On a cold December morning in the Bronx, Gerrit Cole walked into the Yankees’ ownership suite high above the field at Yankee Stadium. With his wife, Amy; his agent Scott Boras; and a few others in tow, Cole received a warm welcome from Yankees managing general partner Hal Steinbrenner, general manager Brian Cashman, manager Aaron Boone and several other Yankees officials who were counting down the minutes before the sharply dressed and newly clean-shaven 29-year-old inked his name to the largest contract ever given to a pitcher. After the group spent a few minutes discussing everything from college football to the Coles’ trip to the Big Apple, Cashman and Boras sat down at a round, dark wood table and put the final touches on a power-shifting contract that represented so much for so many people.
For Cole, a Newport Beach, California, native who compiled a 94-52 record with a 3.22 ERA in seven Major League seasons, the thick stack of papers symbolized the realization of a lifelong dream. For Boone, it meant that he had a starter capable of going toe-to-toe with any other pitcher in the sport. For Cashman, the document was the end of a long and winding pursuit. Yet for everyone in the room, it marked the beginning of a different chase.
While Boras and Cashman dotted the i’s and crossed the t’s, Cole calmly walked up to the bar situated in the back of the room and asked the bartender for a pen and a sheet of paper.
The bartender handed Cole a pad featuring a Yankees logo and a pen.
“I have to write down a few notes for my press conference speech,” Cole said. “I don’t want to forget to thank anyone.”
As Cole penned the note he longed to write since childhood, Boras asked him to come to the table. The pitcher folded the paper and placed it in his pocket. He quietly thanked the bartender and took a seat next to his agent. Within minutes, Cole had signed a nine-year contract to pitch for the Yankees.
“Thank you,” Cole said, this time addressing Steinbrenner and the other Yankees officials in a not-so-subdued tone.
The realization that Cashman had finally reeled in the man he described as his “white whale” filled the air as much as the aroma from the lunch spread a few feet away.
For a general manager who has presided over four championship teams and who has a track record of bringing as many star players to his club as any executive in the game over the last two-plus decades, the white whale label was a bold statement. Cashman and his team have certainly landed some of baseball’s biggest fish. The GM brought Roger Clemens to the Bronx on the heels of the Rocket’s two consecutive American League Cy Young Awards with the Blue Jays. Cashman signed Jason Giambi after the first baseman had established himself as one of the most feared hitters in the sport. Alex Rodriguez came to New York on Cashman’s watch, as did CC Sabathia, Mark Teixeira and A.J. Burnett, all of whom helped deliver a championship in 2009. The MVP of that World Series, Hideki Matsui, was also recruited and signed by the Cashman regime.
But, when considering how much effort Cashman had previously put toward getting Cole into pinstripes and how the right-hander had rebuffed those efforts while rising to the top of his profession, the characterization made perfect sense.
The Yankees selected Cole out of Orange Lutheran High School in California with the 28th overall pick in the 2008 draft. Back then, Cole’s fastball was already clocked between 98 and 100 mph, and his intensity and intelligence were equally impressive.
Cole had another unique characteristic: From the time he was a child, he had rooted for the Yankees. The passion Cole had for the pinstripes was passed down from his father, Mark, who spent part of his childhood in upstate New York.
Cole’s fervor was real. He and his family made cross-country trips to attend games at the old Yankee Stadium, and during the 2001 World Series, an 11-year-old Cole brought a sign to Bank One Ballpark in Phoenix that read “Yankee Fan Today Tomorrow Forever.” A photo of the young fan holding the sign and donning a pinstriped jersey and Yankees hat was published in The Star-Ledger (Newark, N.J.) at that time.
