The Red Sox Blew It

It’s amazing how quickly a team that has fallen out of favor with its loyal fans can win them over again by winning. What’s even more amazing, however, is how quickly a championship team like the 2013 Boston Red Sox can fade away again. This time a year ago, it looked like the beginning of a new era in Red Sox baseball where they would be contenders year in and year out again, like they were from 2003 to 2009. David Ortiz was the only mainstay from the 2004 team, but Dustin Pedroia and Jon Lester would be the leaders of Boston’s next World Series run. This time a year ago, Jon Lester wanted to stay in Boston. This time a year ago, nobody wanted him to leave. Now, Jon Lester is a member of the Chicago Cubs, and the Red Sox front office has only themselves to blame, if they even wanted him back.

The Red Sox are run by very smart people. I’m convinced of that, even when I don’t like the decisions they make. You can win a World Series by accident, I suppose, but not three in a ten year span. They know what they’re doing, but sometimes it seems like they buy into their own reputations a little too much. They approached Jon Lester’s contract extension negotiations like the Boston Red Sox were the ones who taught him how to throw a baseball and gave him his natural talent. They thought they could put his loyalty to the organization that drafted him to the ultimate test, and that would be enough to keep him in Boston.

In the 2014 spring training, the Red Sox offered Lester the hometown discount to end all hometown discounts: a five year, $70 million deal. Including the club option for a seventh year that the Cubs gave Lester a few days ago, that’s $100 million less than he got on the open market. Lester’s camp was insulted by the offer and did not want to negotiate with the Sox again until after the season.Along the way, Lester had a career year and put himself right up there with Detroit’s Max Scherzer at the top of the list of soon to be free agent pitchers (For the record, I’d rather have Lester than Scherzer. Lester has been a top of the rotation pitcher longer, is left handed, and was not represented by Scott Boras). With the 2014 regular season all but a lost cause by the end of July, the Red Sox traded Lester (along with Jonny Gomes) to the Oakland Athletics for Cuban-born power hitting outfielder and back-to-back Home Run Derby champion Yoenis Cespedes. Any chance of getting hometown preference in the offseason went away for the Res Sox when they traded Lester to Oakland.

What is most frustrating, as a Red Sox fan, about the way the team handled Jon Lester’s future in Boston was that this was absolutely the kind of player worth extending themselves to keep around. He was the the #57 overall pick in the 2002 Major League Baseball Draft, the first draft after John Henry and Tom Werner bought the storied championship-starved baseball club. Before being traded to Oakland, he was the only player in the Red Sox organization who had been with the franchise longer than David Ortiz (who was acquired in 2003). He was a three time All-Star in Boston, who managed to take his game to an even higher level when the games mattered most, despite almost always going up against the other team’s ace. He was the best homegrown pitching talent the Red Sox had developed since some guy named Roger Clemens. He has no history of baseball related injuries that could lead to a decline in his early thirties. The Red Sox took a pitcher who was drafted and developed in Boston, who won two World Series titles in Boston, who beat cancer early in his career in Boston, who would have been an ideal leader and example for Anthony Ranaudo and Henry Owens in Boston, and approached his contract extension like he was some 35 year old reliever with a history of breaking down. It was insulting to Lester, and a slap in the face to Red Sox Nation, who was just starting to feel good about the team again (winning the World Series certainly as that effect) after Fried Chicken and Beer, and the Bobby Valentine season.

I was stunned that the Red Sox were able to acquire Cespedes from Oakland at the trade deadline, and I wrote more than one article in reaction to it (also, before I forget, here is my plea to the Red Sox front office to not trade Lester and to pay him what he’s worth from last summer). Nobody trades their cleanup hitter in the middle of a pennant race, especially when you already have three quality starters like the A’s did (Sonny Gray, Jeff Samardzija, and Scott Kazmir), especially not someone as smart as Brad Pitt’s character from that Aaron Sorkin baseball movie. Billy Beane’s bod plan backfired and the A’s lost the AL West to the Los Angeles Angels of Anaheim (Seriously, when are we going to go back to calling them just the “Anaheim” or “California” Angels again? This is ridiculous!), even though Lester did his job every fifth day, and the Oakland bullpen blew the lead from Lester’s solid Wild Card Game start, inadvertently kicking off the incredible playoff run for the Kansas City Royals that will one day make a much better baseball movie than Moneyball. Cespedes impressed Red Sox fans in his short time in Boston. He hits the ball with real power (something the Red Sox have never been able to develop through their own farm system), and he has a cannon for an arm (something we’ve come to appreciate after years of seeing Johnny Damon and Jacoby Ellsbury struggle to get the ball to the cutoff man at second base from center field), but if anyone was naiive enough to get attached to Cespedes, they were doubly disappointed by the Red Sox this week.

Red Sox fans haven’t been blaming Lester. In fact, many of us were worried that the Sox would try to smear him after he signed with Chicago, and decided to get out in front of it with a Twitter campaign. #SmearCampaign was a rousing success, and if you’re looking for a few laughs from this bummer of a situation, you should check it out (also two of my Tweets made it into this Yahoo Sports article).

The day after Lester signed with the Cubs, the Sox traded Cespedes to Detroit for starting pitcher Rick Porcello. Ultimately, the Red Sox traded Jon Lester for Rick Porcello, even if they were two separate trades a few months apart. The Red Sox also traded pitching prospects Alan Webster and Rubby De La Rosa to the Arizona Diamondbacks for 28 year old left-hander Wade Miley, and signed former Red Sox prospect Justin Masterson (traded to the Cleveland Indians in 2009 for Victor Martinez) to a one year deal after splitting time in 2014 between Cleveland and the St. Louis Cardinals. Right now, the Red Sox appear headed into the season with Clay Buchholz as the ace of the pitching staff… yes, that Clay Buchholz. The guy who makes J.D. Drew look like Cal Ripken Jr. is the best starter we have. The good news is that Porcello has a chance to take a big step forward this season (and I think/hope he will). Porcello has been in the Majors since 2009, but will turn 26 later this month. He was the fourth best starter in a rotation that had the 2011, 2012, and 2013 American Leaue Cy Young Award winners (Justin Verlander, David Price, and Scherzer), and he’s in a contract year. If Porcello becomes the pitcher I think he can be, and the Red Sox lock him up, then the Lester deal will not seem so bad. For now, though, it still hurts that an organization so smart can be so stupid with a pitcher any baseball fan could tell you was a perfect fit for them.

Lester is in a pretty good situation now in Chicago, reunited with Theo Epstein, who was the GM of the Red Sox when they drafted him, and they have a chance to make history. The downtrodden Cubs last won the World Series in 1908, and Lester and Theo have a chance to end more than a century of futility. More than anything, I’m thankful that this well done Photoshop job didn’t end up coming true. I guess it could always be worse.

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