A Twist Of Fate: Cy Young Winner Gerrit Cole’s Serendipitous Road To The New York Yankees

Photo Credit: Mark Hanson

BY LAURA SCHREFFLER
PHOTOGRAPHY MARK HANSON
STYLING KARINA BOYLAN
GROOMING JUANITA LOPEZ
SHOT ON LOCATION AT MONTAGE LAGUNA BEACH

Fate, by definition, is the development of events beyond a person’s control; a predetermined path that seems dictated by circumstance but is actually dictated by unforeseen forces. There is still choice, but with it, awareness that you’ll still arrive at the very same place. In Gerrit Cole’s case, this is particularly true: it seems predetermined that the Major League Baseball pitcher was always destined to wear New York Yankees pinstripes.

It didn’t seem likely though. Cole is a born and raised California boy, and one who still lives there occasionally in the off-season to boot. But one defining characteristic I discover during our chat is a fierce loyalty and love of family — and because the Yankees were his father’s team, they inevitably became his team, too. Which is why Cole, aged 11, found himself at the 2001 World Series holding up a sign that read, “Yankee fan today, tomorrow, and forever.”

It was this very sign, with crinkled edges, peeling letters, and all, that reemerged at Cole’s introductory press conference with his favored team, just after signing a historic, nine-year, $324 million contract — the largest given to a pitcher at the time — with the Yankees on December 18, 2019. His parents had kept it safe for almost 20 years, as if they knew where he’d one day land.
“We all have dreams, but we just chase them irrationally when we’re [young]. It’s surreal to think back on it now,” he admits, before recalling seeing his lifelong commitment to the team make its way to the podium in all of its battered glory. “I had a feeling that [my parents] had kept it, but I hadn’t seen it. I didn’t know what shape it was in — it was pretty beaten up — but my parents brought it and didn’t tell me. I was surprised, and thought Wow, what a full circle moment; what a lucky guy I am,” Cole recalls.

The circle is even bigger than you might realize. After playing ball at Orange Lutheran High School in Orange, California (gaining immediate recognition while pitching for the varsity team during his junior year, with a fastball that reached 94 miles per hour), he was selected by the Yankees in the first round of the 2008 MLB draft (who were reportedly planning on offering him a $4 million signing bonus, which was above the recommended amount at the time) but he decided not to sign with them. Instead, he opted for education first, and enrolled at the University of California, Los Angeles on a baseball scholarship, where he majored in political science and played ball for the UCLA Bruins.

Mind-boggling, no? But Cole had a practical, highly logical reason, and one that speaks to his character completely (because what 18-year-old kid would choose education over an MLB contract?). “My folks, and all of us as a family, put a lot of priority on school,” he explains. “This industry is hard — it’s hard to get into the Major Leagues — and there’s never a guarantee that you’ll make a career of it past two or three years; the odds aren’t in your favor. Some players are on a seven- or eight-year journey and end up not making it. What’s your fallback at that point? Why put all your chips in that one basket? I was young, and it was important to me to make sure that I could develop as a baseball player and lay a foundation for a life after baseball. It was the most prudent route: we tried to figure out how to put a value on starting my career three years early, and it just didn’t seem like the best fit for me. I was able to knock out three quarters of my education during that time. Plus, most importantly, I met my wife [of seven years, Amy] at UCLA.”

Photo Credit: Mark Hanson

I wonder if he thinks about how differently his life would have played out should he have signed with the Yankees in 2008. Although he admits it has crossed his mind, he has absolutely no regrets. And why should he? Life, for Gerrit Cole, at this exact moment in time, is truly beautiful. And every step he’s taken to get here — predetermined or not — has been exactly the right one for him. That includes signing with the Pittsburgh Pirates after college as the first pick in the 2011 MLB draft; making his big league debut in 2013 as the National League’s Rookie of the Month; becoming an MLB All-Star in 2015; and even his 2017-2018 off-season trade to the Houston Astros, where he became the 18th pitcher in history to strike out at least 300 batters in a season and broke a record for the most strikeouts by a Houston Astros pitcher in a single season. All roads led him here, where he is clearly meant to be.

“In the end, I’m on the team that I wanted to play for, and somehow, my journey feels complete,” he admits.

