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Is Jon Lester worth $150 million to the Red Sox?

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With word out once again that Jon Lester is looking for around $150 million in a new deal, it's time to figure out where the Red Sox should draw the line.

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Jon Lester reportedly wants to earn $150 million for his next contract. This isn't news, necessarily: Ken Rosenthal reported during the 2013 World Series that at minimum Lester was looking for $146 million as a free agent. If you were reading this site at that time, you already know this, even if you had forgotten. A week ago, when rumors of the Cubs submitting an offer for "north" of $135 million came out, various sources reported Lester was still looking for $25 million average annual value on his new deal -- $25 million a year for six years is $150 million. Then, on Monday night, Marino Pepén reiterated this $150 million figure on Twitter, and a whole lot of people seemed to notice for the first time that this is likely what it's going to take to secure Lester's services.

The dream of re-signing Lester for a team-friendly $120 million or so died the moment he was dealt to the Athletics. That's not to disparage the Sox for dealing Lester -- they moved him because it became unclear if they would be able to retain him on their terms, and wanted to get something that could help them now instead of later, as a compensation pick for letting him walk would netted them. You can criticize the Sox for not making something happen while the idea of a team-friendly discount was on the table, but that period of time in the Lester negotiations is well behind us all.

Lester is probably going to cost $150 million over six years, because he has no shortage of suitors to push things to that level and is a relative bargain at that price. It's difficult to believe that anything that costs $150 million could be a bargain, but consider this: Max Scherzer has already turned down a six-year, $144 million deal in this calendar year, as the Tigers tried to extend him before the 2014 season. Scherzer is going to hold out for more money than that, and will likely get it from someone in January the same way the major Scott Boras' clients before him have managed to. Lester is at least as good as Scherzer. Felix Hernandez, Justin Verlander, and Clayton Kershaw make between $175 million and $210 million guaranteed over the life of their deals, and for all the risk and concern over his body holding up, CC Sabathia managed to score a $161 million extension. You could argue the first three are all better pitchers than Lester, but that's why they're making significantly more than Lester is aiming for to begin with.

The dream of re-signing Lester for a team-friendly $120 million or so died the moment he was dealt

Cole Hamels will cost fewer dollars than Lester, but can only be acquired through a trade that will require at least one impact prospect, maybe two, and will still be owed a $22 million per season commitment on top of that over the next five years. James Shields will sign for fewer years than Scherzer and Lester given he's a few years older, but he'll also end up pulling in over $20 million per year, and both he and Scherzer will require a compensatory draft pick in 2015, unlike Lester. Ergo, Lester is a relative bargain from basically any ace-related angle.

Is $150 million too much money for the Red Sox to invest in one pitcher, though? It depends on the pitcher in question. It's too much for Shields, as he would be 38 years old in the final season of a six-year, $150 million pact. It's not too much for Scherzer, but as stated, he's going to end up costing more, and possibly significantly more. It's probably not too much for Lester, when you consider he's two years younger than Shields, a better pitcher, and the Red Sox have the budget to work him in. Bringing in Lester means they will have blown by the luxury tax threshold of $189 million for 2015, but the team has already claimed they don't mind doing that every now and then, so long as it's not a consistent theme of their budgets. In the future, nudging up against the tax threshold won't be as much of a concern, either, as free agents take off and prospects like Blake Swihart, Henry Owens, Eduardo Rodriguez, and eventually Manuel Margot and Rafael Devers move up to inexpensively fill in the holes.

Eduardo Rodriguez
Eduardo Rodriguez isn't a likely ace, but there are four other rotation spots to fill. (Photo credit: Kelley L Cox-USA TODAY Sports)

The Red Sox are already at $152 million in payroll for 2015 even before signing Lester or tendering contracts to any of their arbitration-eligible or pre-arb players. In 2016, though, those commitments drop to $83 million. Add in $25 million for Lester, as well as David Ortiz's $10 million option and maybe another $16 million to re-sign Mike Napoli since first base options are limited, and those commitments jump to $134 million. The Red Sox would have no major holes to fill, however, as their only major losses would be Shane Victorino, who maybe doesn't have a place in 2015's outfield, non-closer reliever Edward Mujica, and Clay Buchholz should he be a disappointment once again in 2015 and have his $13 million option declined -- that's a hole that presumably can be plugged with Owens or Rodriguez, if it hasn't already been by next offseason. If Ortiz ends up costing more because he hits his incentives, great! If Buchholz pitches well enough to have his option picked up, even better! Even if the Sox retained Buchholz, that's still $42 million to play with under the tax, and all of the arb and pre-arb players won't cost $42 million.

In 2017, the luxury tax will presumably be raised since a new collective bargaining agreement will have been negotiated. The Red Sox begin 2017 with $78 million in commitments, though if we add in Lester, Ortiz, and Napoli once more, they're at $128 million. They'll lose Junichi Tazawa and Buchholz if they haven't already, as well as Koji Uehara. Relievers can get expensive, but remember that at this point, the Red Sox have also probably been converting their lesser starting pitcher prospects to relief, and have a more inexpensive pen than they do at present, one that can shoulder the load created by the loss of these arms. Losing Buchholz might not be a tragedy, either, given his up-and-down nature and the fact that in 2017, Owens and Rodriguez are likely established major-league arms, or, at least, that's the plan. Once again, there are limited holes to fill, and the Red Sox have money to play with well under the luxury tax threshold. Some of those inexpensive prospects might not work out, but that's all the more reason to have someone reliable and established like Lester on the roster.

In 2018, those initial commitments drop to $70 million. In 2019, $45 million, and in 2020, $32 million. The players who are low-cost now will be a bit more expensive through arbitration, of course, but even with that, the Sox will not have added much in the way of new costs through free agency, meaning there is plenty of room both now and in the present for Jon Lester at $25 million per year.

Maybe Lester won't be the same pitcher at 34 or 35 that he is right now. Maybe he won't be worth $25 million in 2018 or beyond. Teams don't sign major free agents believing this will happen, however: they sign these elite players in the hopes that the first few years of the deal will more than make up for any downturn on the back end. Inflation will help take care of most of the rest, too, but the real key is that the Red Sox will be a better team for the next few years with Lester at the head of their rotation than they will be without. The cost is high for that, but someone has to do it, and Lester is the relative bargain of the bunch. He's worth the $150 million it seems like it will take to acquire him, and all we can do is hope it's the Red Sox who are most aware of that fact.

All salary data taken from Cot's Contracts.