By Andrew Oak
The Lester deal is for six years and $155 million dollars. The Sox final offer was six years and $135 million dollars. Was the difference of $20 million dollars the deciding factor in signing with Cubs, possibly, but I think there is more to the story.
Over the past few days, there were multiple rumblings from the MLB Winter Meetings that Lester was deciding between either the Giants, Cubs and Red Sox. Honestly, i'm not a huge fan of the Winter Meeting 'rumblings' because owners and managers need to provide leverage to the media and the fabrication of some stories lead to false rumors instead of facts. Having said that, Lester's agent said that he will be at the negotiation table and make his decision that would come down to the last minute. Initially, I took it with a grain of salt because I'm saying to myself, "150 Million or 160 Million? WHO CARES, just go with your heart and come back to Boston." When I started to go in depth with these comments, I ended up with this conclusion. There was no way that he is coming back to Boston. Since it all came down to the contract, I had a feeling the Red Sox were going to lose the fight because when the Sox offered a 4 year, $70 million dollar contract extension prior to last season, there was going to be some issues in negotiations.
If Jon Lester wanted to come back to Boston, he would have done more on his end to make it happen. Therefore, the decision to choose the Cubs over the Red Sox was because of what happened 'behind the scenes' in contract negotiations.
The contract, first reported by ESPN's Jayson Stark, is something like this.
"The deal includes a signing bonus of $30 million to be paid over the life of the contract and a full no-trade clause. Lester will earn $145 million between his base salary and signing bonus and receive either a $10 million buyout after six seasons or a $25 million vesting option for the 2021 season that could bring Lester's total take to $170 million. The option would vest if Lester pitches at least 200 innings in 2020 or at least 400 in the 2019 and 2020 seasons combined. Lastly, he also gets access to 25 hours of personal flights on a private plane per year."
Let's be honest, I never thought a pitcher of this stature (homegrown talent, ace, multiple WS championships) would be weighing the option to join the Chicago Cubs over the team that he has practically spent his whole career with. I just never saw it coming. As much as Lester still loves Boston, the fact that he would rather spend the rest of his career in Chicago is almost insulting. This is what I call the 'Theo Epstein' factor.
There is no doubt in my mind that Lester was sick of Red Sox management and wanted a change of scenery. If i put myself in Lester's shoes, I understand how he makes this decision. He saw what Theo did in Boston and got them out of the basement and ended a 86 year World Series drought and now Lester wants to be a part of history by potentially ending the Cubs drought as well. When I look at the Chicago Cubs from the top down, Epstein, Maddon, Lester, that is something that is tough to assemble. Having an "ace" in all three aspects of a baseball organization GM, Coach, SP is a nice combo to have to compete for World Series Titles. What's confusing to me is why Lester chose to be so secretive during the 'negotiations'. We all heard that he was willing to take a 'hometown discount' to remain with the Sox, but apparently Lester wasn't the number one free agent on the Boston Red Sox's list.
For instance, the Red Sox started the offseason by signing two huge bats, Sandoval and Ramirez, to insert into the lineup. Did that not catch Lester's attention? Did he find it insulting that the Red Sox were more focused on bats rather than pitching? After spending almost $200 million dollars on two position players, you would think the Sox would cough up another $20 million to keep Lester right? Was it a scenario that the Red Sox just misread the free agent market entirely? This is where I think the wheels fell off the cab completely. Jon Lester thought he was more valuable than the Red Sox thought and obviously the Red Sox did not value him as highly as other free agents. Granted, SP only pitch in 30-35 games a year. So I do understand why (any organization) would rather pay a position player who plays 160 games a year, rather than a player who plays every fifth day. That is somewhat justified from a management perspective.
Now that Lester is gone, where do the Sox go next? Well, lets start with the options. You can either sign free agents, make trades or stay with what's in your farm system. The Sox starting rotation currently stands like this (roughly),
2. Joe Kelly
3. Rubby De LaRosa
Without Lester, do you really want to depend on Clay Buchholz as your ace. Buchholz has shown signs of becoming an number one, elite starter. His two biggest issues so far in his career have been staying healthy and being consistently good throughout a full season. If those are your two biggest issues, than in my eyes, you shouldn't be an ace. Therefore the next Sox move should be going after a different color Sox and go after Chris Sale.
Sale is a power lefty with an affordable contract. After the White Sox have made some moves to acquire some pitching, are they willing to deal away Sale to get more depth players. Given the way of how bad the White Sox were last year, they should consider it. Chris Sale, to me, is a much better pitcher than Cole Hamels and James Sheilds. If the Red Sox end up with Hamels or Shields instead of Sale, I'll be content, but not satisfied. Preferably, the right move would be to find another "ace", but I'd much prefer a trade rather than throwing around more $$ on a SP.
Even if a trade for Sale or Hamels does not work, the FA pitchers on the market wont replace the production of Jon Lester. The shock of Lester not coming back to Boston still might hit hard to the average Boston Red Sox fan, but once spring training starts, I think the Sox will be in formidable position, still, to contend for a title because of the depth we have on offense and defense. There are obviously a lot of moves to make because of the stockpile of OF's and young SP that we have can transcend a franchise's youth movement.
Ultimately, the Red Sox dropped the ball on Jon Lester and the fact that ex-Red Sox GM Theo Epstein took him away from you, will make the Red Sox react in some type of way, trust me. The need for pitching is still high on the Red Sox priorities, but after missing out on Lester, trading away prospects to shape your roster is the proper and correct move because it was only two years ago that we were up in arms for the Sox throwing around money to impending FA's. Now they we have thrown away money to Sandoval and Ramirez, I think it would be unethical to sign another top SP while unloading another $100 millions dollars.
There will be more breaking news that will come form the Jon Lester negotiation "fallout", but in the meantime, lets just pray that the Red Sox get it together and react RESPONSIBLY to the loss of Lester. It would be a shame if we spent more money on another pitcher other than Jon Lester.