Red Sox free agent targets: Boston should (re-)sign Jon Lester

Because this is Over the Monster, I hope I don't need to sell too many people here on the merits of Jon Lester. Lester's career with the Red Sox began in earnest as the team marched their way towards a second championship in four years back in 2007. Between that season and the time he was shipped away at the trade deadline this July, he was the best starting pitcher on the team by fWAR, rWAR, ERA, FIP and plain old wins. He has been the Red Sox' opening day starter every season since 2011. If you are looking for Madison Bumgarner-style postseason heroics, there is only one other pitcher in the game today who has had anything close to that kind of success in the World Series, and he did it with the Red Sox. If you are Red Sox fan, you should be a Jon Lester fan.

Of course, because this is free agency and because baseball is a business, the issue of whether or not the Red Sox should sign Jon Lester this winter is not simply a matter of the heart. His past performance has earned him the love of Red Sox fans but the decision to pay him the market rate (or more) this winter is not about the past, but the future. Jon Lester has been excellent, but will he be worth the price it will take to bring him back? Will he provide more value for that price than other top free agents like Max Scherzer and James Shields? And finally, should the Red Sox spend their money chasing baseball's riskiest asset, the premium free agent starter? I believe the answer to all three is yes.

To start with, the Red Sox' decision to chase a top-tier starter seems like a no-brainer. The team has an impressive array of young arms all closing in on the majors, but no clear number-one starter, and the only player in the rotation with a full season in the majors at this point is Clay Buchholz--possibly baseball's most enigmatic arm. The Red Sox rotation needs certainty and quality and while trading for an established arm is a valid option, the 2014 club's shortcomings on the offensive side make it difficult to sacrifice the potential of Mookie Betts or the power of Yoenis Cespedes for something that can be acquired with cash alone. Today's Red Sox are not the 2011 version and a single extravagant deal will not bring them back to the brink of financial collapse. The Red Sox have money to spend and adding one of the best arms available to head up their young rotation is the perfect way to spend it after all the late-season moves to bolster their offense.

Many smart people have been debating the cost of a win these past few years and though there isn't a complete consensus, the going rate seems to fall around $6 million a pop. A player like Jon Lester, who has averaged 4.5 fWAR per season, therefore commands around $27 million per season, with teams generally discounting that some because of the inherent risk to pitchers, the inevitability of decline, and the limitated number of opposing bidders at the top end of the market. MLB Trade Rumors sees Lester as the mid-point of the three top options with a deal on par with Zack Greinke's six-year, $147 million deal with the Dodgers. Scherzer already rejected one offer in that range from the Tigers.

Matt Collins already argued that the Red Sox should seek out the relative bargain of the three with Shields, but that could still mean committing to five years and $100 dollars, and that bet comes with bigger risk than the other two. If Jon Lester does sign for six-years and $147 million, performs at that three-year average just once and then declines a half a win a year, he will cost around $7.5 million per win. Considering the inflation rates baseball has seen in recent years and will likely continue to see until the television deal boom runs dry, that rate is just about market rate for the term of his expected contract. Paying market rate isn't great, but if the Red Sox are going to land an impact arm, they will pay that rate either in trade or in cash. If they don't pay it in trade, the real question is where the best chance for getting better performance than the market rate lies.

James Shields might be the lowest priced of the free agent options, but he is also the oldest of the three and while he has tempered the impact of his declining strikeout rate with improved command (much like Lester) he has also benefited from pitching in two extremely friendly home parks in his career in front of some of the best defenses in the game. His career FIP- numbers don't  compete with either Lester or Scherzer. Shields has also never reached the heights of performance that both Scherzer and Lester have. Lester has topped 6 WAR twice by both Fangraph's calculations and by Baseball References. Max Scherzer has done that in each of the last two seasons by B-R's figuring and come close by Fangraphs as well.There is an appeal to limiting the commitment the Red Sox take on with a signing this offseason, but I don't see a four-year deal happening for Shields and at five years the savings isn't enough to justify signing the player who has the least potential upside of the three.

