoval has not won over the Boston fanbase. Thats pretty hard to do when you're making $22 million each year and are only hitting .258 with 10 HR and 39 RBI for a last place team. Thats even harder to do when you leave the dugout during a game to go look at your phone in the bathroom. Sandoval has been looking better lately, but still, the better move would have been to acquire Donaldson.
Signing Hanley Ramirez
This is the worst decision Cherington has made during his time as Sox GM. The Sox are currently paying $22 million each year for Hanley, the worst defensive left fielder in the majors, to hit .254. Hanley also simply does not give a S%$# about anything. The way he carries himself and his body language suggest that he would rather be sleeping. Seeing he's playing so poorly and has such a big contract, they can’t trade him. Who wants that kind of production for that much money? This move will forever be a head scratcher.