Should Ben Cherington’s job be safe? A look at his significant deals

–The Boston Globe/Jim Davis


Many missed deadlines ago, back in the mid-’90s when I had just joined the Concord Monitor in New Hampshire as an undrafted free-agent out of the University of Maine, I came down to The Boston Globe for a seminar one day.

I couldn’t tell you the specific topic if you paid me — hell, it may have been “The Eternal Life of the Print Product’’ for all I recall — but I do remember something Don Skwar, then the Globe sports editor and a featured speaker that day, said.

“A columnist should never,’’ he said gravely, “take his topic from something being discussed on sports radio.’’


It’s stayed with me through the years, perhaps in part because it felt like a you’ll-never-get-hired-here admonishment to an unsure young sports writer, but also because in my several weeks’ worth of journalistic wisdom at the time, I disagreed with it but didn’t have the nerve to say so.

He asked for a show of hands, asking if anyone has done this. I do not recall a single sportswriter limb shooting northward, and that includes those belonging to one of the other panelists — Michael Holley, then a Globe columnist, now of course, a sports-radio host. I think that’s what they call irony.

I think of this now only because the topic of this column actually is not My Boring Adventures in ‘90s Journalistic Seminars — that’s for later in the week — but something I heard being discussed on WEEI’s Dennis and Callahan program the other day: Red Sox general manager Ben Cherington’s track record with transactions since he took the job in October 2011.

It’s a worthwhile discussion, given that the Red Sox have two last-place finishes, a lousy start this year, and a World Series championship on his watch. It’s also one that requires more nuance and detail than can be squeezed into a segment in which at least one of the hosts’ knowledge of the names involved roughly equates to David Ortiz’s batting average this year.


So let’s ignore everything learned from that long-ago seminar and take a look at the significant moves Ben Cherington has made in his three-plus seasons as the Red Sox’ general manager. John Henry says his job is safe. This might offer some clarity on whether it should be.

December 14, 2011

The move: Traded INF/DL Jed Lowrie and P Kyle Weiland to the Houston Astros for P Mark Melancon.

Comment: Melancon was the relief-pitcher version of Joe Kelly. Hey, but they did sign Nick Punto of the future famed “Punto Trade’’ the same day, so there’s that.

Grade: D. Lowrie is a decent player the 62 games per year he isn’t in traction.

December 28, 2011

The deal: Traded minor leaguers Raul Alcantara and, Miles Head and OF Josh Reddick to the Oakland Athletics. Received P Andrew Bailey and OF Ryan Sweeney.

Comment: In retrospect, this one looks rough. Bailey got hurt and Sweeney was roster fodder. Reddick is productive when healthy — he hit 32 homers in ‘12 and won a Gold Glove award, and has submitted a .302/.379/.503 so far this season. But the logic for the deal — that Reddick and Ryan Kalish were redundant — wasn’t faulty. It just didn’t work out. This is not the only Cherington deal we can say this about.

Grade: D

January 21, 2012

The deal: Traded INF Marco Scutaro to the Colorado Rockies for P Clayton Mortensen.

Comment: Scutaro was traded to the Giants during the season and promptly turned into vintage Nomar, hitting .362/.385/.473 in 62 games for the eventual World Series champs. Man, the Giants have a knack for finding the right veteran fits, don’t they?


Grade: Eh, who cares. It was just Scutaro. C, I guess.

January 26, 2012

The deal: Signed OF Cody Ross as a free agent.

Comment: Even though he acted like the love child of the hosts of Intentional Talk, Ross had a nice season for the hapless ‘12 Sox, hitting 22 homers with an .807 OPS.

Grade: B. Actually, make that a B+, with a half-grade boost for having the sense to resist signing him long-term.

April 21, 2012

The deal: Traded P Michael Bowden and Hunter Cervenka to the Cubs for OF Marlon Byrd.

Comment: Byrd looked finished with the Sox, hitting 1 homer (.606 OPS) in 100 at-bats before he was released. He was suspended for PEDs while he was unemployed, but has hit 59 homers in the past two-plus seasons.

Grade: C.

May 2, 2012

The deal: Signed P Mark Prior.

