The baseball that left Freddie Freeman’s bat last October still haunts Nestor Cortes‘ dreams. Now wearing Milwaukee Brewers blue instead of New York Yankees pinstripes, the veteran left-hander is trying to move forward while still processing the moment that altered the trajectory of two franchises.
“I hate how it happened,” Cortes said from the Brewers’ spring training facility. “Trust me, I [wasn’t] able to sleep after that, just because I replayed it in my head every single time.”
The pitch that changed everything — a fastball that didn’t get high enough inside to the three-time MVP — resulted in the first walk-off grand slam in World Series history. That moment in Game 1 sent the Yankees spiraling toward an eventual six-game defeat and propelled Cortes toward an unexpected change of scenery.
Traded to Milwaukee in December as part of the deal that sent All-Star closer Devin Williams to New York, Cortes now finds himself balancing twin challenges: integrating with a new team while processing the lingering pain of what might have been.
Finding his place in Milwaukee
Cortes has already taken steps to ingratiate himself with his new teammates. He arranged for a coffee truck to visit Brewers spring training, recreating a tradition he had established with the Yankees.
“I just wanted to give the guys here something to look forward to,” Cortes explained. “And a lot of guys would say thank you to me, so it’s a good way to learn their names.”
The gesture represents the personal side of a significant baseball transaction. For the Brewers, acquiring Cortes addresses a critical need in their starting rotation following another competitive offseason that saw several key departures, including Williams and shortstop Willy Adames.
“It’s always a combination of things for us,” said Brewers general manager Matt Arnold. “Whether it’s present value or future value, we want to try to help the team win a championship. You can’t replace a guy like Devin Williams, but the ability to get an established starter like Nestor and a young guy like [Caleb] Durbin, who has a chance to impact our infield, is pretty exciting for us.”
With one year remaining before free agency, the 2025 season represents both an opportunity and an audition for Cortes. A strong performance could position him as either a cornerstone for Milwaukee’s future or a valuable trade chip if the Brewers find themselves sellers at the deadline.
The pitch that changed everything
What makes Cortes’ situation particularly poignant is how close he came to being a Yankees postseason hero rather than the pitcher who surrendered one of the most devastating home runs in franchise history.
Protecting a one-run lead in the 10th inning of Game 1, Cortes had already navigated dangerous waters by retiring Shohei Ohtani and intentionally walking Mookie Betts. One out away from securing a crucial road victory, he executed his game plan against Freeman — attack inside with a fastball — but left it fractionally too low.
“It was in enough, but low,” Cortes recalled. “And he’s known for going the opposite way. His game is a left-center field. So for him to turn [on] that pitch, I give him all the credit.”
The resulting grand slam changed the series’ momentum irrevocably. Instead of the Yankees returning to New York with a split, they faced mounting pressure that ultimately proved insurmountable.
“We had done enough to win that game,” Cortes reflected. “They can talk whatever they want to talk, but we win Game 1—which we should have—we lost 2 and 3, we win Game 4 and we should have won Game 5. Then we go back to L.A. up 3 to 2.”
Despite the lingering frustration, Cortes acknowledges the ultimate outcome. “They deserve all the credit in the world, they won the World Series,” he said. “At the moment, they showed they were the better team.”
Historical precedent offers hope
Baseball’s long history provides context and perhaps comfort for Cortes. He’s not the first pitcher to surrender a devastating World Series home run, nor would he be the first to find redemption afterward.
Hall of Fame reliever Dennis Eckersley experienced similar heartbreak when Kirk Gibson hit a walk-off home run against him in Game 1 of the 1988 World Series. The very next season, Eckersley closed out a championship for Oakland, completing a remarkable redemption arc.
When asked if a similar storyline with Milwaukee would help ease the pain, Cortes smiled. “Ha,” he said. “It would if it happens here.”
Milwaukee’s championship aspirations
The Brewers have been perennial contenders in recent seasons, capturing the NL Central title in three of the past four years. However, the franchise has never won a World Series, with their lone appearance coming in 1982.
Cortes joins a team that has consistently overperformed expectations despite operating with financial constraints that pale in comparison to markets like New York and Los Angeles. His addition provides a proven left-handed starter to a rotation that will need stability following significant bullpen changes.
For both Cortes and the Brewers, 2025 represents an opportunity to write new chapters. Milwaukee seeks its first championship in franchise history, while Cortes aims to add a redemptive postseason performance to his resume.
As spring training progresses and the regular season approaches, Cortes will continue processing last October’s disappointment while embracing his new surroundings. The memories haven’t faded, but with each passing day in Milwaukee, the opportunity for a fresh start grows more tangible.
One thing remains clear — baseball’s capacity for both heartbreak and redemption continues to shape Cortes’ journey, even as he trades his Yankees cap for Brewers blue.
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