The Boston Red Sox did a disservice to their fan base this off-season as they strung them along and stayed on the back-page of the papers by making just enough of a bid to stay in the Jon Lester negotiations–without any intention of actually signing him. The Red Sox front office had painted themselves into a corner with some bad public relations work to where they had to make what looked like an actual attempt, but in reality they had two previous opportunities to keep Lester and passed on both occasions:
First, in spring training they failed to make a reasonable offer and insulted Lester and his agent with an extreme low-ball offer of four-years for $70 million when he was clearly looking for a long-term contract in the ballpark of that which Detroit’s Max Scherzer had turned down. If the Red Sox had wanted Lester as a top priority, the team would have avoided the insulting offer and he would have been signed well before opening day.
Second, if they wanted to give him a real offer once free agency opened the front office would never had traded Lester to Oakland over the summer before the trading deadline. If the Red Sox had kept him, they would have had an exclusive window to negotiate and sign him before free agency began. The team passed on that opportunity as well by unloading him to Oakland for a player they had no intention of keeping. Yoenis Cespedes never fit the Red Sox philosophy at the plate and was always intended to be a chip to be traded.
After the 2014 season, the Red Sox only made enough of an offer to look interested without doing what it would take to bring Jon Lester back to Boston.
Really, Lester should be upset at himself for allowing himself to be used by the Red Sox front office. The Red Sox basically slapped Lester across the face with a low-market offer in the spring. The Red Sox then traded him. Lester–in a point missed by many of the fans upset at him for not signing a below-market deal in Boston –has every right to go out in a free market after playing for years at a below market level. As a top-of-the-rotation left-handed pitcher in his prime he is crazy to make as much money as he can for himself and his family. He pitched many years at a price-tag below his value to get to free agency. He does not owe the city of Boston, the Red Sox organization, and the fans anything.
So the Red Sox front office was able to let out a collective breath that Lester did not take the deal that they offered him which they never intended for him to take and was just offered to him as a public relations move to appease the fanbase, then immediately got down to doing exactly what they planned on all along: Rebuild the pitching staff with talented young hurlers who have upside. They did it, and they gave up NOTHING to get three quality starters.
With chips leftover from their house-cleaning when they dumped over $200 million in bad contracts on the Dodgers, they sent the two future middle relievers they got from Los Angeles to the Arizona Diamondbacks. In exchange for ground-ball tossing/ best pickoff move in baseball/big upside lefty Wade Miley the Red Sox gave away Triple-A starting pitchers Rubby De La Rosa and Allen Webster.
Miley is a good fit for Boston with his ground ball and strike-out rates, and he could blossom into a top-line starter. De La Rosa and Webster came over from Los Angeles as part of the package to take on the contracts of Adrian Gonzalez, Carl Crawford, and Josh Beckett. While both have potential, neither are young, top-line prospects. If they stick in the major leagues, they are not frontline starters. At best, they could contribute in a weak bullpen or be a fringe starter on a bad team.
The Red Sox then swung a deal with the Detroit Tigers for young starter Rick Porcello who is still only 26 years old and still has upside. Porcello pitched over 200 innings, won 15 games, and had an ERA under 3.50. All the Red Sox gave up was Cespedes, another future middle reliever/fringe fifth starter Alex Wilson, and a 19-year old prospect who has already had Tommy John surgery and has not pitched a game above rookie league (sub single-A) yet. Cespedes was acquired to be traded and Porcello is a potential number two or three starter for the Red Sox.
Finally, the Red Sox got “the one who got away” back by signing former farmhand Justin Masterson back after he blossomed in Cleveland. Yes, Masterson was injured last year and cost himself some money, but for less than $10 million guaranteed on a one-year incentive-laden deal, the Red Sox got a pitcher they know well and who was the number one starter for a team that made the playoffs back in 2013. Masterson is another ground-ball machine who should enjoy the long infield grass and Gold Glove second baseman (and underrated Pablo Sandoval at third base) of Fenway Park like Miley will as well.
Somehow, the Red Sox are one big starting pitcher (James Shields? Trade for Cole Hamels? Trade for Jordan Zimmerman or Doug Fister?) from finishing a complete rotation rebuild and finishing the off-season with their usual strong depth and affordable pieces not breaking the bank or limiting their roster flexibility. With Sandoval and Hanley Ramirez providing additional pop and production and a potential return to health for second baseman Dustin Pedroia, the lineup should be back to its usual on-base percentage and slugging ways.
Finally, they did not sacrifice a single top prospect while adding three starting pitchers for the price of Jon Lester. Consider the list of remaining prospects the Red Sox have retained to contribute in 2015 or supplement the roster in the next few seasons: catchers Christian Vazquez and Blake Swihart, shortstops Xander Bogaerts and Deven Marrero, second baseman/outfielder Mookie Betts, outfielders Manuel Margot and Rusney Castillo (is the 27-year old CUban considered a “prospect”?), starting pitchers Brandon Workman, Henry Owens, Matt Barnes, Anthony Ranaudo, Edwin Escobar and Eduardo Rodriguez.
The Sox still have their extremely deep farm system, they did not overpay for any starting pitchers over 30 (at least not yet!), and have a deep rotation of experienced young arms in Justin Masterson, Wade Miley, Rick Porcello, and Joe Kelly and added punch in the lineup.
Jon Lester was clearly never coming back to Boston, but the non-public relations work done so far by the front office is a good start for the Red Sox in this pivotal off-season.