Where the Last-Place Red Sox Went Wrong

August 20, 2015 Updated: August 20, 2015

The Boston Red Sox and newly fired GM Ben Cherington had a number of misfires over the last four years since previous GM Theo Epstein left for Chicago. But the team’s recent hiring of free agent GM Dave Dombrowski is one they finally got right.

Not that he won’t have his work cut out for him though.

As bad as Boston has been since Epstein skipped town and Cherington was put in charge—three last places in four years with a World Series title mixed in—it’s wasn’t due to lack of financial resources or talent. They just made some poor decisions. Let’s recount them.

1. Hiring Bobby Valentine to replace Terry Francona

Valentine hadn’t managed in the majors in nearly 10 years when Boston’s brain trust decided he was the one to take over for the popular—and very successful—Francona. But clearly there must have been good reason that such a smart and experienced guy like Valentine wasn’t wanted in anyone else’s dugout.

Despite a veteran team Valentine couldn’t put the pieces together and the Red Sox suffered through their worst season since 1965 with a 69–93 record. Valentine was released as soon as the year was over and hasn’t been heard from since.

2. Giving Pablo Sandoval and Hanley Ramírez Outlandish Contracts

Understand this: bringing in a costly free agent is always a risk. But it’s even more risky when that player/athlete is already battling weight issues.

The 5-foot-11, 255-pound Sandoval never looked like he was in great shape, but he got the job done—at the plate anyway—with a .294 career average as a Giant and a pair of All-Star selections.

With an opening at third base the Red Sox swooped in and gave the 28-year-old an outlandish five-year, $95 million deal that has not paid dividends in the least.

Sandoval is currently struggling at the plate with a .258 batting average and with his fielding numbers looking just as bad as his hitting numbers, the contract has quickly turned into an albatross—even worse than Ramírez’s.

The 31-year-old Ramírez, who has been rumored to be a less-than-great-teammate in previous stops with the Marlins and Dodgers, signed on for $88 million over four years. As if signing someone with character red flags past their 30th birthday for an obscene amount of money wasn’t enough, the Red Sox decided to add one more barrier to his success and have him play a new position—left field.

The experiment has failed terribly as the numbers suggest. Ramírez—who has previously only been an infielder in the majors—is one of the worst outfielders in the game. Meanwhile his hitting—which was the main reason they signed him—hasn’t come around. The former batting champion and MVP runner-up is hitting just .259, though he does have a somewhat-redeeming 19 home runs thus far. The whole package though is not worth $22 million a year.

3. Not Signing Jon Lester: Extending Rick Porcello

As if overpaying for both Ramírez and Sandoval wasn’t enough, the Red Sox were then out-bid in their attempt to sign Jon Lester—their former ace starter who was dealt at the 2014 trade deadline, and arguably the one player they needed the most. Instead the Epstein-led Cubs swooped in and signed him for $155 million over six years.

Without an ace on their roster, Boston accumulated a bunch of middle-of-the-rotation starters including Rick Porcello, who they got from Detroit (when Dombrowski was their GM) for slugger Yoenis Cespedes. The Red Sox then signed Porcello, who had an unimpressive career ERA of 4.30 heading into 2015, to a jaw-dropping four-year, $82.5 million extension (that starts in 2016) during the first week of the season. He’s responded with a year to forget: a 5–11 record with an ERA of 5.81.

Meanwhile Lester has a 8–9 record with a 3.58 ERA for the wild card-leading Cubs.