Chris Sale Finally Cashes In

Chris Sale has long been one of the top pitchers in baseball — not only for pure performance but for bang for the buck, as he’s been working under one of the game’s most team-friendly contracts since 2013, which runs through this season. After an uneven season in which he reprised his 2017 dominance until shoulder inflammation limited his availability down the stretch, before capping a rocky October by closing out the World Series-clinching Game 5 against the Dodgers, the wiry southpaw has become the latest star to lock in big money early instead of testing the free agent market next winter or the one after that, following in the footsteps of Nolan Arenado, Mike Trout, and Paul Goldschmidt, all of whom have agreed to nine-figure extensions over the past four weeks. On Friday, Sale and the Red Sox agreed to a five-year, $145 million extension that will take him through 2024, his age-35 season. The deal reportedly includes some deferred money that lessens the impact on the Red Sox’s payroll for tax purposes, as well as an opt-out and a vesting option.

[Update: As some of the details regarding the structure of the contract were not reported until after this article’s original publication on Friday, I have revised this where necessary.]

Sale’s new deal succeeds the five-year, $32.5 million extension he signed in March 2013, his first year of arbitration eligibility. Via the two club options tacked onto that contract, he made $12.5 million in 2018 and will make $15 million in 2019, for a total of $59 million. That’s not exactly chump change, but it’s far below what the White Sox and Red Sox would have paid on the open market for the 34.7 WAR he’s delivered so far under that deal, the third-highest total among all pitchers. The two pitchers ahead of him, Clayton Kershaw and Max Scherzer, signed seven-year contracts worth $215 million and $210 million in 2014 and 2015, respectively. A similar payday for Sale has been long overdue, something the Red Sox had to know when they acquired him from the White Sox in a December 2016 blockbuster that cost the team infielder Yoan Moncada (who topped our prospect list the following spring and ranked second on that of Baseball America), pitcher Michael Kopech (21st on our list), outfielder Luis Basabe (now sixth on the White Sox list), and pitcher Victor Diaz.

Taking that initial extension, which Sale signed on the heels of a 192-inning age-23 season, wasn’t “the wrong” decision, necessarily. It was a move that guaranteed security for a pitcher whose mechanics and injury risk had already become the subject of much debate throughout the industry, and those concerns didn’t abate even after he signed his deal. Nonetheless, he’s avoided any disaster scenarios, throwing the fifth-highest total of innings in that 2013-18 span (1,196) while never dipping below 4.9 WAR even in the seasons in which he fell short of 200 frames.

In 2017, Sale’s first season with the Red Sox, he became the first AL pitcher to notch 300 strikeouts in a season since the turn of the millennium (308, all told) while leading the majors in innings (214.1), FIP (2.45), and WAR (7.5), though he faded somewhat down the stretch and finished second in the AL Cy Young voting behind Corey Kluber, whose 2.25 ERA (and 8.2 bWAR) carried the day. It was the sixth consecutive season in which Sale had earned All-Star honors and received Cy Young consideration.

Through the first four months of last season, Sale appeared to be on track to finally win the award, starting the All-Star Game for the AL and carrying a 2.04 ERA and 2.08 FIP into late July before missing two starts with shoulder inflammation. Upon returning, Sale threw five innings of one-hit shutout ball against the hapless Orioles, striking out 12 — his 11th double-digit game of the year — on just 68 pitches. But he went back on the DL before he could start again, and the Red Sox, who were running away with the AL East at the time, chose to play it safe. Sale pitched just 12 innings in four September appearances, and finished with 158 innings, four short of qualifying for the ERA title; his 2.11 mark would have ranked second in the league and his 1.98 FIP first, and even with the limited work, his 6.2 WAR ranked second. The shortfall of innings cost him the Cy Young, as Blake Snell and his 21 wins and 1.89 ERA in 180.2 innings brought home the hardware.

The Red Sox’s cautious handling of Sale extended into the postseason, as he totaled just 13.1 innings in three starts, with only his Division Series Game 1 turn against the Yankees lasting longer than four innings. He made two one-inning relief appearances, one in Game 4 of that series and the other in the ninth inning of Game 5, where he struck out the side to seal the Red Sox’s fourth championship in the past 15 seasons.

Repeatedly, Sale and the Red Sox have expressed confidence in the pitcher’s condition. In late August, Sale said that his shoulder felt “like Paul Bunyan’s ox” and in September he said he had no plans to fuss over his mechanics because his shoulder was structurally sound. “There was never any major issue with my shoulder,” he said. “This wasn’t something that happened on a single pitch or a mechanical issue or anything.” As of January, he felt “normal again. Being able to throw free and easy and feel loose … obviously is a nice feeling.”

