New York Yankees' Aaron Judge hits a double during the fourth inning of a baseball game against the Baltimore Orioles Wednesday, May 25, 2022, in New York. (AP Photo/Frank Franklin II)

It’s almost as if The O’Jays wrote that song specifically about Aaron Judge in his final season before entering free agency. It should probably be Judge’s new walk-up song because, with each passing day, he’s adding more zeros to the contract he’ll receive this winter.

Judge is on an absolute tear, and not only does he have the New York Yankees positioned as the best team in baseball but he also is setting himself up for a massive payday in the offseason. Either by the Yankees or another club.

“Very few people get this opportunity to talk extension,” Judge told reporters in April after rejecting the Yankees’ seven-year, $213.5 million offer, news that general manager Brian Cashman revealed. “Me getting this opportunity is something special, and I appreciate the Yankees wanting to do that. But I don’t mind going into free agency. It is what it is.”

The three-time All-Star outfielder is having a career year, hitting .316 with a MLB-leading 21 home runs in just 52 games. He is on pace to break his career high of 52 homers (set in 2017 when he won American League Rookie of the Year) and finish with 60 HRs. No player has reached the 60-homer plateau since Sammy Sosa in 2001, although Yankees teammate Giancarlo Stanton came close in 2017 with 59.

While Judge is going to be a unique case this offseason for other factors, there is some precedent for superstar players excelling in their walk years before free agency. The two most recent examples are Bryce Harper and Manny Machado during the 2018 season.

Harper had a strong final campaign with the Nationals, slashing .249/.393/.496 with 34 homers, 100 RBIs and an MLB-best 130 walks. He landed a 13-year, $330 million contract with the Philadelphia Phillies that offseason.

Machado had an even better 2018 season, slashing .297/.367/.538 with 37 homers, 107 RBIs, 14 stolen bases and an All-Star appearance with the Baltimore Orioles before being acquired by the Los Angeles Dodgers at the trade deadline. He signed a 10-year, $300 million deal with the San Diego Padres that offseason.

Unlike Harper and Machado, who debuted at 19 and 20, respectively, and hit free agency after their age-25 seasons, Judge was a late bloomer. He made the big leagues as a 24-year-old and will enter the market at the age of 30.

Thirty years old is now an interesting age in baseball. After years of players getting monster contracts after their 30th birthday, those days have gone by the wayside, but it feels like Judge is going to be the exception to the rule.

A player comparable to Judge’s situation is third baseman Anthony Rendon in 2019. Rendon, then 29, had a monster year with career bests in average (.319), slugging percentage (.598), home runs (34) and RBIs (126) and finished third in National League MVP voting. He also hit .276/.344/.586 with two homers and eight RBIs to help the Nationals win the World Series. Even though he was entering his age-30 season, Rendon received a seven-year, $245 million deal from the Los Angeles Angels.

Cashing in on free agency
Player Age AVG/OPS HR RBI Contract
Bryce Harper 25 .249/.889 34 100 $330M, 13 years
Manny Machado 25 .297/.905 37 107 $300M, 10 years
Anthony Rendon 29 .319/1.010 34 126 $245M, 7 years
Aaron Judge 30 .313/1.059 21 42 TBD

Judge will be the premier player in this year’s free-agent market, and for a five-tool outfielder with 60-home-run potential, he’ll be looking at a hefty payday. Also, he has stayed healthy for the better part of two seasons — something that was an issue for him early in his career.

“At the end of this year, I’ll talk to 30 teams,” Judge said. “The Yankees will be one of those teams.”

But which team will pony up to make Judge a $300 million man, the amount he reportedly has been seeking?

The Yankees didn’t spend big this past offseason, and it’s easy to wonder if part of that decision was knowing they would need to pay their All-Star outfielder. But, like Judge said, there are now 29 other teams that will get a shot to sign him.

Realistically, there are only a handful of clubs, besides the Yankees, who could put that kind of money on the table. Two of those teams are the Dodgers and the New York Mets.

The Dodgers are the standard when it comes to spending money in baseball. But after giving Mookie Betts $365 million in 2020 and acquiring Freddie Freeman last offseason, the Dodgers would likely spend their money elsewhere. They also have their own free agent to try to retain with shortstop Trea Turner. But you can never count the Dodgers out of anything.

Judge landing with the Mets isn’t guaranteed. Starter Max Scherzer is on a high-AAV, short-term contract, and ace Jacob deGrom is also a free agent this winter. But owner Steve Cohen isn’t afraid of anything, including the new fourth tier of MLB's luxury tax threshold, which is nicknamed the “Cohen Tax.”

The Chicago Cubs are a wild card. They’re in the middle of a rebuild and are likely headed for another sell-off before the Aug. 2 trading deadline. But with only $105 million on the books for next season and nearly $130 million under the CBT, the Cubs have the money to make a big splash for Judge. But will owner Tom Ricketts reach that deep in his pockets to make it happen after the team has cut back significantly? Only time will tell.

Each offseason, one player offers a unique case study into what direction the industry is leaning. Judge is going to be that player. He decided to bet on himself, and if he remains healthy, that wager is going to make him a very happy man.

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