Gerrit Cole, Stephen Strasburg, and the top end of the pitching market

The best two pitchers in the postseason, both former No. 1 overall draft picks, are now the best two pitchers on the open market, an unusual confluence of circumstances that are about to earn Gerrit Cole and Stephen Strasburg hundreds of millions of dollars.

Cole’s free agency was highly anticipated, especially after two post-trade years with the Astros that both maximized his ace potential and highlighted the development deficiencies of his former team, the Pirates, who got rid of their president, general manager and manager in the last six weeks.

That Strasburg is a free agent required action on his part. Already under contract with the world champion Nationals, Strasburg picked an opportune time to deliver on the promise of the most anticipated major league debut this century. Washington won all six of his October starts and Strasburg won World Series MVP, making it a rather easy decision to opt out of the four years and $100 million remaining on his existing deal.

Given recent contracts offered to ace pitchers, Strasburg will be able to surpass that in both length and average annual value. It pays to strike while the iron is hot.

Only 17 pitchers had a sub-3 ERA in at least 25 innings in a single postseason in the last decade. Three were this year (Cole, Strasburg, and Max Scherzer), so before 2019 it happened roughly three times every two postseasons. Cliff Lee in 2010 was the only one who was a pending free agent, and that winter he set a record for average annual value for a pitcher with his five-year, $120 million contract with the Phillies.

Justin Verlander had a 2.22 ERA in his four postseason starts in 2012, leading the Tigers to the World Series. While he wasn’t a free agent, the right-hander leveraged that performance the following spring into adding $140 million and five years to his existing deal, setting another AAV record in the process.

Verlander’s $28-million average annual value was surpassed in six multi-year contracts since, including three deals that were signed before the pitcher reached free agency. In addition, CC Sabathia ($30 million) and Clayton Kershaw ($28 million) each leveraged opt-out clauses in their own record deals to add one more guaranteed year to the back end.

The number to shoot for here is $34.42 million, the record average inked by Zack Greinke with the Diamondbacks before the 2016 season. The largest pitcher contract in total value is $217 million, signed by David Price with the Red Sox that same offseason.

You might be thinking paydays might be hard to come by since the last two winters have been relatively boring with spending lacking. The qualifying offer this offseason is $17.8 million, a one-year contract tender for the upper echelon of pending free agents, a tool that allows teams to get at least draft pick compensation for losing an elite player. That salary is determined by the average of the top 125 salaries of the current season, and for the first time in its existence the qualifying offer decreased from last year (down from $17.9 million). This is troubling, especially in a sport that keeps setting records for revenues.

But even in these relatively dark times for free agents — Dallas Keuchel and Craig Kimbrel saw their market crater so hard that they waited until midseason to sign, for instance — several elite players still got theirs. Bryce Harper signed for $330 million last winter and Manny Machado got $300 million. Mike Trout added $360 million to his deal and Nolan Arenado got a $260 million extension, and they weren’t even free agents.

There has also been money available — high-end money at that — for the cream of the crop among pitchers. Chris Sale parlayed a World Series win and six straight top-five Cy Young finishes into a five-year, $145 million extension from the Red Sox last March. That same month, Verlander inked a two-year, $66 million deal for his age-37 and 38 seasons with the Astros, an average annual value surpassed only by Greinke’s Arizona contract among pitchers.

The six pitchers who signed a contract with an average annual value of at least $30 million — I’m including Sabathia’s opt-out-leveraged one-year extension here — all had at least one Cy Young Award under their belt at the time they signed. Cole, if he doesn’t win the AL Cy Young this season, will finish no worse than second to Verlander, and at least had the type of season that is normally associated with a Cy Young Award, leading the league in ERA, ERA+, strikeouts, and FIP (Cole was second in wins and third in innings pitched).

Cole has the advantage of youth, heading into just his age-29 season in 2020, younger than all the pitchers with at least a $29 million AAV except for Kershaw.

Strasburg is two years older and had injury issues, averaging 145 innings from 2015-18, though he was generally excellent while on the mound. He bucked that trend in 2019, leading the National League in innings. Add in the postseason and Strasburg pitched 245⅓ innings, with Cole at 249 and Verlander 258⅓. Nobody pitched this much in a season since Corey Kluber in 2016 with the Indians and their run to Game 7 of the World Series.

It was the postseason that set Cole and Strasburg apart. They were No. 1 and 2 in innings in October, and both had sub-2.00 ERAs. Both struck out 47 batters, tied for the second-most in any single postseason. They combined to lose just one start between them.

Pitchers don’t often get a chance to parlay a month of postseason excellence in front of a captive national audience into immediate financial gain, but Gerrit Cole and Stephen Strasburg are poised to do just that.