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How to Negotiate the Biggest Raise Ever and Earn an Extra $146 million in Nine Months

a cartoon depicting Aaron Judge's life

What can you learn from the guy who just negotiated a $140+ million raise? Everyone knows I love baseball, and this story was too good to pass up!  

Aaron Judge, the New York Yankee with a knack for hitting the ball really, really hard, has accomplished the feat of negotiating for himself one of the biggest raises ever in baseball history, with reports indicating that his new contract will be for nine years and $360 million. Considering that Judge turned down the Yankees’ original offer of seven years for $213.5 million, and entered the 2022 season gambling that he’d shine during his free agency, it was a heck of a bet he made on himself–a bet that paid off big time!

There are lessons to be learned from Judge, beyond the obvious “be one of the best baseball players in the world” and “break Roger Maris’ American League record with 62 home runs.” In fact, these lessons can help anyone–whether you’re an outfielder for the Yankees on the tail end of their contract, or simply someone hungry for a winning negotiation strategy. 

Batter up! Because it’s time for six lessons why Judge got this massive salary increase, and how they’re good advice for anyone in a negotiation. 

  1. Bet on Yourself 

Judge averages about 650 plate appearances a year, so he will be paid about $61,000 per plate appearance. In addition, the Yankees play 162 games, which means he will be paid around $246,000 per game… whether he plays or not.

How did he get to this enviable position in baseball? 

In April, the Yankees offered him a $213.5 million contract extension. That’s a lot of money, especially for a 30-year-old player staring down the daunting abyss of free agency and the back half of a career. Signing that contract would’ve been a safe move, because if he got injured during this past season, or simply had a bad year–both of which are always possibilities in professional sports–it would cost him all the money he could’ve earned.

But what did Judge do? He took the riskier path, turning down financial security and betting on himself. 

It was a huge bet that, ultimately, we now know will have paid off.

Therein lies the first lesson: bet on yourself!

“Aaron Judge is cashing in on the bet he placed on himself last spring.” – The New York Times 

  1. Really Perform Under Pressure 

At 6 feet, 7 inches, Judge has always been an impressive player. The Yankees scooped him up as a first-round pick in 2013, and he earned the American League’s Rookie of the Year Award in 2017. And for all his abilities as a slugger, he’s a pretty darn good outfielder, too, with Gold Glove and Wilson Defensive Player of the Year awards.

Going into the 2022 season, Judge was under a lot of pressure to perform. Sure, he had the skills and the track record, but without the safety net of a contract, could he deliver the goods with the weight of his future on his shoulders? More importantly, he’s also had a history of injuries that could’ve put his entire payday at risk. Judge needed to perform, but he also needed to stay healthy.

Aaron Judge hitting a baseball
The New York Yankees’ offer to Judge is a record-breaker–much like Judge himself!

The answer to the performance question came in the form of 62 home runs and 131 RBIs, and a .311 batting average that was just five points away from earning him the Triple Crown. Though the Yankees lost the American League Championship Series to the Houston Astros, Judge captivated fans chasing–and eventually breaking–Maris’ record. For his efforts, Judge won the league’s Most Value Player Award.    

Many people crumble under pressure. Not Judge. He did exactly what he needed to do, which is to perform when he needed it most. Judge bet on himself and completely crushed it!

  1. Wait and Create a Competition 

When Judge’s final arbitration contract was in its home stretch, the Yankees made him an offer that, from their perspective, was fair market value. As this was prior to Judge’s fantastic 2022 season, the offer was a valid one considering the slugger’s accomplishments and track record at the time. Length of contract was one of the biggest sticking points, with the Yankees in April of 2022 wanting to only go to seven more years for a 30-year-old player.

(Not that a Major League Baseball player would ever use them, but here’s a breakdown of important networking sites for your job search, courtesy of Bold.)

But Judge saw things differently, and to shake up any notions of what market value would be, he played his final arbitration year out and entered free agency. He entertained offers from other franchises, like the San Francisco Giants and the San Diego Padres. 

Did Judge seriously consider signing with these other teams? We don’t know for certain, and he has said his Yankee legacy mattered.  Yet, he negotiated with them, and as a native Californian, the possibility existed that either one could be his new team. This competition for his services was enough to force the Yankees to rethink his market value and bump up their original offer.

Clearly, creating competition is essential for shaking up market value and negotiations.

  1. Don’t Rush

 Nine months can be an eternity if you’re a free agent with a murky future, but if that time in limbo is also an opportunity you can use to prove your true worth, then it’s time well spent.

Don’t rush. Don’t rush into rash, fear-driven decisions, and don’t rush headlong into a future you don’t want. If time is what you need to showcase your abilities, shake up the market’s perception of you and build negotiating leverage, then take the time you need to shine. Time is on your side. Even during the free agency period, it seemed every day Judge waited, the higher the offers were going.  

(Do you prefer football over baseball? If so, here’s a Bold story for you.)

  1. Understand the Employer’s Needs 

Judge knew his potential and what he was capable of, but perhaps what was even more valuable was his understanding of what his employer needed.

With fewer World Series victories, the franchise needs superstars and well-liked players. After all, even if the team isn’t winning championships, fans will tune in just to watch their favorite athletes play. And these iconic players don’t just drive fan interest–they also have a hand in ticket sales, TV ratings and drawing advertisers.

In short, the Yankees need a new face and a new star. 

A Yankees sign amidst some memorabilia
The Yankees’ offer to Judge is a contractual grand slam–how did he do it?

Judge understood his employer’s needs and used it to his advantage.

  1. Bite Your Tongue and Keep Focused on the Prize 

When he declined the Yankees’ offer in April, the team released the details of the failed negotiations to the public–a move that definitely rubbed Judge the wrong way.

But instead of voicing any grievances, Judge bit his tongue, kept his mouth shut, and went out and performed. He took the high road, and wisely did not burn any bridges.

How different would things be if Judge had made his displeasure known and aired his grievances? We’ll never know, but we do know that biting his tongue and focusing on the prize resulted in the biggest offer to a free agent in history!

In response to the news of the Yankees’ historical offer, Jonathan Jones of CBS Sports wrote, “The moral of the Aaron Judge story for everyone is to always bet on yourself if you happen to have one-in-a billion talent.” But that’s not true.

Most people do not think of athletes as employees, and put the negotiations and contracting of players into a unique set. Yet at the end of the day, the Judge negotiation and employment contract has many valuable lessons.  When you are having your next negotiation, you might want to say “Batter Up” and apply some of Judge’s Bold, winning tactics!


Ed Kopko, CEO and Publisher of Bold Business

Edward Kopko
CEO & Publisher
Ed Kopko is’s CEO and Publisher. He has a passion for business, economics and media. A serial entrepreneur, Ed has launched Bold Business to help broadcast the great accomplishments that come from business and entrepreneurial activity. He believes the very real and amazing Bold Impacts that these activities have created also make a micro economic case for trade and commerce. Ed’s previous media experience was as CEO, Publisher and Owner of Chief Executive Magazine and its related media activities. He has been published in many media venues including the Wall St. Journal, Detroit Free Press and He has also been a sought after commentator and appeared numerous times on CNBC, MSNBC, Fox News and other media outlets.

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