“The way the Yankees went about playing the game set an example for every kid when I was growing up,” Cole said from the suite. “They had such great competitors in that era. I relished the pitching matchups between Roger Clemens and Pedro Martínez. I loved watching David Wells pitch in those big October games. Derek Jeter was one of the all-time greatest Yankees, and Bernie Williams was as stoic as you could get. Paul O’Neill wore his heart on his sleeve. I idolized those guys because of how hard they played the game and because they delivered in the clutch. The Yankees brand has always been the gold standard, and I’m looking forward to contributing to that now.”
While it may have appeared that this match was meant to be, a union would not happen in 2008. Cole instead decided to pursue the dream of pitching for a big-time collegiate program, and headed to UCLA.
Three years later, the Pittsburgh Pirates made Cole the No. 1 overall pick of the 2011 draft, and after making his Major League debut in 2013, the starter quickly validated that decision. Cole helped the Pirates reach the postseason in each of his first three years in the bigs, culminating in a 2015 campaign in which he posted a 19-8 record and made his first All-Star team.
Realizing that re-signing Cole to a free-agent contract was not financially feasible, Pittsburgh began the process of shopping one of the game’s bright young pitchers prior to the 2018 season. Cashman entered the Cole sweepstakes, but once again, he was unable to net the prized pitcher.
Despite offering the Pirates a competitive package of players, Cashman was outbid by the Houston Astros, the team that had just defeated the Yankees in a seven-game battle in the 2017 ALCS.
Cole was dominant in 2018, posting a 15-5 record and recording a 2.88 ERA and 276 strikeouts. Then, he took his game to an even higher level last season, winning 20 games and leading the American League with a 2.50 ERA and 326 strikeouts. After making his second straight All-Star team with the Astros, he finished runner-up in the AL Cy Young voting to teammate Justin Verlander.
For the second time in three years, the Astros and Yankees met in the ALCS, and Cole took the mound for Houston in Game 3 at Yankee Stadium. As if Cashman didn’t already know what Cole was capable of, the free agent-to-be tossed seven scoreless innings, and in the process gave the Astros a 2-games-to-1 series lead.
Cashman’s team was denied a trip to the World Series, losing to Houston in six games. But the GM was determined to bring Cole to the Bronx in the wake of the 2019 season, and after meeting with him at his home in California, where he surprised Cole with two of his favorite bottles of wine, Cashman finally got his white whale into the boat.
Now, standing in the famed Stadium that Cole will call home, the buoyant group posed for a few photos in the owner’s suite, then headed to the Stadium’s Legends Club for Cole’s introductory press conference. When Cashman spoke, he immediately reflected on the long journey that Cole took to New York.
“When we drafted Gerrit with our No. 1 pick several years ago, we knew that he was a Yankees fan growing up,” Cashman began. “When you pause and think about the decision that he was forced to make at that time -- either going pro as a first-round pick, making a lot of money, or continuing on with a college education at a great university in UCLA -- you reflect on the discipline, poise and patience that he had to work through. As he continued his amateur career, we sat back and watched him grow. We continued to watch him hone his craft and develop in Pittsburgh, and then we got a chance at that apple again two years ago. Unfortunately, he wound up with Houston, and he again showed discipline, poise and patience, giving away opportunities to sign a contract extension there.”
Cashman then made the point that this was the perfect time for Cole to join the Yankees.
“He put himself in a position to have a full conversation with all people involved, including the New York Yankees,” Cashman said. “Now he’s here. The right time, the right place. Both mentally and physically, he waited until he was as prepared as he could possibly be to enter this time and place. I think that all of the experiences he has had along the way have put him in position to contribute in a significant way with everyone else around him. This is a very historic signing.”
A few minutes later, Cole put on a Yankees cap and his No. 45 pinstriped jersey for the first time.
“I’d like to start with something that’s pretty special to my heart,” Cole said as he reached below the podium and revealed the faded sign that he had brought to the 2001 World Series as a child. “I’d just like to say, ‘I’m here. I’ve always been here.’”
As morning turned to afternoon, Cole sat down with a group of beat writers. Among the topics he covered, one of the first brought him back to his childhood and specifically that fateful trip to Arizona.
