Red Sox Jon Lester Vs. David Price: A Tale of Two Pitchers

The Boston Red Sox are watching what might have been in Jon Lester playing for the Chicago Cubs, while they contemplate their decision with David Price.

Two different organizational structures but the same ownership group. That’s the difference between what happened to Jon Lester in 2014 and David Price in the 2015 offseason in Boston. The Red Sox still had general manager Ben Cherington when Jon Lester was traded to the Oakland Athletics, not that it was necessarily Mr. Cherington’s fault. The Red Sox then had president of baseball operations Dave Dombrowski to pull the trigger on the deal that saw David Price bring his talents to Boston, and drop yet another playoff game in his career.

Both are seasoned veterans, both have been All-Stars multiple times, and both have been tough lefties in the regular season. Yet, only Lester has the two World Series championships with the Red Sox. Price has no championship rings, but he does have a 2-8 record and a 5.54 ERA in his postseason career.

Lester has five more wins and a 2.63 ERA in his postseason career.

In 2014, there were two times that Lester gave the Red Sox a chance to keep him. One was before he left Boston, the only MLB town that he called home since 2006, in a well-documented meeting outside of Fenway Park with John Henry, the principal owner of the franchise. All cameras pointed to a Lester who seemed very reluctant to leave, grimacing as if the pain of the trade news was worse than any physical blow that he could sustain.

He came back through cancer and sacrificed his blood, sweat, and tears for the team for years, only to be told that he needed to make another sacrifice. He had to leave so that the team could acquire a big hitter named Yoenis Cespedes from the Athletics. Cespedes could rack up home runs and RBIs for the team, who were desperate for some offense to complement designated hitter David Ortiz. Lester was told that the Red Sox would make a strong attempt to reclaim him in the offseason, but that he should enjoy his time on the West coast and try to win another championship while the Athletics were hot going towards the playoffs.

Alas, a championship was not to be in Oakland and neither was Lester to rejoin the Red Sox.

While the Chicago Cubs’ general manager, former Red Sox boss Theo Epstein, made a great offer to Lester, Boston’s brass felt that matching or making a better offer seemed too steep. Lester became a Cub as reluctantly as he left for Oakland, allowing as much time as he could for the Red Sox to make a counter offer against Chicago. It didn’t come, at least not for what Lester and his family eventually agreed upon.

Fast-forward to the 2014 offseason, Cespedes was traded almost immediately for pitcher Rick Porcello, while Pablo Sandoval and Hanley Ramirez signed for big free agent contracts. The team who seemed like family to Lester had just given away the man whom they traded for him for another pitcher, one with an 0-2 record in the postseason.

Porcello, Ramirez, and Sandoval had all disappointed Red Sox Nation greatly in 2015, which put pressure on the team’s front office to find someone to right the ship. When Dombrowski was hired, that spelled the end of Cherington’s time in Boston.

Even so, the Lester trade still lingered on the minds of many Red Sox fans. Their team allowed one of their own to be sent away for outsiders who stunk it up in front of the Fenway faithful, and nothing that was done had changed any of it.

Enter Price.

All of the fanfare, all of the hype that came with Price was the same that Toronto felt in 2015 when they traded for him at the July deadline. The Blue Jays and Red Sox both felt that they had their man to carry them to postseason glory when they obtained his services, promising their fans to get their popcorn ready. The playoff debacle for the Blue Jays was supposedly an enigma, a blip in the otherwise stellar performance of Price in 2015.

At least, that’s what the Red Sox told their fans after signing him to a longer and bigger contract than the one that the Cubs offered Lester.

Bringing us to the present, the Red Sox are out of the 2016 playoffs and the Cubs are three wins away from the World Series. Price only lasted 3.1 innings before getting the hook against the Cleveland Indians in the American League Division Series. Lester made the San Francisco Giants look foolish for eight innings in the National League Division Series, and then he put on a clinic against the Los Angeles Dodgers last night in the NLCS.

Which one deserved the money more?

Next: Red Sox: Buchholz Future In Limbo

Even with Porcello and Ramirez resurrecting their careers in 2016, and Sandoval being replaced by a home-grown prospect in Travis Shaw at third base, the Lester trade sticks in Red Sox Nation like a stab in the back. Did the Red Sox realize their mistake with Lester and try to compensate with Price? Or did the Red Sox just think that Price deserved the money more than Lester? It’s true that Dombrowski and Cherington are not the same men, but the Red Sox still had the same ownership that agreed to both deals within a two-year span. Whomever is to blame, it would be hard to argue with anyone from Red Sox Nation being still upset with what they must feel as a betrayal.

One thing is definite: the fans have never lost their love of Lester, no matter the Price factor.