How Will Jon Lester Age?

It’s Winter Meetings time, so that means the ratio of rumors to actual stuff happening is exponentially high. Some modestly sized moves have happened, however, and the possibility of something really big is in the air. The one big shoe that could drop at any given moment is the signing of lefty Jon Lester, most likely by one of four primary suitors: the Red Sox, Cubs, Dodgers or Giants. Where might he head, how might that destination treat him, how much money might he earn, and how wise of an investment might that be? Let’s answer those somewhat loaded questions as best we can.

When I began my baseball career as an Area Scout with the Brewers, I worked closely with a part-time New York City scout named Ed Fastaia. He was a tireless worker, a good friend, and he took great pride in having the Greater New York area locked down tight. The Bayside Yankees were a premier tournament club for high school players during this time frame, so they were a must see during the summer time.

Ed spoke of how he checked in to see the club early one summer to make sure his early follow list for the next year’s draft wasn’t missing any key names. He experienced one of those “wow” moments that every scout hopes for; he was the only scout there, and saw this unfamiliar tall, projectable lefthanded pitcher flashing now plus stuff. Since the club was usually comprised of players from the Northeast, he thought he had a scoop. After speaking with the coaching staff, he learned that this ringer was actually a Pacific Northwest kid who had headed east for the summer – a kid named Jon Lester. He made sure the office was in the loop, kept tabs on him, and went back to the business of searching for prospects from his own area.

Lester was then drafted by the Red Sox in the 2nd round of the 2002 draft, and signed for an overslot bonus. Though his minor league performance was inconsistent at times — 32-31, 3.33, with less than a strikeout per inning, albeit perennially as one of his league’s younger arms — Lester got partial-season auditions in the Sox rotation in both 2006 and 2007 before taking a regular turn for good in 2008. He’s started between 31 and 33 games per season ever since.

There are an awful lot of very good reasons why Lester is about to become a very rich man. The aforementioned durability is certainly one of them. His lefthandedness is another. His ability to be a solidly above league average performer while pitching his home games in a hitter-friendly environment is yet another. Is he, however, the type of guy to whom you would comfortably give a $150M+ contract, over as many as seven years? After all, he was a below league average performer as recently as 2012, and not that much better than average in 2013 before his stellar 2014 campaign. With all due respect, this isn’t quite Felix Hernandez or Clayton Kershaw we’re discussing here.

To get a better feel for his present true talent, let’s take a look at Lester’s outcome frequency and relative production by BIP type data compared to MLB average for 2014, both before and after adjustment for context. First, the frequency info:

Unless you’re a top-of-the-scale contact manager, you’d better excel at maximizing strikeouts and minimizing walks if you’re a starting pitcher in search of a long-term mega-contract. Lester meets this standard, with K and BB rate percentile ranks of 80 and 16, respectively. His K rate has been better in the past, but his 2014 mark still fits in nicely compared to career norms. The low BB rate represents a major breakthrough that bodes well for his future; it’s by far a career best, after four consecutive seasons with BB rate percentile ranks higher than MLB average.

Lester also induces a solid share of free outs from popups; his popup rate percentile rank of 75 is well above average, and this marks his third time in four years at that level or higher. Lots of K’s and popups coupled with few walks gives Lester plenty of margin for error with regard to contact authority. Interestingly, Lester has evolved into much less of a ground ball pitcher than he once was, as his 2014 fly ball percentile rank of 50 is a career high, and his ground ball percentile rank (36) is by far a career low.

Standing alone, that doesn’t sound like a positive development, especially for someone playing his home games in an extremely fly ball-friendly venue, Fenway Park. We’ll learn whether that is in fact the case as we gauge his contact authority allowed by examining his production by BIP type data.

The actual production allowed on each BIP type is indicated in the AVG and SLG columns, and is converted to run values and compared to MLB average in the REL PRD column. That figure is then adjusted for context, such as home park, team defense, luck, etc., in the ADJ PRD column. In the three right-most columns, his actual ERA, calculated component ERA based on actual production allowed, and “tru” ERA, which is adjusted for context, are all presented. For the purposes of this exercise, SH and SF are included as outs and HBP are excluded from the OBP calculation. Just for fun, I’ve added a few extra columns adjusting the data as if he played half of his games in Fenway Park, Wrigley Field, Dodger Stadium or AT&T Park.

First, a brief word about Fenway, Lester’s primary home park in 2014. Each year, I prepare my own park factors, based on granular batted-ball data. This season, as usual, Fenway had an extremely high fly ball park factor of 146.6, second only to Coors Field. This is largely due to the presence of the Green Monster, which has this nasty habit of turning routine fly balls into doubles. Fenway’s fly ball park factor to LF? 163.0, 2nd highest in the game. It’s fly ball park factor to LCF? 277.1, by far the highest. Its overall doubles park factor was 131, highest in the game. Its fly ball doubles park factor was 189, by far the highest in the game. You get the picture.

Against that backdrop, Lester ability to suppress fly ball damage in 2014 is quite remarkable. .227 AVG-.584 SLG, for an actual 65 REL PRD, adjusted slightly upward to 76 ADJ PRD for context, is quite an amazing accomplishment. Lester also allowed less than average damage on liners, with a 95 REL PRD, adjusted slightly downward to 90 ADJ PRD for context. He was actually quite unlucky on grounders last season, allowing .293 AVG-.320 SLG, for a hefty 147 REL PRD, adjusted downward to 115 ADJ PRD for context.