“That’s the sign,” he said. “That’s the same one. It’s 18 years old. I had it on my wall for a few years, and that’s why it faded. I didn’t actually make the sign. We were staying at the same hotel as the Yankees, and there was an arts and crafts area set up on the club level. Another family had made the sign and brought it to Game 6. They didn’t have tickets for Game 7, so they gave it to me to bring to that game. We got to the game early, and I got a ball from Derek Jeter.”
From a sentimental moment that took place in the distant past to a more recent one, Cole shed some light on the significance of the now famous bottles of wine he was given during his early December meetings with the Yankees.
“There are some visiting clubhouse guys that are really close to my heart, and [Yankees director of clubhouse operations] Lou Cucuzza Jr. is one of them,” Cole said. “I have always come into Lou’s office, and we have talked about stuff. One day, we were talking about a trip that my wife and I took to Italy for our anniversary, and I showed Lou photos of a wine cellar that we ate at in Florence. There was a bottle of Masseto on the table, and he asked me what it was. I told him that it’s acknowledged as the second-best merlot in the world, and that it’s definitely my favorite bottle.”
The conversation’s specifics faded from Cole’s mind until a most-unusual surprise during his meeting with Yankees brass.
“Aaron (Boone) handed me a couple bottles of Masseto, including one that was the exact 2004 vintage from the anniversary dinner that my wife and I had had in Florence,” Cole continued. “I couldn’t figure out how they could have pulled that off, and later that night, as I laid my head down on the pillow to go to sleep, it finally hit me. I remembered the conversation with Lou.”
Just like those bottles of wine, it’s no secret that Cole has gotten better with age. He has been able to blaze his fastball past hitters since high school, but the mental adjustments he has made have elevated him to one of the game’s best pitchers.
“I have leaned on my fastball command throughout my career,” Cole said. “Now I’ve switched the grip from mostly throwing with a two-seam grip to throwing with a four-seam grip more often. I saw what my true strengths were relative to my peers, and I made that adjustment in an attempt to lean more on what I do well. I have tried to stay creative and unpredictable along the way. I’m always trying to figure out if a hitter has a weakness or a bruise. Sometimes you poke the bruise early in the at-bat and let hitters know that you know where the bruise is. Other times, you lean on your strengths early and then go to the bruise when you need it. It’s a chess game in that sense, and it really gets heightened as the games get more important. I’m going to bring everything that I’ve learned to the Yankees.”
Having already taken the ball in October, especially during his recent ALCS start at Yankee Stadium, will inevitably help Cole during his tenure in the Bronx.
“Pressure is a privilege,” he said. “Pressure comes in situations that you’ve earned. You get to pitch in games in October because you’ve pitched well all year. With that in mind, you need to stick to the process you’ve used up to that point. We can say that it’s just another game, but when it gets to October, it’s really not. When I pitched against the Yankees in the ALCS, I knew that I needed to stay focused and pitch well. I feel like I was able to do both of those things.”
Cole is aware that he will face more pressure in the upcoming seasons than he did in the past. For a Yankees team that nearly made it to the World Series in two of the last three seasons, bringing in one of the best pitchers in the game has significantly heighted the already-lofty expectations.
“I love it,” Cole said. “That’s what you play for. I want to compete every year for a championship, and I want to win a championship. It doesn’t scare me; it’s what I dreamed of.”
After all the photos were taken and almost as many questions were answered, Cole’s whirlwind first day in pinstripes was nearly complete. He had one last interview, and from the batting cages outside of the home clubhouse, he spoke about a journey that has come full circle.
“I feel really lucky,” he said. “I didn’t think it was going to work out like this when I made the decision to go to UCLA coming out of high school. But this is the ideal scenario. I know that the decision I made back then was the right one because I had experiences in college and in my first seven big league seasons that have shaped me into the person I am today. Getting to finish it off where I always wanted to be is the icing on the cake.”