NEW YORK -- If they want to keep Jon Lester -- truly keep Jon Lester -- the Red Sox are obviously going to have to do better. Potentially a lot better.
According to a major league source, the Red Sox' most recent offer to Lester regarding an extension past the $13 million he is making in 2014 was for four years at $70 million.
That isn't going to get it done. The Red Sox had to know that.
This isn't Dustin Pedroia sitting two and a half years away from free agency, or the reality that was Jacoby Ellsbury awaiting his seven-year, $153 million offer from the Yankees. This isn't even the Lester who signed a five-year, $30 million back in '08.
This is a player who has players and contracts that he can compare to his own situation, and someone who is confident in possessing a pretty healthy understanding of the process.
"That's what you go through now. You go through all the information," Lester said. "You gather all the comparables. You gather all the stats you can, and you go into a room with those guys with all their information and you try to hammer it out. Sometimes you're able to see eye to eye and other times you're not so you work through those problems and hopefully you end up at a happy medium."
But despite the level-headedness and desire by the pitcher to stick around, this is the sort of progression which won't lend itself to happy mediums. The Red Sox had an opportunity to be aggressive before calling it quits at the conclusion of spring training, and they didn't take advantage of it.
Sure, it's understandable if the Red Sox want to shoot for four years. Lester will be 31 years old when his new contract kicks in.
But what happened to the strategy the Sox implemented prior to '13, paying more annually for a year or two less? That worked so nicely in the free agent market. And now they have the opportunity to pursue that course even before other teams get involved, but they instead reverted back to the same strategy implanted for Ellsbury -- making him an offer he very easily can refuse. (In the case of Ellsbury, the team made an offer with which it could be comfortable of five years, $80 million -- not a realistic possibility for getting a deal done.)
The "overpay for less years" approach would also seem to be a good fit here considering how manageable the Sox' financial commitment is to the rest of the starting rotation.
Thanks to John Lackey's $500,000 option for '15, Clay Buchholz's deal that won't pay him more than $13.5 million through '17, Felix Doubront having three more years until free agency and the Henry Owenses of the world not even starting their major league clock yet, even a $20 million-plus-a-year commitment to Lester would put the entire starting five under $50 million for each of the next three seasons.
Instead, the Sox made an offer to Lester that was basically the same as the one that the team used to extend Josh Beckett four years ago when the starter signed a four-year, $68 million extension. The problem is two-fold: That was four years ago, with salaries having undergone considerable inflation since then (to the point where a player with comparable career numbers like Max Scherzer could walk away from a reported six-year, $144 million offer from the Tigers), and Lester has a better, more consistent track record than did Beckett when the Sox extended him.
If nothing else, think about the dynamic if Lester accepted the offer. Part of any Major League Baseball contract (sometimes unfortunately) is how it is viewed by the Players' Association. The pitcher is well aware of that part of the equation, and has been for some time. He is not going to be bound completely by how any new deal looks, but Lester will factor in what any agreement might have on the next group of high-priced big league pitchers.
And four years, $70 million -- when Adam Wainwright signed a five-year, $97.5 million deal last year, a contract that kicked off in the Cardinals pitcher's age 32 season -- isn't exactly going to be moving things forward for those successors for whom Lester will become a key data point.
"At the end of the day, we're part of the union. They have to respect your decision," he said. "I don't want to be the guy where you sign a deal and then a guy like [Felix Doubront] comes up and says (sarcastically), 'Thanks Jon for helping me out.' That's the tough part. You've got to balance what makes you happy and still have to take into account where the Players' Association is, you have to take into account the market and what's fair, and then you do what makes you happy. If you're a little bit below market value and it makes you happy, who cares? If you're astronomically below market value, then that's where you need to look at it. Then you have guys who are fortunate enough to set the market. They're going to go beyond."
And this last offer was a whole lot closer to astronomically below market value then setting the market.
Lester is clearly his own man, as was evidenced by the willingness -- even stated desire -- to accept a hometown discount. But he is also armed with the realities of living through a contract year.
"I feel like when you have information and you have those deals in place it makes it easier," he said. "You have to take all the information you can for your particular case. I think if you're educated, and you make an educated decision, I don't think you can ever go wrong."
So knowing Lester was ready to give them a window to find a somewhat team-friendly happy medium, why wouldn't have the Red Sox come in more aggressively?
They declared their desire to keep Lester, and they also must know what can happen in the world of free agency. When you start introducing other teams, the annual average values of such players as Cliff Lee and Zack Greinke (more than $23 million per season) start being introduced.
Maybe the Red Sox are banking on Lester's desire to stay, remembering the case of Mike Lowell, who turned his back on four years with Philadelphia in favor of three more years in Boston. Perhaps they are of the mind that Lester is ultimately replaceable at the top of the Red Sox' rotation. Or maybe the Sox feel they can use '14 to have a more precise sense of their comfort level in investing in Lester -- perhaps avoiding a scenario such as the one they had with Beckett, where they extended him at the start of 2010 only to see that year give way to a host of injuries that ultimately crushed his performance, and that likely would have resulted in a lesser deal for him as a free agent than the one the Sox gave him almost a year before he was slated to hit the open market.
But all are potentially dangerous propositions.
This is Lester's last big contract, and if some team wants to blow the Red Sox' offer out of the water -- far beyond just adding an extra year -- it will be tough for even a player as loyal as the lefty to turn that down. And waiting for the development of any of these young pitchers to turn into the guy who can survive in the American League East while stepping up on the biggest of stages can be an uncomfortable process. Think about how long it took Lester to become Lester.
Right now neither side has any intention of rekindling negotiations. After learning of the Sox' offer it's hard not to think that an opportunity was missed. The Sox might not have been able to get a deal done, but this was the equivalent of not even putting on the cleats.
"We're all hopeful, absolutely," Lester told reporters Saturday. "Like I've stated before, I would like to think what they've said is true as well. I want to be here. They said they want me here. So just at that particular time, things didn't really pan out, didn't work out. When the time comes, we'll sit down again and see where we're at then."
It will undoubtedly change the next go-round. But by then will it be too little, too late? It's all part of the conversation thanks to what might have been the Red Sox' missed opportunity.