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Moves That Boston Red Sox GM Ben Cherington Wishes He Could Take Back

Jonathan IrwinContributor IINovember 17, 2016

Moves That Boston Red Sox GM Ben Cherington Wishes He Could Take Back

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    After a disappointing 2011, there was hope that GM Ben Cherington would find a way to fix the Boston Red Sox ship.

    While there were plenty of factors working against Cherington's success, the fact remains that the Sox were inevitably in for another disappointing season in 2012.

    There's plenty of hope for Boston's future, and Cherginton's as good a GM as any to be leading the way. But this is a live-and-learn kind of job, and Cherington's had his fair share of learning experiences.

    Here's a look at some of the GM's most regrettable moves after his first season as Sox GM.

Trading Jed Lowrie

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    It only seems fitting that on the night of Jed Lowrie being traded to the Athletics, we look back at the first time the shortstop was shipped from one team to another.

    There was an obvious need to upgrade Boston's bullpen heading into the 2012 season. It's the reason that Andrew Bailey was acquired—more on him later—and the reason Lowrie was traded.

    In December, 2012, the now 29-year-old was traded from Boston (along with Kyle Weiland) for Astros reliever Mark Melancon.

    Melancon was coming off a career year, posting a 2.54 K/BB and 2.78 ERA in 71 appearances. Lowrie was always a player with plenty of upside, but constant injuries had held him back.

    While injuries were still an issue for Lowrie (he only played in 97 games last season), he provided great offensive punch at one of the league's thinnest positions.

    Lowrie had 16 home runs last season on his way to posting a solid .769 OPS.

    Melancon, on the other hand, was a complete failure, splitting time between Boston and Triple-A Pawtucket. The right-hander finished his year with a 6.20 ERA and a career-worst 9.0 H/9.

    One year later, and Cherington has since packaged Melancon to the Pirates in the Joel Hanrahan deal. And Boston is still in need of a shortstop.

Acquiring Andrew Bailey

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    When Boston acquired Andrew Bailey, it seemed like a great move.

    The Red Sox found a shutdown closer to replace Jonathan Papelbon. All they really lost was a fringe prospect (Miles Head) and an outfielder who constantly failed to reach his potential (Josh Reddick).

    For all his upside, Bailey deserved some caution. Injuries had been an issue in his career, and he had just 87 appearances over his previous two seasons.

    Those injuries became the real crux of this trade, as Bailey made just 19 appearances for Boston in 2012, pitching to the tune of a 7.04 ERA and 1.891 WHIP.

    Oakland, meanwhile, found fantastic return from both players.

    Miles Head took steps forward in the power department, emerging as a top prospect in an already deep A's farm system.

    Reddick enjoyed a tremendous breakout campaign with Oakland, notching career highs in home runs (32), RBI (85) and stolen bases (11).

    He also played stellar defense, registering an 18.5 UZR while spending time in both right and center.

    Even if Reddick sees some regression next season (he had a .305 OBP and 115 strikeouts), Oakland still comes out on top of this move.

    One offseason later and Ben Cherington has already been forced to trade for a new closer—this time Pittsburgh's Joel Hanrahan—making this trade a monumental bust.

Converting Daniel Bard to a Starter

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    This is a move that Cherington can't take all the blame for. It was a decision made by several levels of the organization, but still one the GM deserves some blame for.

    With a desperate need for starting pitching heading into 2012, Boston made the eventual decision to move reliever Daniel Bard to the rotation.

    There were plenty of warning signs against such a move.

    Bard had struggled in the minors as a starter, which is why he was converted to a reliever. He also lacked a solid third pitch to round out his repertoire.

    But the signs were ignored, and the conversion went about as good as expected.

    Bard made just 10 starts for Boston last season, going 5-6 with a 6.22 ERA and nauseating 1.736 WHIP. Command was no doubt an issue, with Bard walking more batters per nine than he struck out.

    Heading into 2013, there are questions of whether Bard will ever be able to retain his effectiveness—even if converted back to a reliever.

    Even though Cherington wasn't 100 percent the mastermind behind this move, it's surely a decision he'd like to take a mulligan on.

Trading Michael Bowden for Marlon Byrd

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    It wasn't bad enough that the Red Sox got virtually nothing in return for former GM Theo Epstein. They had to follow that up by throwing even more talent Chicago's way, once again for minimal return.

    Looking for outfield depth partway into the 2012 season, Cherington made the decision to acquire Marlon Byrd from the Cubs. In return Chicago got right-hander Michael Bowden and a player to be named later.

    Byrd—who had struggled with injuries the year before—had an Earth-shattering .070 batting average in 13 games with the Cubs at the time of the trade.

    In 34 games with Boston, he would go on to post a .606 OPS. The team had released him by June.

    Bowden, who was once a top pitching prospect for Boston, was entering the season a converted reliever looking toward his first MLB season in the bullpen.

    Never given a full chance in Boston's 'pen, Bowden had a breakout year for the Cubs. He finished his 2012 with a 2.95 ERA in 30 appearances for Chicago.

    It's far from the worst deal Cherington ever made, but one in which Boston gave up value for virtually nothing. And if Bowden continues to shine as a reliever, this will just get more and more regrettable.

Not Making the Blockbuster Deal Sooner

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    There's a double-sided coin with this move.

    On one hand, there's the fact that Ben Cherington pulled off the improbable, trading Josh Beckett, Adrian Gonzalez and Carl Crawford all in one move.

    In return he nabbed two solid pitching prospects in Rubby De La Rosa and Allen Webster.

    On the other side of the coin is the fact that Cherington pulled the trigger on the trade in August, well after the July trade deadline.

    Forced to work a deal through the waiver wire, Cherington's options were limited when it came to finding a trade partner.

    If he had made such a deal in July, he could have had a lot more freedom in making a trade.

    While the GM deserves major kudos for pulling off such a fantastic blockbuster, it's hard not to wonder if he could have gotten more a month earlier.

Not Bringing Back Cody Ross for 2013

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    This move has yet to play out, but it's still one that deserves a long look.

    Cody Ross was fantastic for Boston last season. He led the team in RBI (81), missed out on the team home run lead by three (22) and posted a near career-best .807 OPS.

    Despite questionable defense heading into the season, Ross posted a solid UZR of 3.5 in right field.

    It was expected that Boston would make retaining the fielder a priority this offseason, but instead took a different route.

    Often citing "asking price" as being an issue, Ben Cherington signed free agent Shane Victorino this winter instead of Ross.

    Not only was Ross the younger (by 23 days) and more power-savvy of the two options, he just happened to come cheaper—signing for three years and $26 million, over Victorino's three years and $39 million.

    The only way the Victorino signing makes sense is if Boston wants a backup center fielder in case Jacoby Ellsbury is inevitably traded.

    But even then, top prospect Jackie Bradley Jr. is right around the corner from taking over center field.

    Victorino is a good player, and he has his merits. But with Bradley Jr. on his way, and Ross coming out the cheaper option, not re-signing the veteran outfielder just didn't make sense.

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