On all BIP, Lester had a REL PRD — an unadjusted contact score — of 93, adjusted slightly downward to 89 for context. Add back his exceptional K and BB totals, and his unadjusted and adjusted contact scores plunge to 79 and 75, respectively. His actual ERA of 2.46 was actually quite low due to sequencing; his context-adjusted “tru” ERA checks in at 2.82.

Moving 50% of his games into Fenway gives him a BOS PRD of 79 (the equivalent of a 2.97 ERA), and doing the same for Wrigley and Dodger Stadium give him comparable projections (78, 2.92 and 76, 2.86, respectively). All three are fly ball friendly; Fenway for previously discussed reasons, Wrigley thanks to its homer-friendly LCF, and Dodger Stadium largely thanks to a very reachable CF fence. AT&T Park is the second most pitcher-friendly park with regard to fly balls, with a 67.3 fly ball park factor. Lester would likely have the most success in San Francisco, though it can certainly be argued that the Red Sox need his ability to contain fly ball contact more than anyone.

That fly ball management skill, along with his reduced BB rate, was the primary driver taking him to a new level in 2014. His four-seam fastball and curveball pitch values shot upward this season, and those are the types of pitches that if located expertly can induce relatively high, can-of-corn fly ball contact.

When you physically draw a line halfway between the popup and line drive boundaries, splitting “high” from “low” fly balls, you notice a stark difference in offensive production between the two. Hitters batted just .094 AVG-.224 SLG on high fly balls, and .372 AVG-.960 SLG on low fly balls in 2014. 34.85% of all fly balls fit into the high group, 65.15% into the low. Well, 44.81% of Lester’s 2014 fly balls fit into the high group. This is a major increase from his 2012 (25.90%) and 2013 (32.51%) high fly ball rates. This seems to be directly tied to the uptick in effectiveness of his four-seamer and curve this season.

Overall, while Lester’s 2014 is an exceptional overall performance, it wasn’t in the league of Hernandez (2.27) or Kershaw (1.89), or even Corey Kluber (2.44). Guaranteeing in the vicinity of $150M to a pitcher who is not an outlier in almost every regard, like Hernandez or Kershaw, is very risky business. Heck, guaranteeing that kind of money even to those two is pretty scary; do you think Dodger fans were a bit nervous last April? Even elite pitchers are inherently significantly higher risks than elite hitters, largely due to much higher injury risk.

Kershaw’s contract extension runs him through his age 32 season, Hernandez’s runs thru age 33. Jon Lester won’t take the mound in 2015 until after his 31st birthday. If he does lock down that 7th year, that will carry him through his age-37 campaign. The team that signs him, at the very least, will be looking for him to stay healthy, let alone productive, for the duration.

In the history of our great game, a grand total of 35 pitchers have qualified for ERA title in each of the seven seasons from age 31 to 37. They appear below:

For each pitcher, the year in which they turned 31, their age 31-37 won-lost record, total IP, ERA and ERA+, as well as their career ERA+ are listed. You’ll notice that fully 10 of the 35 pitchers reached age 31 in just over a single decade, between 1967 and 1978. There’s another block of five pitchers turning 31 in the six years between 1994 and 2000, an outlier era in many ways. The World War I and II eras are pretty barren, as careers were often interrupted for war service.

In the current era, it has become increasingly rare for pitchers to qualify for ERA titles at advanced ages. Exactly five hurlers qualified for the ERA title at age 37 or higher this season; Bartolo Colon, Tim Hudson and A.J. Burnett in the NL, and Hiroki Kuroda and R.A. Dickey in the AL. Burnett became the 35th pitcher on the above list this season, and Jeremy Guthrie and Mark Buehrle have two more consecutive qualifying years to go to become the 36th and 37th.

Some of the pitchers on the above list — Greg Maddux, Warren Spahn and Steve Carlton, to name three — are all-time greats. Many others, like Don Sutton, Gaylord Perry and Early Wynn, are guys who peaked in the age 31-37 window and rode their career totals, rather than their peak ability, into the Hall of Fame. Others are named Murry Dickson.

Since 2001? Only Derek Lowe and A.J. Burnett have been added, only because they happened to be the lucky ones who stayed healthy. Guthrie and Buehrle fit the same mold. Many greater pitchers over the last decade either haven’t maintained their effectiveness or durability deep enough into their 30’s, or had a relatively significant career-interrupting injury at some point in the age 31-37 window. This is, among other things, what any team signing Jon Lester to a seven-year deal is up against.

Lester is one of the best pitchers in the game, and his arrow is pointed upward. His core skills are varied, and his decline phase should be productive. That said, he is a pitcher. Pitchers get hurt. Justin Verlander looked like a great deal a few years back, didn’t he? So did C.C. Sabathia, Masahiro Tanaka and Yu Darvish. They all got hurt, to varying extents, calling their present and future into greater question.

If it were me, I’d give Lester a very high AAV — around $25M — but only for five years, with a sixth-year option. Gun to my head, if I needed to guarantee the sixth year to get it done, I just might depending on the input of doctors, scouts, etc.. The seventh year is an absolute non-starter. Lines have to be drawn somewhere, and with pitchers they’re drawn a little bit closer to home.