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As we head into the Thanksgiving weekend, the Jon Lester rumors are getting as hot as Craig Goldstein’s pie takes. The Cubs have supposedly offered a six-year deal worth more than $135 million, and are willing to go higher. There have been only seven $100-plus million deals handed out to pitchers on the open market since Kevin Brown broke the barrier in 1998, and just two of those pitchers (Brown and Cliff Lee) were past their age-30 seasons when they signed. Add in the fact that there’s never been an offseason in which two free agent pitchers both got nine-figure deals—as Lester and Max Scherzer are poised to do—and it’s shaping up to be a very spendy winter.

Lester provides a really interesting study as to what sort of pitcher, and what sort of career trajectory, is worth this type of money. Why do front offices deem Lester worthy of a deal that’s likely to open so many eyes?

It’s a complicated situation with Lester, who just two years ago suffered through the worst season of his career. The season was so rough that Peter Gammons questioned whether Lester would be happier outside of Boston (while now everyone is assuming he’ll take less money to return to Boston), others wondered if trading him was best for everyone, and some were questioning quite early in that season why Lester no longer looked like Lester.

But a lot can change in two years. I mean, two years ago at this time, Clayton Kershaw had just led the majors in ERA, Mike Trout had just led all position players in WARP, and the San Francisco Giants were still buzzing off a World Series Championship. Wait, let me try this again…

Take a look at how the 2012 version of Lester compared to the one we just witnessed:

IP

ERA

ERA+

K%

BB%

Lester – 2012

205 1/3

4.82

87

19.0

7.8

Lester – 2014

219 2/3

2.36

155

24.9

5.4

It’s not that odd to see a consistent player have a terrible season and then bounce back soon after. What is rare is to see a pitcher struggle as badly as Lester did in 2012 and have a career year soon after, a season that puts his firmly among some of the best walk years in recent memory.

Since 1998, there have been only four pitchers who have hit the open market coming off a season where they posted an ERA+ of 150 or better: Brown (164), CC Sabathia (156), C.J. Wilson (150), and Lester. Brown and Sabathia each blew away the biggest deals ever handed out to a pitcher at the time. Wilson earned a solid deal (five years, $77.5 million), even though he had just two seasons as a full-time starter under his belt.

If this were just based on his walk-year numbers, Lester would be in line for a deal that could challenge records. Here are the walk-year statistics for the seven pitchers who have received $100-plus million deals on the open market since Brown first broke the mark:

Age

IP

ERA

ERA+

K%

BB%

Jon Lester

31

219 2/3

2.46

155

24.9

5.4

Max Scherzer

30

220 1/3

3.15

127

27.9

7.0

Kevin Brown

34

244 1/3

2.38

164

24.9

4.7

Mike Hampton

28

217 2/3

3.14

142

16.3

10.7

Barry Zito

29

221

3.83

116

16.0

10.5

CC Sabathia

28

253

2.70

156

24.5

5.8

Cliff Lee

32

212 1/3

3.18

133

22.0

2.1

Zack Greinke

29

212 1/3

3.48

115

23.0

6.2

But here is how those same pitchers did in the three years prior to free agency:

Years

IP

ERA

ERA+

K%

BB%

Lester

2012-2014

638 1/3

3.65

111

21.1

6.9

Scherzer

2012-2014

622 1/3

3.24

127

28.6

7.1

Brown

1996-1998

727 1/3

2.33

172

21.3

5.1

Hampton

1998-2000

668 1/3

3.12

140

16.5

10.0

Zito

2004-2006

662 1/3

4.05

110

17.2

9.5

Sabathia

2006-2008

686 2/3

3.03

145

22.6

5.0

Lee

2008-2010

667 1/3

2.98

142

19.8

3.5

Greinke

2010-2012

604

3.83

106

23.3

6.2

Lester’s case for deserving an earth-shattering contract looks a lot less compelling when compiling his last three seasons; he sinks close to the bottom of the list. Of course, that includes his disastrous 2012, which, as rumored offers indicate, front offices don’t seem to be weighing too heavily. Likely, what’s buoying the offers from front offices are the four seasons as a full-time starter that Lester posted prior to that awful 2012 (when he averaged 32 starts, 203 innings, and posted a 135 ERA+). After that, they’re perhaps succumbing to a bit of recency bias, which pulls the offers even higher. And it’s hardly a stretch to imagine Lester getting significantly more than already rumored just based on 2014’s gaudy numbers alone.

Rob Arthur recently surmised that Victor Martinez could get a hefty contract based mostly on his great 2014. Soon after, the Tigers re-signed him at four years and $68 million, which doesn’t sound too crazy, until you take into account that he’s a month away from turning 36, a year removed from a merely average season, and two years removed from a season missed entirely. An economics student at Haverford College found that for position players (which, admittedly, are a different animal than pitchers) the walk year is overweighted, and less recent history underrated, by MLB front offices. “The fact that the free agent market does not behave rationally is certainly fascinating, and likely relevant to industries outside of the sporting world, especially those where performance indicators are noisier,” the author concluded. Heck, there have even been suggestions that how a pitcher performed in just his two most recent starts can dramatically alter how much a front office is willing to offer in a trade.

Add in the fact that Lester checks all the boxes that front offices normally look for outside of the stats—great health history, impressive makeup, leadership in the clubhouse and on the field, strong mound presence—and everything starts to point to the bidding just getting started.

So if initial reports that the Red Sox had offered Lester somewhere in the $110-120 million neighborhood over six years seemed low, your instincts were right. If you thought it was high, well, okay, you were probably wrong again! And if you’re starting to get queasy by the numbers being thrown out there now, it’s probably wise to swig some Pepto and buckle in.

But the bottom line is, the man is about to get paid. Lester still has a meeting with the St. Louis Cardinals, the San Francisco Giants just entered the picture, and the New York Yankees have been quiet, but are always hovering. There’s a chance that a $25 million AAV will look like a bargain when all is said and done.

Special thanks to Brendan Gawlowski and Jeff Euston with assistance on research for this piece.

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bigchiefbc
11/26
It was reported overnight that the Sox have upped their offer to 6/135-140.
Dodger300
11/28
I realize that when you "check the box" for good health you are talking about Lester's arm.

Even still, as my stepson is, similar to Lester, also in remission from non-Hodgkins lymphoma, I am well aware that one must remain vigilant, as this disease can unexpectedly come back some years later.

I am thrilled for Lester that he has been in remission for several years and hope that always remains the case for him. He's a good pitcher and seems like a great guy. In our free market system has earned the big contract he is about to sign.

But when ones health history includes cancer, I don't think you can ever "check the box" for good health. There remains some risk involved going forward.