This statement couldn’t be truer, especially at this moment in time, and in this particular place. Post-photo shoot, we’re sitting in a suite at Montage Laguna Beach, just down the road from from his home in Newport Beach, California (which also happens to be the seaside town in which he was born and raised). It was here, at this picture-perfect, oceanfront resort, that he learned he had lost the 2019 American League Cy Young Award to Justin Verlander. But just a few years later — at the time of our interview of which is mere days away — he is taking home that prestigious trophy, which is awarded annually to the best pitchers in the MLB’s American and National Leagues. So, needless to say, though it’s storming in California today, this visit is vastly better than his last — and much more poignant.

“This is a very rewarding and validating time,” Cole says. “I’ve made a few runs at this award, and I’m certainly proud of the work that I’ve done in the past. But this year felt special from the beginning: the people around me on the team and our coaches really bought into it, and it just seemed like they were there with me. Not that this wasn’t the case in past years, but it felt uniquely so this year. To be able to do it for this organization, where there’s so much history and so many great players, is incredible. It feels good to contribute to the greatness of the Yankees.”

Photo Credit: Mark Hanson

He’s been doing so since his very first game on July 23, 2020, during the peak of the Covid-19 pandemic. Which, when you’ve been waiting your entire life to play for your dream team, was a slightly underwhelming, anticlimactic start given the empty, fan-free stadiums.

But Cole is pragmatic. “I try to keep perspective when I talk about that time, because there were unfortunate things that happened to all of us. I was still able to play a season, be healthy, and take in some salary. My wife was pregnant at that time [with their first child, Caden; their second son, Everett, was born last year], and gave birth in the middle of the pandemic, which definitely put a strain on our family. But I’m really blessed to have come out of it with a healthy kid and an amazing wife that held it all together and made it all work somehow.”

As did he — in a big way. He’s been crushing it ever since making his Yankees debut as the Opening Day starting pitcher, throwing five innings against the Washington Nationals and allowing just one hit. That very first year, his regular-season winning streak reached a high of 20, the third-longest in MLB history. His inaugural season ended with a 7–3 record, throwing to a 2.84 ERA in 73 innings and striking out 94.

During his tenure with the team, he’s been pivotal to its success, and personally, broke a slew of records to boot. On September 29, 2020, in his Yankees playoff debut, he struck out 13 batters without a walk during Game 1 of the wild card series against the Cleveland Guardians, tying Tom Seaver for the second most in Yankees franchise history. He also became the first Major Leaguer in history to win three postseason games with 12 or more strikeouts. In his second season, he notched his 1,500th career strikeout, becoming the second fastest pitcher in history to reach the milestone behind Randy Johnson. He finished the 2021 season with a 3.23 ERA and 243 strikeouts in 181+¹⁄₃ innings over 30 starts, leading the American League with 16 wins and a 5.93 strikeout-to-walk ratio. That year, he finished second in American League Cy Young Award voting behind Robbie Ray. In his third year, he became the third fastest pitcher in MLB history, just behind Chris Sale and Pedro Martínez. All of which make the unanimous 2023 American League Cy Young Award vote more than well deserved.

Although he’s grateful for the award, his end goal, of course, is a World Series win. And he has definitive ideas about how he and the Yankees will make it rain (figuratively speaking of course) in his fourth season.

“This new season means new hope. It’s a fresh start,” he acknowledges. “We’ve added some high-quality players and we’ve gotten players that were injured last year healthy. The best part of the Yankees is [team owners, the] Steinbrenner family, and they’re just going to refresh [the team] the best they can every single year, and the level of competitiveness here is second to none. The hope is to win the World Series, and our club is certainly positioned within striking distance of doing that.”

While Cole says he isn’t doing anything radically different to make that happen (as the current Cy Young Award winner, does he really have to?), he’s still pushing himself to be the best that he can be — a player currently defined by his power pitching, four-seam and two-seam fastball, who has clocked throws as high as 102 miles per hour.

“I always have the pilot light on at this point, and right now, I’m just getting prepared to throw during those first few days of Spring Training. Those days are oftentimes the most important, and you want to be prepared. I really leaned on a new pitch — a cut fastball — that had taken me a couple of years to master toward the end of last year, so I’m looking forward to taking the new few steps there. I’m just trying to emphasize coming out of the gate with everything relatively ready to go, and I’m physically in a good spot to hit the ground running.”

Or pitching, as it were.

Photo Credit: Mark Hanson

   Playing for the Yankees has a few perks (just kidding, it has many), but for Gerrit Cole, they’re mostly food-related. He has a hit list of restaurants a mile long that he wants to try. His master plan is to take much more than a bite of The Big Apple.
Cole is a quiet kind of guy, but he lights up when talking about food and wine — especially when it comes to the food and wine of New York. He loves to cook, and his father — who seems to be a sommelier in training — prompted his love of cabernets and more.

