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MLB: Time To Reassess Red Sox GM Ben Cherington And His Past Deals

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With the MLB trade deadline in the books and the Boston Red Sox reeling, now is a good time to take a look at how well Boston general manager Ben Cherington has done with his midseason deals.

Cherington has been GM since 2011 but has been a part of the Red Sox decision-making since 1999. So while the body of evidence is small, there are some tell-tale signs for what he’ll try to do in the next few days.

The Red Sox are mired in last place in the AL East and came out of the All-Star break being swept by both the Angels and Astros. That puts Boston clearly in a sell mode. With veterans who could make a difference to a contending team, they have some chips, though most are likely to get a marginal return.

Their four years under Cherington have been one up and a lot of downs. They finished last in 2012 and 2014, and look to be headed that way again. The now seemingly anomalous 2013 World Series triumph appears to be a major outlier.

So what has Cherington done in the past three deadline frenzys? Let’s take a closer look.


June/July: 3B Kevin Youkilis to White Sox for CF Brent Lillibridge and RHP Zach Stewart (June 25).  Lillibridge to Indians for RHP Jose De La Torre (July 24). RHP Matt Albers and OF Scott Podsednick to Diamondbacks for LHP Craig Breslow (July 31). 1B Lars Anderson to Indians for RHP Stephen Wright (July 31).

August: Garrett Mock to Astros for future considerations (August 3). OF Jeremias Pineda to Astros for 3B Danny Valencia (August 4). C Kelly Shoppach to Mets for player to be named later (August 14). 1b Adrian Gonzalez, OF Carl Crawford, RHP Josh Beckett, and SS Nick Punto to Dodgers for 1B James Loney, 2B Ivan DeJesus, RHP Allen Webster and two players to be named later (August 25).

A rather ho-hum series of transactions until you get to the end. Giving away fan favorite Youkilis broke some hearts of Fenway faithful, but at the time, he was injury-prone and hitting .233. And then-prospect Will Middlebrooks was hitting .326 and waiting for his chance. Breslow has been a consistent bullpen arm ever since and Wright has been up and down with the Sox all season.

That waiver-period trade of three expensive (and some rumors indicated clubhouse-unfriendly) players and Punto to the Dodgers shocked Red Sox nation. The move was all about salary relief, as the Sox extricated themselves from $250 million in contracts.

The Red Sox limped along the rest of the season but Cherington got strong marks for the blockbuster deal, in the process acquiring some potential arms to bolster the farm system.


June/July:  SS Pedro Ciriaco to Padres for future considerations (June 14). LF Brandon Jacobs to White Sox for LHP Matt Thornton (July 13). SS Jose Iglesias, RHP Francellis Montas, SS Cleuluis Rondon, and RHP Jeffrey Wendelken to White Sox and Tigers for RHP Jake Peavy and RHP Villareal (July 31).

August: RHP Clayton Mortensen to Royals for OF Quintin Berry (August 27). RHP Nefi Ogando to Phillies for SS John McDonald.

With money saved from the Punto Trade (as one Boston blog refers to it), the Sox signed Ryan Dempster, Jonny Gomes, Mike Napoli, Koji Uehara, and Shane Victorino, four key pieces to their championship run. But it was the acquisition of Peavy that helped solidify the stretch-run rotation. Peavy went 4-1 in 10 starts. While Thornton contributed in the bullpen, he was left off the playoff roster. Berry, a speedster, hit .625 with three stolen bases in limited action. While the Sox gave up a future All-Star in Iglesias, they raised their third World Series trophy in 10 years.


July: LHP Rich Hill to Angels for cash (July 1). Cash to Royals for LHP Ryan Verdugo (July 16). RHP Jake Peavy and cash to Giants for LHP Edwin Escobar and RHP Heath Hembree (July 26). LHP Felix Doubront to Cubs for a player to be named later (July 27). LHP Andrew Miller to Orioles for LHP Eduardo Rodriguez (July 31). LHP Jon Lester, OF Jonny Gomes and cash to A’s for OF Yoenis Cespedes (July 31). RHP John Lackey, LHP Corey Littrell and cash to Cardinals for 1B Allen Craig and RHP Joe Kelly (July 31). SS Stephen Drew to Yankees for 3B Kelly Johnson (July 31).

August: 3B Kelly Johnson and3B Michael Almanzar to Orioles for 2B Jemile Weeks and 2B Ivan DeJesus.

Much like 2012 … and 2015 … the Red Sox were going nowhere fast. So in five days, Cherington traded 4/5s of his starting rotation (Doubront, Lester, Lackey, and Peavy), a top bullpen arm (Miller) and capped off their July by making a trade with the arch-rival Yankees. The Yankees! It was the first trade with New York in 17 years.

The party line was the trades were about the future and giving opportunities to some young prospects. Mookie Betts, Xander Bogaerts, Jackie Bradley Jr., and Middlebrooks got time, as did hurlers Matt Barnes, Hembree, Kelly, Rubby De La Rosa (a PTBNL in the Punto Trade), Anthony Ranaudo, and Webster. All was gearing up for what was supposed to be a monster 2015.


Today, the 2014 trades appear to be disastrous. De La Rosa and Webster play for other teams. Escobar and Hembree are in the minors. Kelly and Craig, the big pieces in the Lackey trade, have also spent time in Pawtucket. Cespedes was traded in the offseason. The lone bright spot: Rodrigues has some flashes of dominance.

But what would the maligned Boston pitching staff look like with Lackey (9-5, 2.88 ERA), Lester (122 strikeouts), and Miller (1.57 ERA, 23 saves) in the mix?

So what did Cherington do? If history is any indication, the easiest predictor is he’ll be busy. His past indicates he’s unafraid to roll the dice and shake up rosters.

And that he did in shipping Victorino to the Angels for utility infielder Josh Rutledge and reliver Ryan Cook from the Oakland A’s

If he wants to start the 2016 retooling, he could also go big. The Sox are still mentioned in Cole Hamels rumors, have reportedly sniffed at Cleveland’s pitching, and pondered making runs at the since-traded Johnny Cueto and Scott Kazmir. and the Sox farm system is stacked.

For Red Sox fans, if nothing else, it was an anti-climatic week to say the least.

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