Recent history shows that Max Scherzer is the best option available, but the case isn't as cut-and-dry as you might think. You see, Jon Lester was the best of the three in 2014, He had a significantly better ERA than both Scherzer and Shields and his FIP and xFIP were far better than Shields and just ahead of Scherzer. He was also the best of the three in the second half of 2013 by FIP and just a bit behind the Cy Young Award-winning Scherzer in ERA and xFIP. After stumbling late in 2011 and in the dark days of the 2012 season, Jon Lester has remade himself from an elite power pitcher who could survive high walk rates on the strength of his strikeout rates to an elite control pitcher who can still post a strong strikeout rate thanks to his cutter and curve. Almost every pitcher must make the transition from brash young thrower to skilled veteran pitcher as his stuff diminishes with age but not many do it as well as Jon Lester has to this point.

Photo Credit: Rob Carr

While Scherzer's last three seasons are better than Lester's, a closer look at the question of who is the superior talent complicates things. Lester was better in 2014, but not by much and variations like that happen. Those second-half numbers from 2013 blur the line even more.  There is no contest in 2012, when Lester struggled badly amid the chaos of Bobby Valentine and the post-collapse circus. But before that? Well, Scherzer was definitely not up to Lester’s level in 2007 when Lester was getting his first taste in the majors and Scherzer was still working his way through High-A and Double-A. He wasn't quite there in 2008 either because, as he was figuring out Triple-A and getting his first taste of show, Jon Lester was establishing himself as one of the best young pitchers in the game. Lester was far better in 2009, when he posted his first 6 fWAR season and in better again in 2010. And 2011. Did I mention 2014?

All told, Jon Lester has been better than Max Scherzer in five of the last seven seasons. There is an age gap, but it is just over six months, not the year that a quick glance at their season ages might lead you to believe, so we shouldn't just write off Lester's quicker rise to the majors (even with cancer slowing him down) and his earlier success as just a matter of being older.  Recent history favors Scherzer and that deserves the weight it will get in projections, but the gap in the underlying talent between these two pitchers is probably smaller than the gap in their contract size will be.

So while, Scherzer is the better pitcher right now, he may not be the best value. He is great, no doubt. He won the 2013 Cy Young Award and he was almost as good last season by both FIP and xFIP. His strikeout rate is among the best in the game and it is holding steady, while Lester has seen his dip and rebound. There is a strong case to be made that the Red Sox should sign Scherzer and one of my colleagues will be making it shortly. I am not arguing against Scherzer, just against the premium he will command. It sets the bar high and makes the inevitable decline more problematic for Scherzer than it will be for Lester. If the difference between Max Scherzer and Jon Lester is not quite as clear cut as public perception makes it seem, and the variations inherent in baseball performance make it close to an even-money bet as to which one will be better in 2015 and 2016, why would the Red Sox pay more for a guy who isn't the one they developed and managed all these years? Scherzer will get seven years at an even higher rate than Lester. The difference in their age is not enough to make much difference in their perspective decline rates, but the team that signs Scherzer will get an addition year of a pricey veteran who is no longer what he was in 2014. If there is a reasonable chance that Jon Lester will either provide equal value to Scherzer in the earlier years of the deal (and he just did that) or decline more gracefully (like so many crafty lefties before him) then he is the better option.

Factor in his experience pitching in Fenway, what he means to Red Sox fans and his unreal postseason numbers and that becomes even clearer. On their own, those factors are hardly justification for signing Lester, but given that his case is strong enough already, those things should matter. No other free agent will have the good will that Jon Lester has already earned from the Fenway faithful and when you are making roughly 3,200 teacher’s salaries over six years, that kind of thing can matter. If Scherzer struggles early, he will get killed in the press and in the bleachers in a way that Jon Lester probably won't. The excitement of a new player might be a welcome plot line over the winter, but the advantage that comes from all the information a team has on a player they developed and controled all the way to free agency as a better track record of actual results.

It takes a much clearer gap in talent than I see between Lester and Scherzer to simply write-off all the other factors that favor Jon Lester and still pay an even greater premium for the other guy. I won't be upset if the Red Sox sign Scherzer or Shields, because they are both great pitchers and they both fit the Red Sox most pressing need. They should be both be back-up plans, however. The guy who anchored the staff during their incredible 2013 season and pitched them to their third World Series Championship in 10 seasons should be the one to anchor their next championship team.

Just sign Jon Lester, guys. Seriously.

Do it. Do it now.