50 Most Notable Yankees Free Agent Signings in 50 Years: Gerrit Cole

New York Yankees pitcher Gerrit Cole, second from right, holds the sign he was photographed holding at the 2001 World Series as a kid as he poses for photos with, from left, Scott Boras, Hal Steinbrenner, and his wife Amy during a press conference at Legends Club at Yankee Stadium in New York on Dec. 18, 2019. | Danielle Parhizkaran, Danielle Parhizkaran / USA TODAY NETWORK via Imagn Images

I have my complaints about the Hal Steinbrenner-Brian Cashman administration, with one of the big ones being that it’s not always clear where Cashman’s decision authority stops and Hal’s starts. The one thing you can never take away from the duo though is that when they want a guy, really want him, they pull out all the stops to get him. Following a devastating loss in the 2019 ALCS, the Yankees needed a true ace to compete with the Red Sox and Astros, the two teams that had bounced them from the postseason in the previous three years.

Meanwhile, Gerrit Cole was putting up numbers that made him look like a hydrogen bomb going up against coughing babies with Louisville Sluggers. As the lead photo to this post commemorates, Cole also famously grew up a Yankee fan, and his signing was something of a homecoming — one that bar a devastating Tommy John surgery, has paid off in spades.

Gerrit Cole
Signing Date: December 16, 2019
Contract: 9 years, $324 million

Cole’s kind of always been the golden boy. His senior year of high school at Orange Lutheran High he sat 96 mph, striking out 121 batters in 75 innings. Of course the Yankees actually drafted him long before signing him in 2019, 28th overall in the 2008 draft. The club offered an overslot $4 million bonus, but the righty stuck to his commitment with UCLA. Three years later, Cole went 1-1 and signed with the Pirates for $8 million.

But then, he did go to the soon-to-be-resurgent Pirates, a franchise that was being widely celebrated at the time for building strong pitching, backed by Ray Searage’s encouraged use of sinkers and two-seam fastballs. Cole was never bad with Pittsburgh, putting up a 5.1-fWAR season in 2015 and finishing fourth in NL Cy Young Award voting, but it always felt that he had another gear to reach. Perhaps a philosophical misalignment—with Cole rivaled perhaps only by Justin Verlander in this era of taking a “screw you, hit this” approach to his repertoire—kept Gerrit from being the ace he would later emerge as.

Regrettably we got to see that pairing for two years, as the Houston Astros added Cole to a very, very dangerous rotation ahead of the 2018 season. That philosophical match was there, as was some sticky stuff, and the big righty put up 13.4 fWAR in two years with Houston — fanning 40 percent of batters he faced in a 326-K 2019!! If only he didn’t dogwalk the Yankees while doing so, we’d all probably remember this fondly.

What I do remember fondly is the famous Boras Corp. hat Cole sported after going unused in a World Series Game 7 loss, signaling that the game’s best pitcher was going to be available to the highest bid. The Yankees, with their Baby Bomber core already starting to show some cracks — love you forever, Gary Sánchez — were in need of A Guy to pair along with Aaron Judge.

Of course having one of the most dominant pitching seasons since Peak Pedro right before becoming a free agent meant there were many suitors, with the Angels, Padres, Phillies, and Astros all expected to be significant competitors, and the Yankees not even considered favorites. The club did catch a break when the Angels bit on Anthony Rendon just before Cole signed, with the former Nationals’ third baseman going to Orange County, and that tale is a much less happy one.

In the end, the Yankees pulled out all the stops on this one. The organization showed up at the right-hander’s door with an entourage that included his childhood hero Andy Pettitte, who spoke about the uniqueness of success in pinstripes. New pitching coach Matt Blake was also part of the delegation, detailing his plans to revamp Yankee pitching development, and appealing to the often-professorial attitude Cole takes to his craft.

The $324 million, nearly double what the Yankees landed CC Sabathia for just over a decade earlier, certainly helped as well. Gerrit Cole was going to be the Opening Day starter for the New York Yankees, in an ironic echo from what might have happened 10 or so years before.

That first start was a strange one, coming in July in an empty stadium as baseball grappled with continuity in the time of COVID-19. Perhaps we could see that first start as an omen of sorts, with the time since seeing Cole win a Cy Young, start a World Series game, and twirl one of the more impressive regular season outings in recent Yankee history on July 10, 2021:

Yet just like all of Aaron Judge’s lofty, indeed historic, accomplishments, everything that Cole has done as a Yankee has ended in a bit of disappointment. In the 2021 AL Wild Card Game, the win-or-go-home playoff outing that you expressly sign a player like Cole for, he gave up a pair of home runs early to put the Yankees down 3-0 and was out after two innings (due in part to a nagging hamstring). The Yankees couldn’t recover and went home.

The team had their backs to the wall in Game 5 of the 2024 World Series, this time in the Bronx, once again the exact type of scenario you imagine when you ink an ace to a deal commiserate with his talent. Gerrit Cole played a pivotal role in that nightmare fifth inning, not agreeing with Anthony Rizzo on who should cover first base, and unable to re-establish control over the frame after other errors in the way that we have seen him do so before.

And then came that bad news last spring, just about exactly a year ago. Elbow discomfort, MRI, Tommy John surgery, and a lost year. We don’t know at press time when Cole will be back—probably mid-to-late May by the updates the club has provided—but just like that your nominal ace is 35, hasn’t pitched in anger since that World Series game, and hasn’t had a season without elbow trouble since 2023.

If nothing else, Gerrit Cole is a marked case of Get Caught Trying. Nothing is guaranteed, no one player means that you’re going to win the last game of the season. No active pitcher has a higher career WAR without a World Series ring than Gerrit. Even one of the last, great, 200+ inning workhorses can be felled by a ligament about the size of a Q-tip. Man proposes and baseball disposes, but put it all together and try. The biggest criticism of the post-dynasty Yankees has been that they’ve refused to push it all in at once, but signing Gerrit Cole was probably the closest we’ve gotten to it, and there’s a reason there’s a No. 45 jersey in my closet.


See more of the “50 Most Notable Yankees Free Agent Signings in 50 Years” series here.



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