Inside The Pinstripes

Yankees Recognize What's at Stake as Aaron Judge Enters Free Agency

Brian Cashman and Aaron Boone spoke about Aaron Judge during Friday's end-of-season press conference, reiterating that they want No. 99 back in pinstripes.

Max Goodman

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NEW YORK — As the Yankees brace for Aaron Judge to officially enter free agency over the next several days, New York's plan of attack for bringing their superstar slugger back to the Bronx hasn't changed. 

"To restate what has been stated by me and ownership and Aaron Boone and anybody related to the Yankees, we'd love to be able to bring Aaron Judge back and have him maintain being a member of this franchise," Yankees general manager Brian Cashman said in a press conference at Yankee Stadium on Friday. "The career path he's currently on his Hall-of-Fame like and nothing better than to have him continue to man right field for us and impact us both on and off the field the way he has thus far."

It's been almost exactly six months since Judge turned down a lucrative extension that was offered by the Yankees leading up to Opening Day, a self-imposed deadline from Judge designed to prevent his contract situation from becoming a distraction during the regular season. Rather than taking the $213.5 million over seven years from New York, Judge bet on himself, producing one of the best seasons by a position player in MLB history.

Judge, who turns 31 in April, smacked 62 home runs, setting the new single-season record in the American League. The outfielder led the league in practically every offensive category, contending for a Triple Crown while earning a trip to his fourth All-Star Game. While others in pinstripes struggled, or missed time with injuries, Judge was consistent and reliable, appearing in a career-high 157 games, carrying his club to a 99-win season and a division title.

"I hope he's back and a Yankee for forever," manager Aaron Boone added on Friday. "I can't think of a better guy that you'd want to be leading your team and leading your organization and hopefully that all works out."

Considering Judge is going to enter the open market, an expensive asset that plenty of contenders are poised to pursue this winter, there are no guarantees that No. 99 will don pinstripes on Opening Day next season. After all, the ball is in his court. He can take his time in free agency, listening to offers while considering if he wants a change of scenery. 

From a financial standpoint, Judge played his way to a significant pay raise from New York's offer in April. Producing another MVP-caliber season, showing he can stay healthy, Judge might set a record for average annual value in whatever deal he signs over the next few months. 

The Yankees understand that Judge brings more than elite production between the lines. He doesn't just help them improve their chances at winning a championship, he's one of the faces of this sport, a player that brings immense value and revenue that puts fans in the stands. 

To use Cashman's words, "certain individual players transcend the team and everything stops when they're at bat or they have the ball in their hands."

"He's a fan favorite, he interacts with our fans extremely well, he's respected within that clubhouse, goes about his business as good as you possibly can, he's an elite performer and one of the game's best, if not the best player," Cashman explained. "With all that being said, those are the type that you want to retain and have as long as you possibly can."

Ultimately, the Judge sweepstakes will come down to how much owner Hal Steinbrenner is willing to spend and if Judge simply wants to wear a new uniform. Considering the latter, Judge's future is out of the Yankees' control, to a certain extent. Perhaps he prefers to return home and play for the Giants, link up with some other superstars on the Dodgers or go from the Bronx to Queens, signing with the Mets. 

The Yankees will need to find that balance between doing whatever it takes to get Judge to return and making a sound business decision. If Judge makes them wait until next spring, before signing elsewhere, it would put the Yankees in a tough spot when it comes to filling his shoes, fielding the best roster possible to end their 13-season World Series drought. That said, New York understands what's at stake. The future of this franchise flows through Judge's decision, a choice that will have the attention of the entire baseball world all offseason long.

“Hal Steinbrenner will collect all the information from the industry standpoint, where people are in free agency, things can get pretty crazy," Cashman said. "Then obviously factor in everything else that are non-baseball related. What drives our fan base, showing up and supporting us. [Steinbrenner] wants to make them happy. … Hopefully we’ll have some positive conversations that lead to the outcome that we want. But we’ll see.” 

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Max Goodman
MAX GOODMAN

Max Goodman covers the New York Yankees for Sports Illustrated and FanNation. Goodman has been on the Yankees beat for three seasons. He is also the publisher of Sports Illustrated and FanNation's Jets site, Jets Country. Before starting Inside The Pinstripes, Goodman attended Northwestern University and the Medill School of Journalism. He earned his Bachelor’s Degree in Broadcast Journalism and Master’s Degree in Sports Media, graduating in 2019. At school, Goodman was an anchor and reporter with NNN SportsNight and played on the club baseball team. While at Northwestern, Goodman interned with MLB.com as an associate reporter covering the Miami Marlins. He also interned with ESPN, working as an associate reporter on Mike Greenberg's Get Up. Goodman is from New York City. He grew up in Hell's Kitchen. Follow Goodman on Twitter @MaxTGoodman. You can connect with him via email by reaching out at maxgoodmansports@gmail.com.

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