Apparently the Red Sox are still confident enough in the condition of Sale’s shoulder to commit to him for five years beyond this one, at a salary near the top of the scale for pitchers. While initial reports regarding the contract contained no word of the various bells and whistles beyond some unspecified amount of deferred money, the structure has since been clarified by multiple sources. Sale will be paid $30 million per year for the first three seasons (2020-22), after which he can opt out; if he does not, he will receive $27.5 million per year for 2023-24. His annual salaries can increase by up to $2 million per year based upon his finishes in the Cy Young voting, and a $20 million option for 2025 will vest if he finishes in top 10 in the 2024 Cy Young vote and does not finish the season on the injured list. The deferrals lower the average annual value of the deal to $26.5 million for tax purposes. Based upon that figure, Sale’s AAV trails only those of Justin Verlander ($33 million, for a 2020-21 extension announced hours after Sale’s) Zack Greinke ($32.5 million after deferrals), Kershaw’s latest extension and teammate David Price (both $31 million), Kershaw’s previous extension, which he opted out of after the 2018 season ($30.71 million), Scherzer ($30 million), Jon Lester ($25.83 million), and Verlander again ($25.71 million via his current deal). That said, according to Craig Edwards’ recent inflation-adjusted look at the largest contracts in history, Sale’s deal would actually rank eighth behind the deals of Kevin Brown, Kershaw and CC Sabathia (both pre-opt out), Scherzer, Verlander, Mike Hampton, and Felix Hernandez.

As with Arenado and Goldschmidt, running Sale’s numbers through our contract estimation tool using even conservative parameters ($8.0 million per WAR and just 3% average annual inflation, as opposed to $9 million or more, and 5%) yields an eye-opening valuation:

Where Goldschmidt’s estimate using the same parameters came in 20% higher than his actual deal, the estimate for Sale is around 40% higher. But unlike in the case of Goldschmidt, where applying estimates of $9 million per win and 5% inflation to a ZiPS projection — which is generally more conservative than this model — provided by Dan Szymborski produced a figure that more closely resembled his actual contract, sticking with $8 million per win and 3% inflation for Sale in this model overshoots the mark by even more:

Even while projecting relatively low innings totals, ZiPS sees Sale as half a win more valuable over that timespan than our contract estimation tool does. Indeed, Szymborski says that only Luis Severino and German Marquez (!) project to produce more WAR over the remainder of their careers. Dan’s computer is so sweet on the southpaw that it’s probably sending heart-shaped boxes of chocolate to his locker as I type. Remember, for both of Sale’s estimates I’ve lopped off his 2019 performance, in which he projects to deliver something around $47-$49 million of value while being paid just $15 million.

Based upon that $145 million figure, either the Red Sox are significantly underpaying Sale or expecting a lot less, performance-wise, than the projection systems (for what it’s worth, Baseball Prospectus’ PECOTA system projects Sale for 22.1 WARP over the 2020-24 period). Which doesn’t seem entirely unreasonable, as they’re the ones with access to his medical file, and the risk of a career-altering injury for a pitcher is ever-present. Working backwards with the ZiPS projection and our conservative $8 million and 3% parameters, a five-year forecast of 17.0 WAR produces a valuation of $147.7 million. At $9 million per win and 5% inflation, 14.0 WAR produces a valuation of $144.2 million.

Regardless of the projections, the contract adds one more hefty salary to the Red Sox payroll, which for tax purposes already has $105.5 million worth of commitments for 2020 and $106.0 million for 2021, primarily via the deals of Price (an AAV of $31 million), J.D. Martinez ($22 million), Nathan Eovaldi ($17 million), Dustin Pedroia ($13.75 million), and Christian Vazquez ($4.517 million). That’s before any extension or arbitration raise for Mookie Betts (who has just one more year of club control), and without counting the pending free agencies of Rick Porcello or Xander Bogaerts, though it’s worth noting that Martinez can opt out after this season. If the Red Sox, who already project to be about $31.6 million over this year’s Competitive Balance Tax threshold — so far over that they incur a surtax — are going to avoid progressively larger tax bills, they’ll have to make some tough choices in the near future, and find some lower-cost players to fill out their roster. Keeping Sale, alongside Price and Eovaldi, almost certainly means letting Porcello walk, and Bogaerts, too, because as a Scott Boras client, the likelihood of his agreeing to a team-friendly extension appears to be slim.

As for Sale, he doesn’t have to remain in perennial Cy Young contention to make this deal worthwhile, but the fact that he’s been able to do so is what’s made him so attractive a player in the first place. He’s earned his big payday, and while he might have received an even bigger one by going on the market, the inherent risks of pitching make this a sensible move for him as well.