The Yankees’ season ended in disappointment when the Blue Jays eliminated them in the ALDS. The loss has triggered familiar debates about missed opportunities, particularly the 2019 Bryce Harper free agency. Jon Heyman of the New York Post reported that Bryce Harper was keen on joining the Yankees. Harper’s father was a New York fan, and he wore No. 34 with the Washington Nationals to honor Mickey Mantle, who wore No. 7. Interestingly, the digits in 34 add up to 7. Instead, the Bronx front office passed, Bryce Harper signed with Philadelphia, and his bat has dominated ever since.

But according to HOF CC Sabathia, there’s an even bigger miss—one that became painfully relevant this season. That player is Manny Machado.

CC Sabathia didn’t mince words in his recent social media exchange with The Yankee Report. When asked whether passing on X is the biggest mistake by the Yankees besides passing on Bryce Harper. At first, he took a sarcastic dig at Harper by commenting, “Sure. lol he hasn’t won anything. Matter of fact his team won after he left haha. You can be a great player, but not a winning player. I think we in the same spot if we had singed him.” He was referencing that the Nationals won the 2019 World Series, the same year Harper departed for Philadelphia. And then HOF stated, “I think Manny was a bigger miss imo.”

The four-time All-Star was repeatedly linked to the NYY during the 2018 trade deadline and the following offseason. Despite the Yankees’ need for a third baseman, they didn’t meet his asking price, and he went on to sign a record 10-year, $300 million deal with San Diego (later extended to 11 years and $350 million). Instead, the Bronx opted for DJ LeMahieu and Gio Urshela, who haven’t matched Machado’s star power in San Diego.

When you look at Machado’s form, Sabathia’s statement makes more sense. This season, he reached career milestones, such as hitting his 350th home run and 2,000th hit in 2025.

He has also proved that he can still come through at critical moments, like when he hit a single home run in the ninth inning to give the Padres the win over Atlanta. If he had been in New York’s lineup, his presence at third base (or somewhere else) could have changed the way the team played and how they built their lineup in important games.

Sabathia’s perspective carries weight that goes beyond.

He’s a Hall of Fame pitcher who won a championship with the Yankees and understands the pressure of performing under the brightest lights in baseball. When he says Machado was a bigger miss than Bryce Harper, it makes sense. Looking at how Harper’s bat went silent in the postseason only adds more weight to Sabathia’s comment.

As the Yankees head into another long winter, and Machado and Harper are no longer in the picture, the team must now address more immediate roster concerns.

Winter moves: Stabilizing the infield and rescuing the relief corps

With Machado and Bryce Harper off the table, the NYY’s main offseason goals change from going after stars to fixing concerns inside the team, such as Volpe’s growth, Cody’s deal, the outfield, and the bullpen deficiencies.

As the Yankees head into another long winter, the team must focus on stabilizing the infield and rescuing the relief corps. Re-signing Cody Bellinger should be a primary priority after he hit 29 home runs in 2025 with a slash line of .272/.334/.480, making him the team’s second-best player in WAR behind Judge.

The Yankees also face uncertainty at shortstop, where Anthony Volpe went 1-for-14 in the ALDS after three consecutive underwhelming offensive seasons. New York can’t keep going with him without competition; they need to either upgrade or have a strong backup plan.

When it comes to pitching, the beginning rotation gives us hope. The Yankees will get back Max Fried and Carlos Rodon, and Gerrit Cole is projected to be back in the first half of 2026. Rookie Cam Schlitter should get a full season, while Will Warren, Luis Gil, and maybe Clarke Schmidt (who is coming back from Tommy John surgery) fight for positions on the back end.

The bullpen represents the most glaring weakness heading into the offseason.

New York had a 4.37 bullpen ERA, which was the worst in the playoffs and 23rd in MLB. In 2025, just three relievers pitched more than 50 innings, and Luke Weaver and Devin Williams are about to become free agents. They’ll need to look for good arms who can strengthen the late-inning, and who can do more than one job to stop the bleeding.

The NYY front office must start taking action. Keeping Bellinger, addressing Volpe’s struggles, and building a reliable bullpen are interconnected steps that will determine whether they exit winter with hope or excuses. Sabathia’s comments are a reminder that championship opportunities vanish quickly, and the cost of hesitation rises over time.