Gary Sheffield Warns Aaron Judge About Leaving the Yankees

New York Yankees star outfielder Aaron Judge is only months away from potentially hitting free agency, and Gary Sheffield isn’t hoping to see the 30-year-old leave the Bronx anytime soon.

Then again, considering the three-time All-Star’s torrid start to the 2022 season, something tells us the Yankees and Sheffield have similar feelings right now.

After failing to reach a contract extension with the Yankees ahead of Opening Day, Judge began his seventh MLB campaign with nine home runs in his first 23 games. The 6-foot-7, 282-pound slugger is healthy, playing Gold Glove-caliber defense, and positioning himself to earn a massive contract next offseason.

The Yankees, in Sheffield’s humble opinion, are the team that should sign the 2017 Home Run Derby champion to such a lucrative deal.

“In his situation, I think that’s the perfect place for him to be,” Sheffield told Fox News Digital’s Ryan Gaydos. “Always leaving is not the answer. The grass is not greener on the other side.”

New York Yankees outfielders Gary Sheffield (L) and Aaron Judge.
Gary Sheffield (L) wants to see Aaron Judge stick with the New York Yankees | Matthew West/MediaNews Group/Boston Herald via Getty Images; Adam Hunger/Getty Images

Sheffield, who played for the Yankees from 2004-06, understands the importance of the hometown fan favorite. He spent his Yankees years playing alongside Bernie Williams, Derek Jeter, and Mariano Rivera, all of whom had their numbers retired after spending their entire careers with the Bronx Bombers.

Sheffield, a nine-time All-Star, also played with the likes of Robin Yount, Tony Gwynn, and Chipper Jones, three baseball legends who played exclusively for one team. Could you truly imagine Gwynn, the greatest player in San Diego Padres history, suiting up for the Baltimore Orioles? What about Jones, an Atlanta Braves icon, spending his final season in a Miami Marlins uniform?

Although it’s too early to suggest Judge will join those three in the National Baseball Hall of Fame, Sheffield does believe he’s already cemented himself as a player who would look strange in another uniform.

“In his case, when you talk about the Yankees, you think of Aaron Judge. When you think of Aaron Judge, you don’t think of him in Seattle or Boston or anywhere else. These guys got to come to that conclusion and start looking at what’s best for their future long term.”

Gary Sheffield

Sheffield might be speaking from experience after he played for eight teams in parts of 22 seasons. In hindsight, perhaps spending more time with a single organization would have helped his own Hall of Fame case.

Unfortunately for Sheffield, he’ll likely need to wait for the Yankees and Judge to agree on a new contract. There have been no credible reports of late suggesting the two sides will ink an extension during the 2022 season.

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