“Food and culture are the best things about living in New York,” he enthuses. “I can eat the best of any cuisine in the world there.”
He rattles off eateries like West Village staples Anton’s and L’Artusi, Milos downtown, NoHo’s private members’ club Zero Bond, Mr. Chow, and Avra on the Upper East Side, with Daniel Humm’s Eleven Madison Park and Eric Ripert’s Le Bernardin — both three Michelin starred — as his imminent “musts.”

But having the ability to chomp his way through the core of the city isn’t the only thing he loves about it— it’s just what he loves the most. “Every time I come home to my apartment, the city is buzzing at midnight. There’s nothing like it. [Since the pandemic ended] the sense of community is back; the energy is back. The fans are so passionate, and the atmosphere is just electric. Every single day matters. As a player, it’s a real opportunity to play here.”

He’s finding that now, more than ever, there are opportunities in the city that never sleeps, and it’s opened up a whole new world to his relaxed,Cali-boy self. “Being from California, we have a disposition about us where we’re a little more laid-back, more chill, and a little more focused on the beach and whatnot. But here, you have so many different industries mingling and networking, you’re always meeting new people, and that’s exciting for me,” he explains.

And although New York is not directly responsible for its creation, the city is certainly where the actualization of his non-profit, the Gerrit and Amy Cole Foundation, came to be. The goal of the charity, which was founded in 2020 — the year Cole began playing for the Yankees — is to help improve the standard of living for children across the country. “Before we started the non-profit, we had a lot of involvement in the communities that we were in. We’ve always been trying to give kids a better opportunity, whether it’s through education, by encouraging them to play sports, or sometimes just with a smile. The goal is to support some aspect of their lives. We did a lot in Pittsburgh, and also raised money for the community out there in Houston. And then, once the [Yankees] contract came in, we thought, ‘we want to take it to another level.’ We wanted to set something up that leaves a lasting legacy and hopefully, it’s something that extends beyond Amy and I’s lives into the generation of kids,” he confides. 

Photo Credit: Mark Hanson

He and Amy began dreaming up the foundation in 2019, but then the pandemic hit, so they expedited its creation as quickly as they could in order to help their new community of New Yorkers survive and thrive —which they did at first by helping to get supplies to the frontline as quickly as possible. “It all really kicked off during the pandemic, but since then, our mission statement is rather broad. We’re just trying to loop in the communities that affect children in all different aspects from pediatric cancer to the arts, really. We’re trying to expose kids to classical music and dance, and give them opportunities that they otherwise wouldn’t have had. At the same time, we’re really close with the organization PCRF, Pediatric Cancer Research Foundation, here in Orange County, trying to find a way to cure cancer in kids. We’re also donating to organizations that are managing the quality of life for kids that have cancer or are ill — even things like supporting their families, who might need money to keep the lights on while their kid is sick. We’re trying to cover all bases and make as much of an impact as we can. The idea is to keep this going for a long time.”

Although Cole is a long way from retiring (again, hello Cy Young Award winner), life after baseball has been something he’s been thinking about before he even played college ball. The future has always been as important to Cole as the present, if not more so. That said, focusing on the non-profit later in life is a major priority. “We’re just trying to take it one step at a time, and the idea is to get better and do more every single year. And so, every single year we send grants out, trying to expand, but we don’t want to bite off too much because again, the plan is long-term so that we can look back at this over two, three or four decades and hopefully think, ‘wow, look at the impact we’ve had and who we were able to help.’”

Cole also plans on having his own sustainable farm, cooking more, and drinking more wine. I mean, I did say he was a foodie. But will this former theater minor be creating a podcast with his brother-in-law Brandon Crawford? You know the one: a three-time All-Star and four-time Gold Glove Award winner, now a free agent who most recently played for the San Francisco Giants, who also moonlights as “DJ BC Raw.” They could most definitely give the Kelce brothers’ “New Heights” a run for their money.  “It would be a fun podcast,” he admits. “I mean, he’s a great dad, a fantastic father and husband, a two-time world champion, and the greatest shortstop of all time. He’s got a lot to bring to the table.” For his part, Cole would be talking about — what else? — food and wine. But until those days arrive where he can just eat, drink, and be merry, he’s thinking of course about the (near) future, with the immediate goal of a World Series win. Outside of that, there isn’t much he could really ask for, because Gerrit Cole has everything he ever dreamed of, and maybe more —  today, tomorrow, and forever.

Photo Credit: Mark Hanson