Repeat after me: Jon Lester is a Chicago Cub. Repeat after me again: Jon Lester was an Oakland A's free agent. Accepting these two basic facts is the first step towards understanding how the Red Sox were unable to bring one of the best left handed pitchers in team history back to Boston.
My simple analysis here is that I would have been happy if Lester had come back, even if the Sox were willing to match the $155 million contract he received, but I am not upset that he didn't return. I think there is a very healthy debate to be had over whether or not bringing him back on a six year deal was the right move at all, let alone one that will pay him over $25 million a year.
Since all the radio discussions have started/focused on the contract extension negotiations in March, I guess that is where I will start too. I will get this out of the way by saying that in making a 4 year $70 million offer to open negotiations, the team basically killed its chance at extending Lester for the notorious "hometown discount." I definitely don't think it killed their chances of signing him at all, but it meant he was going to test the waters to see what his market really was.
The thing is, in March 2014, his value shouldn't have been crazy high. Let's play a little game of player A and player B (granted I am cherry picking here; the analysis for long term contracts is much more nuanced here but it is illustrative of how the Red Sox could have started with 4 for $70).
From 2012 to 2013:
Player A: 24-22 record, 4.28 ERA, 418.2 IP, 97 ERA+*, 1.34 WHIP, 2.54 K/BB ratio
Player B: 25-24 record, 4.08 ERA, 390.1 IP, 95 ERA+*, 1.29 WHIP, 3.12 K/BB ratio
*ERA+ is a players ERA compared to his league average taking into account whether he pitches in a pitchers or hitters park. Player A is 3% worse than average; Player B is 5% worse than average.
Player A is Jon Lester; not exactly a great performance in the time leading up to the extension talks. Player B is Ricky Nolasco. Nolasco was a free agent after 2013 and he signed a 4 year, $49 million contract with the Minnesota Twins that off-season after posting very similar numbers to Jon Lester the previous two years.
Now, there are several differences that make Nolasco worse at that particular time than Lester. Nolasco was a year older (though when their new contracts start they would be the same age) and right handed. Lester had just had a dominant post season run while Nolasco pitched in one playoff game and gave up 3 runs in 4 innings. Lester also had many years of success prior to 2012 where Nolasco was below average most of that time. Nolasco pitched in the easier National League in a pitchers park while Lester was in the AL in a hitters park (though this is taken into account in ERA+). On the other hand, Nolasco was a free agent and free agent deals are always going to cost more than extensions before free agency.
I am not saying Nolasco is the equal of Jon Lester. In fact, offering Lester 4 for $70 shows that the Sox agree with that. All I am doing by pointing this out is that Lester's bargaining position wasn't as strong at the beginning of 2014 as people think. Until August 6, 2013, Lester had a 4.52 ERA before he got hot for 2 regular season months and one playoff month. With 2 years of data showing diminished performance and a much diminished strikeout rate, it was fair for the Red Sox to wonder whether it was smart to throw huge money at the guy for the next 6 years, all of which would be in his 30's when players typically decline. The team knew 4 for $70 wasn't going to get it done and maybe that was the point. Maybe they never really wanted him back, but I will get to that in a minute.
Lester headed into the 2014 season without a new deal. He bet on himself and it was clearly the right decision. By any measure (ERA+, WAR, FIP, ERA, K/BB) he had the best season of his career. The success seemed to show that maybe he made some kind of adjustment in his approach or mechanics in the middle of 2013 so this probably wasn't a fluke (seems like he ditched his changeup and threw his cutter more). Unfortunately for the Red Sox, Lester couldn't help the Red Sox score any runs so his success on the mound was completely neutralized. When the trade deadline rolled around, the team was faced with a choice: hang onto Lester and risk losing him for a late first round draft pick, or trade him for future assets. The Sox chose the latter and it was absolutely the right choice.
Some people believe that by trading him, the Sox hurt their bargaining position with him in free agency. I think this is completely false. Forgive me for temporarily speaking in hypotheticals and playing armchair psychologist, but by offering Lester 4 for $70, the team ended any hope they had in extending Lester or getting him for a major discount. Trading him at mid-season did not hurt their position whatsoever because he was not going to sign an extension and the Sox were going to be treated like any other team no matter what. If anything, the Sox did Lester a favor by giving him a chance to win another ring. This says nothing of the fact that the team traded 2 months of a player they had no use for for an extra year of a middle of the order bat plus a second round draft pick. It was a great trade for the Sox.
