New Pirates GM Ben Cherington left mixed legacy with Red Sox |

New Pirates GM Ben Cherington left mixed legacy with Red Sox

Ben Cherington signed a few high-profile busts with the Red Sox, including third baseman Pablo Sandoval. In this Nov. 25, 2014, photo, Cherington poses with Sandoval during his introductory news conference in Boston.

How Ben Cherington’s second tenure as a general manager turns out remains to be seen. He will be introduced Monday as the new Pittsburgh Pirates GM.

However, Cherington left a mixed legacy in his first shot at running a baseball operation’s department.

During his four-year stint as Boston’s GM from 2012-15, the Red Sox won the World Series in 2013. They finished last in the American League East in the other three seasons.

He removed more than $250 million from Red Sox’s books with one trade. Yet he eventually added more than $250 million back with three bad free-agent signings.

Cherington’s tenure went to extremes from the time he was hired to replace Theo Epstein on Oct. 25, 2011, to when he refused to accept a No. 2 role and left the organization Aug. 18, 2015, when Dave Dombrowski was hired as president of baseball operations.

The highest of the highs, of course, was winning the World Series. Cherington was named the Major League Baseball Executive of the Year by The Sporting News for that effort.

After a dismal 2012 season that included a blockbuster salary-shedding trade, Cherington attacked the offseason by signing seven mid- and low-level free agents. The group consisted of right-hander Ryan Dempster, reliever Koji Uehara, catcher David Ross, first baseman Mike Napoli, shortstop Stephen Drew and outfielders Jonny Gomes and Shane Victorino.

Cherington also fired Bobby Valentine after one disastrous season as manager and replaced him by trading with the Toronto Blue Jays for John Farrell.

All seven free agents played a role in the Red Sox going 97-65 in the regular season and winning the AL East. Boston then beat the Tampa Bay Rays and Detroit Tigers in the AL playoffs before defeating the St. Louis Cardinals in six games in the World Series.

Farrell finished second in the AL Manager of the Year voting.

Cherington had the money to be aggressive in the free-agent market because of the big trade he made the previous season. The Red Sox shipped Josh Beckett, Adrian Gonzalez, Carl Crawford and Nick Punto to the Los Angeles Dodgers.

Boston got minimal return in the trade but unloaded $258 million in guaranteed salaries. Cherington had inherited the contracts of all four players, who had been acquired by Epstein.

Th trade opened room for the addition of the seven free agents the following winter. Cherington signed those players for a total of $138.95 million, $104.5 million going to Dempster, Napoli and Victorino.

However, it never got better than that for Cherington as he made three ill-fated free agent signings in 2014.

The Red Sox gave seven years and $72.5 million to Cuban outfielder Rusney Castillo during the season. In November, they agreed to a five-year, $95 million deal with free-agent third baseman Pablo Sandoval and signed infielder Hanley Ramirez for four years and $88 million.

Castillo, whose contract does not expire until after next season, made his much-ballyhooed major league debut Sept. 17, 2014, at PNC Park. However, he has been a bust and not played in the big leagues since 2016. In 99 games with the Red Sox, he has batted .262 with seven home runs.

Though still in the organization, the Red Sox long ago dropped Castillo from the 40-man roster so he would not factor in luxury-tax calculations. He is set to make $14.2 million in 2020 to again presumably play at Triple-A Pawtucket.

Sandoval reported to the Red Sox out of shape during spring training in 2015 and never seemed to want to play in Boston. The former San Francisco Giants standout played in 161 games — the equivalent to a full season — during a three-year stint with the Red Sox, hitting .237 with 14 home runs before being released during the 2017 season and returning to the Giants.

Ramirez, a three-time All-Star, batted .260 with 78 homers over four seasons and was released in May 2018.

However, Cherington played an indirect role when the Red Sox won the World Series in ’18. Third baseman Rafael Devers was signed in 2013 as an international amateur free agent from the Dominican Republic, and left fielder Andrew Benintendi was Boston’s first-round draft pick in 2015.

Cherington also acquired left-hander Eduardo Rodriguez from the Baltimore Orioles in a 2014 trade for lefty reliever Andrew Miller, who was two months from free agency.

Cherington was good with the small moves and bad with the big ones.

The thrifty Pirates aren’t the big-spending Red Sox, and they make few big moves. Based on Cherington’s track record, perhaps he will be a better fit in Pittsburgh than Boston.

John Perrotto is a Tribune-Review contributing writer.

Categories: Sports | Pirates
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