No pitcher has ever been in quite the position that Gerrit Cole is. The 29-year-old righty with the triple-digit heat has yet to win or even reach the World Series, but his Astros are still favored to beat the Yankees in the ALCS, and he’ll have more than a little influence over that outcome, beginning with Tuesday afternoon’s Game 3 start. Meanwhile, though he has yet to win the AL Cy Young award, after a season in which his 326 strikeouts, 2.50 ERA, 2.64 FIP and 7.4 fWAR all led the the American league, Cole is at the very least a co-favorite alongside teammate Justin Verlander. Before we know the answer to whether he’ll claim the latter piece of hardware, he will reach free agency, putting him in position to ink the largest deal ever for a pitcher.

That could make for an impressive trifecta, and one whose only precedent comes with an asterisk. In December 1974, at the end of a season in which he helped the A’s to their third straight championship and claimed the AL Cy Young award on the basis of a 25-12 won-loss record with a 2.49 ERA, Catfish Hunter had his two-year, $200,000 contract with Oakland voided by a three-person arbitration panel after owner Charlie Finley failed to make deferred annuity payments in a timely fashion as stipulated by the deal. Every team except the Giants attempted to woo the sudden free agent, who on December 31, signed a record-setting five-year, $3.2 million deal with the Yankees. A year later, that same panel, comprised of MLB Player Relations Committee chief negotiator John Gaherin, MLBPA Executive Director Marvin Miller, and impartial chairman Peter Seitz, would rule in favor of pitchers Andy Messersmith and Dave McNally, nullifying the reserve clause and creating free agency as we know it.

Since then, only four hurlers have had their Cy Young awards line up with free agency:

Additionally, Dennis Eckersley bypassed free agency by agreeing to a two-year, $7.8 million extension in August 1992, months before he would win his Cy Young award on the strength of a 1.91 ERA and AL-high 51 saves.

None of those players had their award and walk year line up with a trip to the World Series. So far, neither has Cole, but he’s in a position to do something about that. Already this October, he tied an AL postseason record by striking out 15 Rays over seven and two-thirds shutout innings in Game 2 of the Division Series; only the Padres’ Kevin Brown (16 in Game 1 of the 1998 Division Series against the Astros) and the Cardinals’ Bob Gibson (17 in Game 1 of the 1968 World Series against the Tigers) notched more in a single game. Meanwhile, after striking out 10 Rays in eight innings in Game 5 while allowing just two hits, two walks and one run, Cole became the 10th pitcher to reach double digits in strikeouts in consecutive postseason starts. He can become the fourth to make it three in a row after Gibson (Game 7 of the 1967 World Series against the Red Sox, plus Games 1 and 4 in ’68), the Rangers’ Cliff Lee (Games 1 and 5 of the 2010 ALDS against the Rays, and Game 3 of the ALCS against the Yankees), and the Tigers’ Verlander (Games 2 and 5 of the 2012 ALDS against the A’s, and Game 3 of the ALCS against the Yankees). He’s now at 11 straight games with at least 10 strikeouts overall, including his final nine of the regular season dating back to August 7. You could power a city with the wind his swings and misses has created.

After a season in which he set a record for an ERA qualifier by striking out 39.9% of all batters faced — yes, that’s somewhat a product of the environment, as his 176 K%+ ranks a more modest 122nd out of 8783 qualifying seasons since 1901 — Cole has punched out 46.3% of the batters he’s faced in October, that while lowering his walk rate from 5.9% to 5.6%; his K-BB% is a ludicrous 40.7%, up from 34.0% in the regular season. Meanwhile, batters are hitting just .118/.167/.196 against him, with Kevin Kiermaier‘s Game 1 double and Eric Sogard’s Game 5 homer the only extra-base hits.

Cole hasn’t changed a whole lot from what he was doing in the regular season. His four-seam fastball has a bit of extra zip (97.5 mph according to Baseball Savant, compared to 97.2 mph), and he’s using it slightly more often at the expense of his slider (see below). He’s getting slightly more swinging strikes overall (17.3%, up from 16.5%) thanks to his breaking stuff:

Cole’s Pitches, Regular vs. Postseason Split FF CH SL CU Reg season usage 54.0% 7.4% 23.2% 15.4% Postseason usage 57.3% 6.2% 20.4% 16.0% Reg Swstr% 17.0% 18.4% 20.1% 8.5% Post Swstr% 14.7% 14.3% 22.9% 20.6% SOURCE: Baseball Savant

A closer look shows that he’s increased his usage of the curve against lefties relative to the regular season:

Cole’s Pitches by Batter Handedness Split FF CH SL CU LHB Reg season 55.9% 10.9% 15.5% 17.6% LHB Postseason 57.3% 12.0% 9.4% 27.4% RHB Reg season 51.6% 3.5% 31.8% 13.0% RHB Postseason 57.4% 0.0% 34.3% 8.3%

With that spike in curveball usage, Cole has nearly quadrupled his swinging strike rate on the pitch to lefties, from 7.3% in the regular season to 28% in the postseason; five times, Rays lefties went down swinging against the pitch. Here’s Austin Meadows in the first inning of Game 2:

And here’s Kiermaier in the eighth inning of Game 5, probably very, very sorry about the aforementioned double:

If there’s good news for the Yankees, it’s that they don’t have a huge left-handed presence in their lineup, with Brett Gardner and Didi Gregorius the only lefty starters, so they’ll probably see fewer of those curves. The bad news is that Cole’s slider is a more effective offering, with batters managing a mere .224 wOBA against the pitch compared to .260 for the curve, and as I pointed out in my ALCS preview, the Yankees have had less success against sliders (.300 wOBA, sixth in the majors) than curves (.321, fourth in the majors) this year. The fact that batters haven’t been any more effective against Cole’s fastballs (.259 wOBA) or changeups (.268) is a major reason why he posted the majors’ lowest wOBA allowed the third time through the order (.231, four points better than Verlander and seven points better than teammate Zack Greinke as well).

Waiting Cole out, the way the Joe Torre-era Yankees used to do with Red Sox ace Pedro Martinez, by building up his pitch count, may not be the most effective strategy. Sixteen of the pitcher’s 66 runs allowed this year (24.2%) came in the first inning; that’s 4.36 runs per nine. He walked 11.7% of batters faced in the first, about double his overall rate, struck out “only” 33.6% of them, and allowed seven first-inning homers (1.9 per nine). His wOBA allowed in the first frame was .298, 38th out of the 120 pitchers with at least 80 batters faced in that context. At that, his wOBAs the first and second times through the order (.249 and .257, respectively) are higher than the third time through. Getting him early is probably the pinstripes’ best chance.

Having split their first two games in Houston — barely, given that it took 11 innings to outlast the Yankees in Game 2 — the Astros are hardly assured of winning this series, let alone the World Series, though our playoff odds rate their chances at 44.4%. As for the Cy Young award, Cole has the edge in the aforementioned categories, but Verlander had the higher bWAR (7.8) and xWAR (8.6 to 8.2); the latter is Craig Edwards’ xwOBA-based version of the stat, which is driven by the quality of contact yielded while attempting to strip out the effects of ballpark, defense, and luck. That may be a bit esoteric for the tastes of most BBWAA voters, but it’s a reminder that not every stat favors Cole:

AL Cy Young Race: Cole vs. Verlander Name W-L IP K K% BB% K-BB% HR/9 ERA FIP fWAR bWAR xWAR Gerrit Cole 20-5 212.1 326 39.9% 5.9% 34.0% 1.23 2.50 2.64 7.4 6.9 8.6 Justin Verlander 21-6 223.0 300 35.4% 5.0% 30.5% 1.45 2.58 3.27 6.4 7.8 8.2 Blue = AL leader. Yellow = leader of this pair.

Verlander does have some additional considerations that may carry a bit of weight with some voters. He recorded his third no-hitter and 3,000th career strikeout this year. He’s also been a very close second in the voting three times, including in both 2016 and ’18, and is perceived as having gotten a raw deal particularly in the former year, when he had 14 first-place votes to winner Rick Porcello’s eight. If we call the race a coin toss, that lowers Cole’s odds of the aforementioned double to 22.2%; if it’s 60-40 in his favor, that’s a 26.6% chance.

What’s in less doubt than either or both of those victories is the likelihood of Cole netting the largest contract of any pitcher by some measure. Dan Szymborski’s preliminary ZiPS projected contract puts him at seven years and $264 million, which would obliterate the seven-year deals of David Price ($217 million), Clayton Kershaw ($215 million), and Max Scherzer ($210 million) by such a wide margin that it seems implausible. If Cole were to get seven years with an average annual value just ahead of Verlander ($33 million) and Greinke ($32.5 million) — call it $33.5 million — that’s $234.5 million. He may not find a team willing to quite go that high, but one can see that there’s still plenty of wiggle room for him to claim the largest contract. And given his combination of age (he just turned 29 on September 8), health (he’s reached 200 innings in four of his past five seasons, and the 2016 elbow trouble (a triceps strain, elbow inflammation, and impingement) that limited him to 116 innings hasn’t been an issue since), performance (his 13.4 fWAR over the past two seasons trails only Jacob deGrom’s 16.0 and Scherzer’s 14.0), and timing, there’s little reason he won’t get there, even in this rather frosty free agent environment. Regarding his timing, a quick glance at the league’s fWAR leaderboard over the past three seasons (where Cole’s 16.8 ranks fifth) shows that he and the sixth-ranked Strasburg (14.0) are the only pitchers from the top 20 reaching free agency this year, with ninth-ranked Corey Kluber (13.3), 12th-ranked Trevor Bauer (11.9), and 13th ranked James Paxton (11.6) on track to do so after 2020, albeit with less flattering multiyear trends. This is the rare chance for a team to land a bona fide ace.

It’s an enviable position to be in, for sure. While some of the things that have to happen for Cole to hit this particular trifecta are beyond his control, by now there should be very little doubt that he’s capable of maximizing his chances for the ultimate jackpot.