When the off-season started, the Sox began their pursuit of Lester pretty quickly. Reports said the first offer was 6 and $110 million, which seemed like another offer that meant the team didn't really want him back. But this wasn't a take it or leave it offer. When negotiating, one side offers low and the other side counters high. Eventually you meet somewhere in the middle. The Sox did nothing wrong starting at this level. They continued to increase their offer up to the end. John Henry flew to Lester's house to meet with him. These may have been PR moves, but at the end of the day the team made a pretty large offer to him and if he had accepted it then he would have been our Opening Day starter with no regrets. The Red Sox were one of two finalists for his services because Lester wanted to pitch here despite the low-ball March offer, the mid-season trade and the initial low offer to start the off-season. He was not insulted by anything the team did, nor should he be.
$135 million over 6 years is a lot of money and you can easily argue that is what Lester is worth. You can also argue that he is worth $155 million over 6 years. You can also argue that no pitcher in his 30's should get a 6 year deal. All arguments would be valid. Different teams have different methods of evaluating talent and all the wicked smart people in the Boston front office determined that Jon Lester was at most worth $135 million over 6 years. You could say that $155 million is only an extra $3 million a year so why not just give it to the guy if that's what would get it done, but where does it end? A team has to trust it's analysis and set a ceiling for what it is willing to pay. It is possible that the team knew that $135 million was just enough to be competitive but not actually get the job done, but that's a dangerous game to play. If you don't want a player for that much money you shouldn't offer it just in case he accepts.
Let's also be clear about something: this is a crazy risky deal. Pitchers are so unpredictable because of injury. Most pitchers get injured, even ones that looked durable when they were younger. CC Sabathia was a better and equally durable pitcher when he signed his big contract at age 28. The first 3 seasons of that deal worked out well, but then he under performed greatly in season 4 and was injured in season 5. He still has 2 years left and is going to be 34 next year. I think there is a much greater chance that Lester is bad for the last half of this deal than he is good, though some people seem to be ok with that. But why? Why just accept that for 2 or 3 years of a contract you are going to burn $25 million per year and it won't matter? It will matter! That's still a lot of money that you can't just ignore. Look at the Yankees this past year. They had all those expensive arms that were hurt or not effective and there was nothing they could do to fix it. Teams do have a limit on what they can and want to spend.
This is the problem with getting hung up on any one player. Yes, Jon Lester would have made the Red Sox a better team next year. He was the second best pitcher available in free agency and far better than any pitcher the team had under contract at the time of the negotiations. But he was not the only pitcher available and he was not the only pitcher that was better than what the Sox had at that time and signing an "ace" (which is still debatable whether he even is one) is not the only way to make your team better. You can improve the offense (which the team did), the bullpen (which is still possible) or the rest of the rotation where you have crappy options (which the team did). You can also realize that it is only early December and there is plenty of time to make other moves.
In sports, players are really assets to the front office. It's weird to say because as fans we love the human element. It's what brings us to the ballpark. The thrill of victory and agony of defeat. But when you are building a team, each player is essentially a number on your ledger of wins and losses. If you get hung up on specific players rather than the wins and losses you end up overpaying in dollars or prospects when you could have shifted strategies to improve your team just as much in another way. The Sox missed an opportunity to improve their roster at that time with just one player, but, as you will see, they have since found other ways to improve in 2015 and maintain a more flexible future.
We will all miss Jon Lester. He helped bring 2 World Series to Boston. He recovered from cancer to become one of the best pitchers we have ever seen in Boston. He helped bring chicken and beer to the clubhouse (oh wait, we are supposed to hate him for that right?). He was a very intense competitor. He threw a gorgeous cut fastball. He was a three time All Star. He has an outside chance at the Hall of Fame. The Cubs got an excellent player who should help accelerate their bid for contention. But in the long run, I think the Boston Red Sox will be better off.
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