New York insiders predict Yankees’ Aaron Judge contract extension

On Opening Day, when Brian Cashman took to the podium prior to first pitch and announced to the masses that he and his team had failed in an effort to secure a contract extension for Aaron Judge, the Yankees‘ season seemed to be starting with a pall over it.

Weeks later, despite an Opening Day walk-off against Boston, the team was mired at 7-6, showing the same sort of offensive futility that had plagued them the year prior. Judge seemed to be caught up in the malaise, too, delivering on occasion, but only when it was unimportant. “Bet on yourself, huh?” was on the verge of becoming the dominant rallying cry.

From that moment in Detroit on, though, the Yankees have been a house aflame, and Judge’s superhuman two-month stretch — featuring a number of starts in center field — has led the way. The Yanks have gone 33-10 since the Twitterverse declared them dead (and, worse yet, boring), and Judge has reached totals of 22 homers, 45 RBI, a .311 average, and a 1.058 OPS in a depressed offensive environment.

In essence, he’s made himself into the kind of singular figure the Yankees, of all teams, can’t afford to lose. He’s the face of baseball on Roger Maris’ pace. He’s the brand in the Bronx. And it might be time for the team to consider reneging on their promise not to talk turkey in-season.

Prior to the campaign, the Yankees offered Judge an (at the time!) fair extension offer of seven years for $30.5 million annually, plus $17 million for 2022, his final year of arbitration. Essentially, eight years and $230.5 million.

Judge’s reported counter? Nine or 10 years at $36 million per season. It’s an outlandish request, based on length, but it’s also … basically what Gerrit Cole received two winters ago (nine years, $324 million).

So … where might we net out? Jon Heyman, who reported the first counterproposal (which seemed less than serious at the time, and deadly serious now), shared his thoughts on a potential midseason deal with Joel Sherman.

Yankees Aaron Judge extension projections for midseason

While Heyman doesn’t believe Judge is in line for the length he was reportedly seeking, he’s now admitted that $36 million for seven years feels more fair for a midseason update. As the MLB insider stated, “At this point, it’s really hard to argue he deserves less than $36 million. They’ve already paid Cole $36 million!”

Heyman also made the excellent point that the monstrous offer Judge desired before the season began … may have even increased after his first half that has him on pace for over 60 homers. If you believe the Yankees are going to have to raise their offer, why wouldn’t Judge also raise his estimate, especially after all that he’s proven through early June?

The final years of the Judge contract will be unsavory, no matter what the total dollars. It’s a price the Yankees legitimately have to pay, though, based on the overall body of work and Judge’s scorching first half.

Cashman can continue to play chicken into the playoffs if he really wants to, but this is becoming a more dangerous gamble (for one side) every day.

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