The day the 2008 MLB draft started, Gerrit Cole, one of the best high school pitchers in the country, went golfing with his friends. He had a fastball that touched the high 90s and all the makings of a front-line starter, but he did not expect to be selected early.
Leading up to the draft, Cole and his handlers had informed every team that he intended to go to UCLA. Scott Boras, Cole’s advisor, had told teams it’d take a “substantial bonus” for him to sign. From what Cole’s camp had been hearing, that message had scared most teams away.
Then the New York Yankees called. Cole’s favorite team had taken him in the first round, No. 28 overall. Cole called his pitching coach, Zak Doan.
“I just remember him screaming, going, ‘What the heck!’ Doan said. “We were all shocked they picked him.”
More than a decade later, this remains one of the best what-if moments in baseball history because of what happened next. Cole never pitched for the Yankees. He attended UCLA, was selected No. 1 overall in the draft three years later and became one of the game’s best pitchers.
This postseason, he has been mowing down hitters for the Houston Astros. In two starts, he has 25 strikeouts and a 0.57 earned-run average. He’s a strong candidate for the American League Cy Young Award.
Tuesday, in Game 3 of the AL Championship Series that is tied 1-1, Cole will pitch against the Yankees in the Bronx. His father Mark, who helped guide him through the draft decision in 2008, will be in the stands.
During Gerrit’s senior year at Orange Lutheran High, his father created spreadsheets, crunched numbers and projected how his son’s financial future might look if he entered pro baseball after high school, or if he waited until after three years of college. He accounted for taxes and agent fees, various investment strategies, and potential big-ticket purchases, such as a house or a car.
After much discussion, the Coles decided Gerrit would attend UCLA. He would learn under coach John Savage, work toward a college degree and still be only 20 years old for the 2011 draft. Mark even took out a sizable insurance policy to protect Gerrit in case of injury while in college.
The Coles had been holding firm in that decision until the Yankees called.
“I thought the pick deserved some serious thought,” Gerrit said. “We kind of reevaluated the process after that happened.”
One factor: Gerrit had grown up a huge Yankees fan, with a Derek Jeter poster on his bedroom wall. He had attended Game 7 of the 2001 World Series in Arizona, clutching a sign that read, “Yankee Fan Today, Tomorrow, Forever.” He’d inherited his fandom from his father, who spent part of his childhood in upstate New York.
Ultimately, though, the Coles reached the same conclusion: Gerrit would go to college first.
“We just felt confident sticking with the plan,” he said.
Mark remembers having a conversation with the Yankees about two to three weeks before the signing deadline, and having to break the news. The team wanted to fly to California, meet the Coles, give a sales pitch.
“And I said to them, ‘Since there’s no chance that this is going to happen, Gerrit wants to go to UCLA, there’s no reason to sit down,’ ” Mark said.
He felt as if they would be unfairly leading on the Yankees by even meeting.
“There were never any discussions,” he said. “There was never a meeting. There was never a negotiation.”
Boras said the Yankees made “a very qualified offer.” But Mark maintains that the family never discussed specific dollar figures with the team. In fact, he says, the family never spoke with the Yankees after turning down that meeting.
“There was some disappointment [on the Yankees’ side],” Mark said, “because they wanted to have a chance. But the decision had already been made.”
Boras, Cole’s agent, echoed that sentiment.
“This was not about the Yankees,” he said. “It was really about what’s the best time for Gerrit to enter pro baseball.”
After the 2017 season, the Yankees had a chance to nab Cole when the Pittsburgh Pirates, the team that drafted him No. 1 overall and for whom he pitched for five seasons, dangled him in trade talks. But Yankees general manager Brian Cashman reportedly balked at the asking price and Pittsburgh shipped him to Houston, where he has flourished. He was 15-5 with a 2.88 ERA and 276 strikeouts in 2018, and 20-5 this season, when he led the AL with a 2.50 ERA and 326 strikeouts.
After this postseason, Cole will become a free agent and the Yankees may get a third crack at him. They need help in their starting rotation and traditionally have been willing to pay for top-tier free agents. Could he end up in pinstripes? Boras chuckles.
“Well, Gerrit Cole is a Houston Astro. That’s all I know for now,” Boras said.