Will Aaron Judge’s ‘gamble’ with Yankees go down as best in MLB history?

MINNEAPOLIS, MN - JUNE 07: Aaron Judge #99 of the New York Yankees rounds the bases on his two-run home run against the Minnesota Twins in the first inning of the game at Target Field on June 7, 2022 in Minneapolis, Minnesota. (Photo by David Berding/Getty Images)
MINNEAPOLIS, MN - JUNE 07: Aaron Judge #99 of the New York Yankees rounds the bases on his two-run home run against the Minnesota Twins in the first inning of the game at Target Field on June 7, 2022 in Minneapolis, Minnesota. (Photo by David Berding/Getty Images) /
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Aaron Judge has arguably the most unique soon-to-be free agent situation in the history of Major League Baseball. It’s really not an exaggeration, either.

Prior to the season, he rejected a seven-year, $213.5 million extension from the New York Yankees, clearly indicating he knows he’s worth more from both a performance and marketing standpoint. He’d already proven the latter, but the former has been interrupted by injuries and a lack of overall team success in the postseason. His lone accolades heading into 2022 were three All-Star appearances and two Silver Slugger awards.

That’s not going to guarantee you something north of $35 million per year, given the success we’ve seen from other players who have landed some of the biggest contracts ever.

But now? Judge is the clear MVP frontrunner in the entire sport after his roaring start. Through 53 games, he’s hitting .315 with a 1.070 OPS, 204 OPS+, 46 runs scored, 22 homers and 45 RBI. Unbelievable.

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As we discussed not too long ago, Judge rejecting the Yankees’ final offer before Opening Day wasn’t exactly a “gamble,” despite it being referred to as such by just about everyone.

Any time you reject $213.5 million, however, it’s hard to not consider that a risk, since all it takes is an unspectacular campaign or an injury to lose a significant portion of that money. Then again, Judge (fingers crossed) has been a workhorse and is delivering in a way nobody else is.

Is Aaron Judge’s ‘gamble’ with the New York Yankees the best of all time?

When looking back over the last two decades of contracts, if Judge gets his reported desire of $36 million per year over at least seven years, it might be the biggest player victory for someone of this magnitude/star power.

It’s also more than likely the first of its kind! Recently, before the 2019 season, Anthony Rendon rejected an extension from the Washington Nationals (though the numbers were never truly reported), then proceeded to win a World Series and secure a $245 million deal from the Angels.

A similar situation happened with Max Scherzer back in 2014 with the Detroit Tigers, who offered the right-hander a long-term deal that would’ve made him one of the highest-paid pitchers in baseball. Scherzer rejected, followed up his Cy Young campaign with a top-five finish, and then landed $210 million from the Nationals.

And how about a previous similar situation involving the Yankees?! Remember when they reportedly offered Robinson Cano a seven-year, $175 million contract before the 2013 season? He rejected, finished fifth in the MVP voting that year, and then got $240 million from the Seattle Mariners in what turned out to be a colossal mistake the Yankees dodged. Cano’s career after that deal has mostly featured his epic downfall.

While rounding up the other biggest contracts in history, it seems guys like Mike Trout, Bryce Harper, Alex Rodriguez, Gerrit Cole, Albert Pujols and Manny Machado didn’t exactly take “risks.” They were all well-established talents with a considerable track record simply waiting for their time in free agency to come. Judge rejected the biggest known offer fans can think of and could make even more.

Despite being one of the faces of baseball, he still had a bit to “prove” entering 2022, with just two true full seasons on his career ledger. And though the Yankees’ $30.5 million AAV offer was certainly nothing to sneeze at, Judge knew he had a bonafide MVP campaign in the tank to end the discussion.

And he’s 1/3 of the way towards doing so.