Red Sox Still Haunted by Ben Cherington's Horrible Legacy

Ben Cherington wasn’t fired by the Red Sox; he resigned. No matter, there are good reasons that he is no longer the team's General Manager.

The Red Sox won 71 games in 2014 and 78 games in 2015, finishing in last place both seasons.

The poor performance of the team aside, Cherington made a series of terrible personnel decisions that are still hampering the Red Sox.

At this point, it is well established that Cherington wildly overpaid for the underperforming Pablo Sandoval and Hanley Ramirez.

Cherington gave Sandoval — an obese third baseman, whose OPS had declined for three consecutive years before coming to Boston — a five year, $95 million contract with a sixth-year option that requires a $5 million buyout. This means Sandoval is guaranteed $100 by the Red Sox.

Sandoval responded by posting the following numbers last season: .245/.292/.366/.658, with 10 home runs and 47 RBI over 126 games.

If Sandoval had been playing for the league minimum, those numbers would have been unacceptable, and likely would have cost him his job at some point in the season.

However, considering the size of his contract, those numbers were disgraceful. Then there were the 15 errors, poor range and generally weak defense, as well.

Cherington gave Ramirez — a career shortstop — a four-year, $88 million contract to play left field. The pact has a fifth-year vesting option worth $22 million, which almost certainly will vest. If so, that brings the total value of the deal to $110 million.

Ramirez responded by tying a club record with 10 homers in April, but hit just nine more over the next five months. Ramirez ultimately posted a slash line of .249/.291/.426/.717, with just 53 RBI, over 105 games. He failed miserably in the field and at the plate, and became a lightning rod for criticism (deservedly so).

Ramirez is now the team’s first baseman, and if spring training is any indication of what’s to come, he can handle the position better than left field. Being back in the infield appears to be good for him. Handling the ball on virtually every play has reengaged him, and playing first base has more similarities to his natural position than left field ever would.

But those were just the most obvious of Cherington’s terrible decisions.

The former Boston GM gave righty Rick Porcello a four-year, $82.5 million deal that only kicks in this season. Cherington did this despite the fact that Porcello had reached 200 innings just once in six seasons, while posting a 4.33 career ERA to that point.

Given those numbers, does that seem like a reasonable contract offer to you? (It’s a rhetorical question.)

Porcello responded by having the worst season of his rather unremarkable career, going 9-15 with a 4.92 ERA and a 1.36 WHIP over just 172 innings. In short, he was a disaster.

Yet, there were even more bad decisions by Cherington.

The Red Sox GM gave Justin Masterson a 1-year, $9.5 million deal prior to the 2015 season, despite his 2014 struggles with the Indians and Cardinals.

The righty was so ineffective in 2015 that the Sox designated him ‪for assignment on August 9. Masterson compiled a 5.61 ERA, with a 1.60 WHIP and a 49/27 K/BB ratio over 59 1/3 innings — split between nine starts and nine relief appearances.

Though his was just a 1-year deal, Masterson was clearly overpaid -- given that he had gone 7-9 with a 5.88 ERA and a 1.63 WHIP in 2014. To say that the pitcher was overpaid, and underperformed, would be an understatement.

But Sandoval, Ramirez, Porcello and Masterson were merely Cherington’s bad decisions last offseason.

If you go back a year earlier, there were two other horrendous decisions that still haunt the Red Sox today, and that will continue to do so for the next few years.

Cherington signed Rusney Castillo, a Cuban player about whom little was known, to a 7-year, $72.5 million contract. In reality, it was a six-year $72.4 million deal since Castillo signed his deal in late August 2014 and played in just 10 games that season, while being paid $100,000.

Castillo played in just 80 games last season, posting a slash line of .253/.288/.359/.647, with 5 homers, 10 doubles, and 29 RBI. For that, he was paid $10.5 million.

But that’s not the worst of it.

Castillo does not appear to a major league-quality player, and he lost the starting left fielder job to utility infielder Brock Holt, who has a career slugging percentage of .370, with just six homers in 1,027 big league at-bats.

That’s not the profile of a left fielder, yet he still beat Castillo for the position.

That’s an embarrassment for Castillo, but it’s also an embarrassment (and a nightmare) for the Red Sox, who still owe him $56.5 million dollars over the next five seasons. Castillo is a player who could ultimately end up as the richest player in minor league baseball.

But he’ll have competition.

Allen Craig will be paid $9 million by the Red Sox this season to play in Pawtucket. That’s not all; the Sox also owe Craig an additional $11 million for the 2017 season. And here’s the kicker: Craig isn’t even on the 40-man roster anymore. In other words, if the Sox want to call him up to the big league club at any point, they must first cut or trade another player. Stunning!

Cherington obtained Craig and righty Joe Kelly (who was so bad last year that he was demoted to the minors) from St. Louis in exchange for John Lackey. Cherington got fleeced. Lackey won 13 games and threw 218 innings for the Cardinals last season, while posting a terrific 2.77 ERA.

To review, Cherington saddled the Red Sox with expensive long term contracts for Hanley Ramirez, Pablo Sandoval, Rick Porcello and Rusney Castillo, who cumulatively cost a whopping $365 million.

Include Allen Craig, who will cost the Red Sox a total of $31.25 (including a $1 million buyout after the 2017 season), and Justin Masterson’s $9.5 contract from last year, and it adds another $40.75 million to Cherington’s highly expensive, bad decisions.

These horrible choices cannot be glossed over. They will haunt the Red Sox for years to come.

Yes, Boston is a big market club, and ownership has deep pockets. But these deals have consequences in that they prevent money from being allocated elsewhere for other needs.

But they will also create redundancies, in that the Sox will have to pay other players to assume the roles of, or pick up the slack for, these failed players (yes, Brock Holt and Travis Shaw are cheap, but they may not be long term answers).

Let’s not forget that Sandoval and Castillo will each be paid tens of millions to warm the bench this year (to start the season, at least), while Craig will be paid millions more to play in Pawtucket. Meanwhile, Porcello will be paid a hefty $20 million to be the fourth starter this year.

It’s tough to overstate how bad Cherington’s personnel decisions were, and how much he has hampered this club going forward. It's fitting that he can no longer exercise such poor judgement.

The only thing more fitting would have been if ownership had truly held him accountable, and fired him.

The 2013 World Series was as wonderful as it was unexpected, but the Sox finished in last place in three of Cherington’s four years as general manager.

It’s appropriate that he’s now gone. But, boy, did he leave an epic mess in his wake.