Mistakes In July Have Red Sox Reeling This Winter, Especially With Jon Lester Choosing Chicago Cubs In Free Agency

December 10, 2014

By Matt Straub


It could have been so much simpler. The Boston Red Sox didn’t lose a desired free agent, they watched the first domino fall in what will be a series of unfortunate events caused by their rash judgment in July.


Patience is a virtue, and Boston’s lack of it in a bad month will cost them for years to come.


Let’s start the discussion about where the Red Sox go from here after Jon Lester ended his excruciating negotiation by signing with the Cubs while you were sleeping late Tuesday night with a brief history lesson.


It was July, and the Red Sox had Lester and John Lackey. The team was nine months removed from having won the World Series, but the 2014 season had gone up in flames for a variety of reasons. Boston already knew it needed a third baseman and perhaps another outfielder, an indictment on their winter of 2013 since they already had too many outfielders to begin with but still felt they needed another good one.


What the Red Sox had was pitching. Lester, Lackey and a host of young arms were going to make up a strong rotation going forward. Despite Koji Uehara’s collapse late in 2013, he was still the best closer in baseball over the last two years, and Andrew Miller was emerging as a great second arm in the pen.


All Boston had to do was wait until the winter, get Pablo Sandoval (which they’ve actually done), perhaps add a middle of the rotation pitcher for depth, and try again in 2015. All Lester and Miller would have cost was money, which would be easy to pay since Lackey was going to make a laughable $500,000 in 2015 thanks to a clause in his contract which kicked in when he was hurt a couple of years ago. Even if the Red Sox gave him more to make him happy as part of an extension, it would have been less than market value.


Instead, they hit the reset button, blew the whole thing up and decided to start over in the winter. What they didn’t realize was how much worse off they would be by doing so.


If the Red Sox decided the core of the 2013 team couldn’t win again, it speaks volumes about how poorly the team is being run. After all, 2012 was a disaster, as was 2014. If 2013 was a fluke, then the Red Sox hadn’t been a well-built team since the summer of 2011, when they were the best team in baseball before their historic collapse. Let’s put that aside for now, however, since it could have been fixed.


Suddenly, Lester was in Oakland. Lackey was in St. Louis and Miller was in Baltimore. I wrote at the time about how much I liked Boston trading for major league players instead of prospects, something which could revolutionize the trade deadline in years to come.


I was as fooled as the Red Sox were.


Boston got Allen Craig and Joe Kelly for Lackey and Yoenis Cespedes for Lester. Regardless of whether the team had outfield issues or not, it seemed like a decent haul at the time. Kelly is a solid middle of the rotation pitcher while Cespedes was a good rental player for a year and a half and Craig had been good a couple of seasons ago.


In the end, however, the moves proved disastrous. It took Boston two months to decide they didn’t want Cespedes for the long term, and the typical Red Sox smear campaign for players heading out the door was on. The Sox will trade him, perhaps as soon as this week, for some pieces, but probably not game-changers.


Craig was terrible during his stint in Boston and could also be on the move, but the Sox might give him a chance to win a spot in the too crowded outfield in the spring. Kelly is a solid pitcher, but not an ace by any means.


And so Boston went into this winter seeking two top-level pitchers to fill the voids left by Lester and Lackey. With Sandoval and Hanley Ramirez, the winter’s shocking and unnecessary free agent signing, Boston had retooled the offense and now just needed the pitching to contend again. You know, the pitching they had before they traded it away.


The plan was to bring back Lester as a free agent, spending some $30 million more than they would have had to if they had locked him up before the season as Lester had requested. But hey, it’s not our money.


Then Lester went to the Cubs and the plan was ruined. Now Boston will likely have to trade half the farm system for Cole Hamels or get into a bidding war over Max Scherzer, a guy they didn’t want as much as Lester.


I know it gets complicated, so let’s simplify it: Boston could have kept Lester, but instead traded him for a guy they will now swap for a pitcher who isn’t as good as Lester. To make up the difference, they will trade coveted minor leaguers for someone like Hamels. Boston is going to give up its return for Lester and more from its system for two guys (they hope) who won’t be as good as Lester, who didn’t want to leave in the first place.


In Lackey, Boston had the second pitcher they now seek. For him, they got a lesser pitcher and an injured player at a position they don’t need.


Oh, and Miller is a Yankee.


So what now? Boston will get its ace through a trade. To be fair, I didn’t want to give Lester, who I have written many times in this space is really a good No. 2, the money he got. It is, however, hard to justify losing a beloved player who won a lot of games for you and ending up with either lesser players or a gutted farm system to replace him.


If Boston ends up with Hamels, Justin Masterson and someone like Johnny Cueto, they will have enough arms to piece together a rotation which may contend. That, however, is a lot of ifs and maybes. If the Red Sox hadn’t overreacted in July, they’d have Lester, Lackey, Sandoval and their entire farm system, which could have added further depth this week.


Things could still work out, but the Red Sox are back in panic mode with Lester gone. They will spend the rest of the winter scrambling to make up for the mistakes they made in July.


It didn’t have to be this way.


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