New York Yankees captain Aaron Judge has kept close tabs on teammate Juan Soto during their first season together. 

As the two stars prepare to play in the World Series against the Los Angeles Dodgers, Judge knows this could be the last series he plays alongside the young phenom. Soto will hit free agency this winter and could command the largest contract in MLB history, outside of Shohei Ohtani's $700 million deal. 

The Yankees won't be the only bidder at the table for Soto, who is sure to have plenty of options from other teams. 

But Judge believes Soto will make "the right decision," whatever that means to them. 

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Juan Soto celebrating ALCS

Juan Soto of the New York Yankees celebrates after beating the Cleveland Guardians, 5-2, in 10 innings to win Game 5 of the American League Championship Series at Progressive Field Oct. 19, 2024, in Cleveland. (Nick Cammett/Getty Images)

"When the time comes, when this is all over, he'll make the right decision," Judge told reporters Thursday. 

Judge was in a similar position with the Yankees just two years ago. After clubbing an American League record 62 home runs and winning his first MVP award, Judge entered free agency for the first time in his career. 

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Judge's negotiation with the Yankees in December 2022 was a time of confusion and anxiety for Yankees fans because his decision was shrouded in mystery. It culminated in an infamous false report from New York Post MLB insider Joel Sherman that Judge "appeared headed" to the San Francisco Giants

Judge reportedly received a 10-year, $400 million offer from the Padres that winter but gave the Yankees a chance to bolster their offer. In a last-minute phone call with owner Hal Steinbrenner, Judge negotiated a nine-year, $360 million deal with the Yankees, taking one year and $40 million less to stay in pinstripes. 

Juan Soto hits ball

New York Yankees outfielder Juan Soto hits a solo home run during the third inning against the Cleveland Guardians in Game 1 of the 2024 ALCS at Yankee Stadium. (Brad Penner/Imagn Images)

Soto set career highs this year with 41 home runs and 128 runs scored and produced his signature Yankee moment with a game-winning three-run homer in the 10th inning of Game 5 of the ALCS against the Cleveland Guardians Saturday. 

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Afterward, multiple teammates pleaded publicly with Soto to stay with the Yankees. 

"We need him to stay. He's going to stay. We need to bring it home, then we'll bring him home also," ALCS MVP Giancarlo Stanton said after the game.

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"Pay my guy! Pay Juan Soto! $700 million!" said infielder Jazz Chisholm, who joined the team at the trade deadline after competing against Soto in the National League. 

Yankees fans who stuck around in Cleveland after the game even chanted "Re-sign Soto!"

Soto is represented by MLB super agent Scott Boras, who has a notorious history of squeezing teams for every penny in negotiations. 

But Steinbrenner might not go for a $700 million demand, even if Chisholm thinks it's worth it. 

Hal Steinbrenner speaks to the media

Yankees principal owner Hal Steinbrenner speaks during a press conference at Yankee Stadium Dec. 21, 2022, in the Bronx, N.Y.  (Dustin Satloff/Getty Images)

"I’m gonna be honest. Payrolls at the levels we’re at right now are simply not sustainable for us financially,’’ Steinbrenner told the New York Post in May. "It wouldn’t be sustainable for the vast majority of ownership [groups], given the luxury tax we have to pay.

"I don’t believe I should have a $300 million payroll to win a championship."

With other wealthy bidders out there gunning for Soto this winter and a Yankees owner reluctant to increase his payroll, the star slugger may have to decide on taking less money to stay with the Yankees as Judge did. 

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