Comment: Worth a flier, even if the glory days (and his speedball) had passed him by. Can you believe he’s nearly six years younger than Koji Uehara?

Grade: No grade. Just sadness.

June 24, 2012

The deal: Traded INF Kevin Youkilis and cash to the Chicago White Sox. Received Brent Lillibridge and Zach Stewart.

Comment: Bobby Valentine was right. Youk was cooked, and they got nothing in return. Actually, less than nothing. Lillibridge was worth minus-0.3 bWAR with the Red Sox, while Stewart was even worse at minus-0.6.

Grade: D.

July 31, 2012

The deal: Traded P Matt Albers and OF Scott Podsednik to the Arizona Diamondbacks for P Craig Breslow.

Comment: It’s not a leap of hyperbole to suggest that the Red Sox would not have won the 2013 World Series without Breslow’s contributions.

Grade: B+. It would be an A except for the fact that he’s been brutal for a year-plus now.

August 25, 2012

The deal: Traded P Josh Beckett, OF Carl Crawford, 1B Adrian Gonzalez, INF Nick Punto and cash to the Los Angeles Dodgers for 1B James Loney, SS Ivan DeJesus, OF Jerry Sands, and Ps Allen Webster and Ruby De La Rosa.

Comment: The Dodgers could offer Joc Pederson straight-up for Joe Kelly and it still would be the second-most magnanimous gift they ever gave to the Red Sox. I hope Cherington sends Stan Kasten a thank-you note and gift much more thoughtful than an edible arrangement on the deal’s anniversary every year.

Grade: A+, though it must be noted that Gonzalez has been everything the Dodgers hoped, and he was the reason they took on the other two dopes.

October 21, 2012

The deal: Traded SS Mike Aviles to the Blue Jays for P David Carpenter and manager John Farrell.

Comment: I’ll leave it to you to suggest that maybe they kept the wrong guy in that trade, but Carpenter did have a 1.78 ERA for the Braves in ‘13. (He’s been mediocre for the Yankees this year, though.)

Grade: B. Sarcasm aside, Farrell did win a World Series his first year here, and despite Shaughnessy’s protestations, it does indeed count.

Dec. 1-26, 2012

The deals: Signed OF Jonny Gomes and Shane Victorino, RP Koji Uehara, SP Ryan Dempster, and SS Stephen Drew.

Comment: This has to be the best three-week stretch of Cherington’s career — other than anything and everything that occurred in October 2012, that is, and that was in part made possible by this. Cherington sensibly redistributed some of the savings gained from the Dodgers deal to find a 6.1 WAR corner outfielder, a lefty-mashing, ‘merica-lovin’ platoon outfielder, a closer who delivered a season Mariano Rivera would admire, a durable but slightly-below league-average starter, and a steady defensive shortstop with a .777 OPS (yeah, you’d take that now, Drew haters). It was also in this window that he acquired Brock Holt (and Joel Hanrahan, while unloaded Melancon), and a month later Cherington signed the essential Mike Napoli.

Grade: A+. If Cherington needs to make his case for keeping his job in the near future, he should begin by pointing to December 2012 and saying, “That was me. I did all that.’’

July 30, 2013

The deal: As part of a three-team trade, sent SS Jose Iglesias to the Tigers and minor leaguers Frankie Montas, Cleuluis Rondon, and Jeffrey Wendelken to the Chicago White Sox. Received Brayan Villarreal from the Tigers and P Jake Peavy from the White Sox. The Tigers sent OF Avisail Garcia to the White Sox.

Comment: After missing all of last season with shin-splints, the slick Iglesias is having another one of those how-the-hell-is-he-doing-it? seasons at the plate, batting .338 with an .822 OPS. (Actually, we know how he’s doing it: He has a .366 batting average on balls in play; the man has already received a lifetime of bloops and bleeders in his favor.) But there is no reason to lament the deal. He’s three years older than Xander Bogaerts, who will be a much different hitter at 25. And Peavy played a major role in keeping the Red Sox rolling after Clay Buchholz was injured. No regrets.

