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25 Smartest Moves of the Past 25 Years: Yankees sign Gerrit Cole

The club signed the best available pitcher, and it’s worked out wonderfully. What a concept.

MLB: New York Yankees-Gerrit Cole Press Conference Danielle Parhizkaran-USA TODAY Sports

My favorite Yankee transactions have been the ones where the team just decided “hey, this guy is really really good. Let’s give him more money than anyone else.” It works especially well with starting pitching, like with the Mike Mussina deal or CC Sabathia or Masahiro Tanaka. But perhaps no such deal has worked out quite as well as Gerrit Cole.

After watching Cole carve up the AL through the 2019 season, the Yankees had the CBT space and need for an ace, and for the early stages of the winter it sure felt like Brian Cashman would not be denied. On a late Tuesday night during the Winter Meetings, Cole agreed.

Signing Details: Gerrit Cole signs a 9-year, $324 million contract with a fifth-year opt out. The Yankees can add a 1/$36 million extension to override the opt-out decision.

Transaction Date: December 10, 2019

NYY stats: 42 games, 254.1 IP, 3.11 ERA, 138 ERA+, 3.20 FIP, 33.2% K%, 5.7% BB%, 6.7 fWAR

Cole was always a favorite of the Yankee front office. They drafted him out of high school in 2008, knowing that he was going to end up at UCLA. They tried to trade for him in 2017 when it was clear he wasn’t going to unlock his full potential as a Pirate, but didn’t want to part with Miguel Andújar, Clint Frazier or Chance Adams. Instead, they saw him go to the Astros, where in 2019 he had, at least by K-BB%, the single most dominant season by any starter, ever.

But a funny thing happened in that 2019 World Series. Gerrit Cole was ready, willing and able to work out of the bullpen in the decisive Game 7, but AJ Hinch just left him down there. Not to relitigate a World Series my team didn’t play in, but I still feel the best move would have been to go to Cole after Will Smith gave up a two-run shot to Howie Kendrick. The game was 3-2 at that point, you’re only down by a run, it seems prudent to bring in the most dominant pitcher in the game, keep it close, and give yourself a chance to get a run. Instead, the Astros went with a conventional approach, the Nats added a trio of insurance runs, and the Series was over.

I don’t know if that decision was the straw that broke the camel’s back for Cole, but he seemed to cut ties with the Astros almost immediately, even wearing his agent’s hat over his club’s in the postgame presser:

The White Whale of the 2019 offseason, it eventually came down to a trio of clubs, with the Yankees and Angels competing offer-for-offer, and the Dodgers a distant third. Brian Cashman, who is often criticized for having a fairly inflexible negotiating style, ended up securing the deal both with a ninth guaranteed season, and the tenth-year option as a hedge against an opt-out. The Yankees had their ace, and we, well, we were excited:

It’s one of the great frustrations of baseball in a COVID-19 world that Cole’s first season, at age 29, was so abbreviated. He got his first of what will be several Opening Day starts, but it didn’t come until July 23, 2020, where he threw five innings of one-run ball against the Nationals.

You all know about Cole’s on-field performance. He had a strong campaign in 2020, the rock in an extremely chaotic season, and then was even better last year, finishing first or second in the AL in virtually every statistical category. More important than recounting his past two years, I’d like to talk about what the future holds and how confident I am in Cole continuing his greatness.

The last year, maybe the last two, of a mega deal are always going to be write-offs. You build up surplus value on the front end of the contract, and then it makes stomaching the back end easier. The middle of the contract is where we really find out whether a signing was worth it or not, and Cole’s cerebral approach to pitching is why I think it’s going to. He’s not just a physical freak — the dude is 6-foot-4 with a wild wingspan and throws the ball at your neck at 101 mph — he’s also among the smartest, and most curious, athletes in the game today.

This is just one example. For most of his time after leaving the Pirates, Cole was a three-pitch pitcher, working east-west with his slider and north-south with his curve, all backed by one of the game’s best fastballs. After getting a full year to work with Matt Blake, Cole began using his changeup more, and more, until now he’s a real four-pitch guy. He’s not just using the change, it’s a good change, with a .225 wOBA against in 2021, and playing up his fastball, which saw wOBA against drop more than 100 points once the changeup was brought into regular use.

This kind of adjustment, from a guy who’s guaranteed $324 million and is already one of the two or three best pitchers in the game, is why I’m so confident in Cole going forward. He’s not the kind of player to be content with his current production and skills, constantly trying new things and looking to improve. As a player ages, that kind of attitude is going to be what allows him to compensate for likely drops in velocity or similar depreciations due to age.

Perhaps the greatest joy for Yankee fans over the past two seasons has been getting to watch Cole start, and its a testament to what can be accomplished when the Yankees leverage their financial might. Intelligence is knowing how to use all your resources to reach your goals, and while the Yankees haven’t quite reached their World Series title with this core, they’re a lot closer with Gerrit freakin’ Cole than they are without.