Gerrit Cole Signs 9-Year Deal

December 2019. Yankee Stadium. A press conference podium, not a pitcher's mound -- but the energy in that room felt like Game 7. Gerrit Cole sat down in front of the microphones, pulled on a pinstriped jersey, and the New York Yankees finally had their ace. Nine years. $324 million. The richest contract ever handed to a pitcher in baseball history. And for a kid from Orange County who'd grown up idolizing Jeter and Mo, it was eleven years in the making.

The Drought

Here's what you need to understand about the 2019 Yankees -- they were GOOD. 103 wins. A lineup with Judge, Stanton, DJ LeMahieu, Gleyber Torres. A bullpen that could shut down anyone from the sixth inning on. They had everything except the one thing October demands: a frontline starter who can walk into a hostile ballpark, take the ball in a do-or-die game, and make the other team look helpless.

Nobody in the rotation fit that description since CC Sabathia's peak years. They'd been patching it with mid-rotation arms, hoping the offense would carry them. It carried them all the way to the 2019 ALCS -- where they ran into Houston and got bounced in six games.

The guy who bounced them? Gerrit Cole.

The Kid Who Said No

Full-circle stuff here is almost too perfect. Cole grew up in Newport Beach, California, rooting for the Yankees. There's a famous photo of him as a kid wearing a Yankees World Series shirt -- not some staged PR thing, but an actual childhood snapshot that got passed around the internet when the signing happened. (The man literally grew up in the fandom.)

The Yankees drafted Cole 28th overall in 2008 out of Orange Lutheran High School. He turned them down. Went to UCLA instead, bet on himself getting a bigger payday three years later, and he was right -- Pittsburgh took him first overall in 2011 with an $8 million bonus. Smart move. Painful for the Bronx.

Cole spent five years in Pittsburgh, had one truly dominant season in 2015 (19-8, 2.60 ERA), then got traded to Houston in January 2018 in a deal that sent Austin Meadows, Tyler Glasnow, and Shane Baz the other way. And that's when everything changed.

Houston Made Him a Monster

The Astros' pitching infrastructure -- the spin rate analytics, the pitch design lab, the whole operation -- unlocked Cole. He went from a good starter to a freakin' force of nature. In 2018 he struck out 276 batters and posted a 2.88 ERA. Then in 2019 he went completely supernova: 20-5, a 2.50 ERA, and 326 strikeouts in 212.1 innings. That K total led baseball by a laughable margin. His 13.82 K/9 rate ranked among the highest single-season marks in the modern era.

He finished second in AL Cy Young voting behind teammate Justin Verlander -- which tells you how absurd the 2019 Astros rotation was. In almost any other year, Cole's season wins that award unanimously.

Then came October. Cole started Game 1 of the ALCS against the Yankees, and he was dominant. The Yankees' front office watched from the opposing dugout as the pitcher they'd drafted eleven years earlier carved their lineup up on the biggest stage. Two months later, they made sure it'd never happen again.

The Boras Masterclass

Scott Boras -- Cole's agent and the best negotiator player representation has ever seen -- ran a bidding war that business schools should teach for decades. The Angels made a serious push (Cole grew up in their backyard). The Dodgers sniffed around. But Boras had an ace up his sleeve beyond just Cole.

On December 11, 2019, Boras's other star client, Stephen Strasburg, signed a 7-year, $245 million deal with Washington -- setting a brand-new pitcher record. Days later, Cole's deal shattered it. Nine years, $324 million. $36 million a year. Two years longer and $79 million richer than Strasburg's deal, which had held the record for approximately one week. (Boras set the ceiling, then immediately blew through it with his next client. The man's a genius at this.)

When I was a kid, I used to draw up these dream scenarios: playing for the Yankees in the World Series. When you're 8 years old, you don't know who the other teams are. You just know the Yankees are on top.

That's not a rehearsed PR line. That's a dude who spent his childhood in a Yankees t-shirt finally getting to put on the real thing. Brian Cashman stood at the same podium and didn't mince words -- he called Cole the best pitcher in baseball and said the Yankees intended to use him like it.

The Aftermath

Cole's Yankees career hasn't been a straight line. The COVID-shortened 2020 season gave him 12 starts (7-3, 2.84 ERA) and immediate credibility as the ace. The 2021 sticky-stuff controversy got messy -- when asked directly about Spider Tack, Cole gave a non-answer that everyone read as an admission. His spin rates dropped after MLB started checking. (Not a great look.)

In 2022, he was solid but not dominant -- 13-8, 3.50 ERA -- and the New York press started doing what the New York press does with a $324 million arm that isn't putting up historically dominant numbers.

Then came 2023. Cole went 15-4 with a 2.63 ERA, 222 strikeouts in 209 innings, and won the American League Cy Young Award -- the first Yankee to win one since Ron Guidry in 1978. Forty-five years. That's how long the drought lasted, and Cole ended it. Whatever questions hung over the first few years of his deal, the 2023 season answered them.

A UCL injury wiped out a huge chunk of his 2024 season -- Cole made just 8 starts before landing on the IL, then gutted his way back for 9 more down the stretch (17 total). But the investment had already paid for itself. The Yankees got their ace, and the kid from Newport Beach got his dream.

Frequently Asked Questions

How much did Gerrit Cole sign for with the Yankees?

Cole signed a 9-year, $324 million contract in December 2019 -- the largest deal ever given to a pitcher in Major League Baseball history at the time. The deal averaged $36 million per year, also the highest annual salary any pitcher had ever received.

Was Gerrit Cole drafted by the Yankees?

Yes. The Yankees selected Cole 28th overall in the 2008 MLB Draft out of Orange Lutheran High School in Orange, California. Cole declined to sign and attended UCLA instead. He went first overall to the Pittsburgh Pirates in 2011, spent time in Pittsburgh and Houston, and finally signed with New York as a free agent in December 2019 -- more than eleven years after the Yankees first drafted him.

Has Gerrit Cole won a Cy Young Award with the Yankees?

Yes. Cole won the 2023 American League Cy Young Award, going 15-4 with a 2.63 ERA and 222 strikeouts in 209 innings. He became the first Yankees pitcher to win the Cy Young since Ron Guidry in 1978.