Grade: B

December 4-7, 2013

The deals: Signed A.J. Pierzynski, Carlos Rivero, and Edward Mujica as free agents.

Comment: Who knew Carlos Rivero would be the best of that group? Hell, who knew Carlos Rivero?

Grades: F, Who?, F-

January 22, 2014

The deal: Signed Grady Sizemore as a free agent.

Comment: Low-risk, no reward. He was released by the Phillies Tuesday, his once-great skills eroded, the scars remaining.

Grade: C. It was worth a shot.

July 26, 2014

The deal: Traded P Jake Peavy to the Giants for Ps Edwin Escobar and Heath Hembree.

Comment: Duck boats and cable cars make for a heck of a Weird Vehicle Starter Set.

Grade: B.

July 31, 2014

The deals: Traded P John Lackey, minor leaguer Corey Littrell and cash to the Cardinals for OF Allen Craig and P Joe Kelly. Traded Jonny Gomes, Jon Lester and cash to the Athletics for OF Yoenis Cespedes and 2015 competitive balance round B pick. Traded LHP Andrew Miller to the Orioles for LHP Eduardo Rodriguez. Traded SS Stephen Drew to the Yankees for INF Kelly Johnson.

Comment: Call it a disbanding, call it a bloodletting, but a less than a year later, just don’t call it a job well done. The Red Sox got fleeced in the Lackey deal. Lester turned into Rick Porcello, which might look better in a year or two, but looks terrible now. Acquiring Rodriguez was the salvation, but even that deal could have been better — the Red Sox should have paid Miller to return rather than watching their reclamation project join the Yankees. Kelly Johnson was traded… ah, who cares. No one noticed that deal anyway.

Grades: Miller: A. Lackey: D. Lester: C. Drew: I miss that family so.

August 23, 2014

The deal: Signed Rusney Castillo as an amateur free agent.

Comment: They told us he was similar to Ron Gant. No one said it was the Ron Gant who hit .177 for the ‘89 Braves and got sent back to Single-A to learn how to play the outfield.

Grade: C+. Too soon to judge, obviously, but Castillo is awfully unpolished for a player at his prime age. Nice game Tuesday night, though.

November 25, 2014

The deal: Signed OF (cough, cough) Hanley Ramirez as a free agent. Signed 3B Pablo Sandoval as a free agent.

Comment: Well, I still think it’s going to work out, even Sandoval hasn’t moved as much Panda product as Tom Werner might have hoped and Hanley has been the Don Swayze version of Manny so far.

Grades: Hanley: C. Panda: C.

December 11, 2014

The deal: Signed P Justin Masterson as a free agent.

Comment: Had a 7.04 ERA with the Cardinals last year. Please don’t take any more pitchers discarded by the Cardinals.

Grade: D-, with small hope for improvement.

December 11, 2014

The deal: Traded P Alex Wilson and OF Yoenis Cespedes to the Tigers for P Rick Porcello.

Comment: Porcello’s top career statistical comp is Jon Garland. I could have mined the names of every pitcher ever to grip an official Major League Baseball and could not have come up with a better match.

Grade: C. Cespedes was overrated.

December 12, 2014

The deal: Traded Ps Rubby De La Rosa and Allen Webster and minor-leaguer Raymel Flores to the Diamondbacks for Wade Miley.

Comment: Much rather have Rubby.

Grade: C-. And I still don’t know why Miley, who had an 88 ERA+ in the National League last year, was signed to an extension.

December 19, 2014

The deal: Traded 3B Will Middlebrooks to the San Diego Padres for C Ryan Hanigan.

Comment: If you’re pining for Middlebrooks, you’re not paying attention this year, and you weren’t last year, either.

Grade: B-. Hanigan was doing the job before he got hurt.

So on my quick accounting, that’s three As, six Bs, seven Cs, four Ds and two Fs. Not bad, and there would be more As and Bs if we broke out the Uehara-Gomes-Victorino stretch of success into separate transactions. Conclusion? Cherington has hardly been perfect, but he’s had more hits than misses while developing a farm system to envy, remodeling the roster a couple of times, and dealing with a year of Bobby V. His job should not be in jeopardy.

Catching up with old Red Sox friends

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