The New York Yankees postseason will start on Saturday, October 5, against the winner of the Kansas City Royals and Baltimore Orioles series. An exciting time for the fan base and players, the Yankees’ pressure to win in 2024 could be bigger than ever due to Juan Soto’s pending free agency.

Not only would winning a World Series be a strong selling point to Soto, but there’s a chance that he won’t be on the roster next year, and replacing him is nearly impossible.

The biggest question surrounding Soto continues to be his potential contract. Many, including Michael Ginnitti of Spotrac, believe it could reach the $500-plus million mark.

Ginnitti predicted Soto would land a 14-year, $530 million deal, totaling about $37.85 million per season.

“Everyone said the Soto/Yankees marriage would be a dream walk-year scenario for Soto,” Ginnitti wrote in August. “Everyone was right. There will be multiple teams attempting to lock in the 2nd largest contract in MLB history.”

Soto Met With Yankees Owner Hal Steinbrenner in July

Brendan Kuty of The Athletic reported that members of the New York Yankees front office, including owner Hal Steinbrenner, have had conversations with Soto.

The most recent conversation occurred in July, but according to Kuty, Soto declined to discuss the specifics of their conversation.

“If the New York Yankees have any advantage heading into the sweepstakes to sign star Juan Soto, it’ll be familiarity,” Kuty wrote on September 27. “It’s why they have spent their only guaranteed season with the coveted free-agent-to-be trying to learn about what makes him tick.

“Part of that intelligence-gathering mission included a private meeting between Soto and one of the people who may shape the outcome of winter’s most prominent free agent pursuit: Yankees owner Hal Steinbrenner.”

Kuty added that, despite Soto, Steinbrenner, and Soto’s agent Scott Boras declining to comment, a source familiar with the situation said the conversation was about Soto’s experience.

“But, according to a person with knowledge of the conversation, much of the talk was focused on Soto’s experience so far with the Yankees,” Kuty wrote. “How has he enjoyed his time with the team? What could the Yankees do to enhance the experience of playing for them from the standpoint of a player new to the team?”

Soto’s Comments on His Pending Free Agency

Soto has made comments about his upcoming free agency throughout the year, and so has his agent.

According to Kuty, the left-handed slugger spoke about wanting to be in the New York Yankees history books and more but acknowledged that he might not be back in 2025.

“I think anybody would want to be in the history books for the Yankees,” Soto said. “I’ve been trying all year to be part of it — at least even if it’s for one year. I’m trying my best to be around those books with the World Series champions. But we’ll see. We will see how it’s going to be. At the end of the day, you never know if you’re going to be there.”

25-years-old, Soto has had another career campaign, posting a .288/.419/.569 slash line with 41 home runs and a 178 OPS+. Those types of numbers could warrant a $500 million contract.