Aaron Judge’s Big Gamble Forces An Historic Payout From The New York Yankees

Roughly three and a half hours before he embarked on his historic 62-homer season, Aaron Judge found himself answering questions about a new contract not getting done and when he spoke for those few minutes there was no way the slugger could know he was about to embark on an history making journey.

Shortly after Judge’s brief comments on the matter, GM Brian Cashman pulled the unorthodox move of actually telling the sizable audience in the Yankee Stadium interview room the exact amount of the offer, rationalizing it was going to get leaked out by someone at some point maybe even that very day and maybe even before the first pitch of the new season was thrown.

Nearly eight months after Cashman’s public admission of a $213.5 million offer, Judge will be on the way to an impressive $360 million deal spanning nine years with the Yankees, making it the biggest and successful gambles a player ever made on himself.

“He’s an amazing player and an amazing person that certainly has the respect of everyone in that room,” manager Aaron Boone said after experiencing the angst of a possible lineup without Judge.

In the world saturated by gambling and gambling advertisements, more often than not the house always wins, and the bettor loses. This time, Judge’s gamble made the house (the Yankees) payout a winning ticket of $146.5 million extra to account for the difference from the offer to the newly signed deal that is the highest contract for any free agent for now.

And with every one of his 62 homers, the imaginary sound was cash registers ringing.

Judge and his agents heard them with the price of his next contract going up and the Yankees heard them at every sale of anything related to Judge, especially during the final weeks when Judge reached 60, tied Roger Maris and broke the mark.

“Clearly I’ve never had to negotiate and try to retain somebody that just broke Roger Maris’ American League home run record,” Cashman said to reporters at the winter meetings in San Diego.

Back in April after the rejection of the initial offer, there never seemed to be any doubt the Yankees would need to up the ante regardless of whether the season ended with a championship or a loss in an earlier postseason round. It was just a matter of by how much and the Yankees found their answer each time Judge hit a ball over a fence and rounded the bases.

The signs seemed pointed in the right direction for Judge’s return, with managing general partner Hal Steinbrenner saying at last month’s owner’s meetings at MLB headquarters he had met with Judge, making those comments at about the team close friend Anthony Rizzo earned a slight raise in his new contract with the Yankees.

Regardless of what the opinion is about the back end of the deal and the prevailing concept of those deals experiencing rough endings, retaining their superstar and likely biggest source of merchandising revenue was a no-brainer for the Yankees, who experienced what seemed like an unprecedented amount of ill-will from fans for a team that reached 99 wins and the ALCS.

The angst of will or he won’t he started after the Yankees couldn’t get it done within the exclusive negotiating window, though there was not even a 52 percent chance of that happening.

Judge was going to explore all that free agency had to offer and that included bids by his hometown team the San Francisco Giants and apparent last-minute meeting with the Padres, who lost out on Trea Turner despite reportedly offering the shortstop $42 million more than his deal with the Phillies.

Then came a moment that seemed to throw people off the trail as Time Magazine named him their “Sports Person of the Year” with an accompanying story, whose main aggregated quote seemed to highlight Judge being peeved about Cashman telling the media and subsequent twitter followers of the media about the offer a few hours before Judge took the first of his 570 at-bats in breaking the AL-record.

It seemed when those comments were released there was a chance of Judge leaving the Yankees and perhaps that spurred Steinbrenner into action. Steinbrenner got the deal done long-distance style by speaking to Judge from Italy after Cashman texted all parties Tuesday night.

And eventually when word trickled out about Judge’s impending contract early enough on the East Coast that morning radio shows were talking about it, the bottom line was that Judge cashed in a way few gamblers actually do while being saturated with gambling ads and content.

He cashed in because not only did he produce one of the most spectacular seasons in a contract year in any sport because with each homer the leverage increased because the contingency plan with the outfielder was nowhere near as appealing and if it cost $360 million so be it for the Yankees, who own the distinction of possessing a trio of $300 million contracts.

“(Hal Steinbrenner) stated he would do everything in his power to try to make sure that we could retain Aaron Judge,” Cashman told reporters Wednesday in San Diego “Rest assured that he is putting his money where his mouth is in those efforts.”

And now that the head of the Yankee house delivered the money to Judge, the Yankees can move on to the rest of their offseason, improving a team that fell short in its World Series of bust expectations and add to a clubhouse of players who all advocated for Judge to get his big payday.