What Boras’ Juan Soto ‘Mona Lisa’ pitch really means for Yankees

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At the recent general managers’ meetings, prominent sports agent Scott Boras delivered an insightful 48-minute analysis of Juan Soto’s market value, using his trademark wordplay to emphasize the player’s importance. Boras likened Soto’s impact on baseball to the Mona Lisa’s place in art, drawing comparisons to legends such as Willie Mays, Hank Aaron, and Ted Williams while projecting that Soto has 15 more years of peak performance ahead.

Boras underscored the financial weight of acquiring Soto, suggesting the investment could yield billions in revenue. He likened championship success to magic, positioning Soto as a key ingredient for any team aiming for a title.

““You have the Mona Lisa of the museum,”Soto’s agent said, You have the attraction. You also have a player who gives owners a better chance to win repeatedly. And when owners win repeatedly, revenues skyrocket.”You’re talking about a business opportunity where you can make literally billions of dollars by acquiring somebody. You can really see that owners, general managers, that they’re kind of called upon to be championship magicians. … It’s hard to do, to put together that magic of a championship run, but behind every great magician obviously is the magic Juan.”

His remarks came in response to questions about Soto potentially accepting a contract structure similar to Shohei Ohtani’s deal with the Los Angeles Dodgers, which includes significant deferrals. Financial analysis shows that Ohtani’s $700 million contract has a present value of $460.8 million, impacting MLB’s luxury tax by $46.08 million annually.

While the two players’ situations differ in terms of endorsement income, industry experts point out that Soto’s earnings from endorsements are currently estimated at about $3 million annually, far less than Ohtani’s reported $65 million. Analysts suggest Soto could see a boost in endorsements if he were to join a team like the Yankees, but his income would likely remain far below Ohtani’s, especially considering Ohtani’s unique popularity, particularly in Japan.

Financial analysts note that while the Dodgers have reaped benefits from Shohei Ohtani’s deferred contract structure in their free-agent pursuits, similar terms are unlikely for Juan Soto. During Wednesday’s MLB general managers’ meetings, agent Scott Boras highlighted that tax implications would take a backseat to the significant revenue Soto could generate for any team that acquires him.

Sources familiar with the situation reveal that while the New York Yankees are keen to retain Soto, they are open to exploring other options if a deal cannot be reached. Industry experts suggest that Yankees owner Hal Steinbrenner must present a substantial offer without expecting Boras to make significant concessions.

Reports indicate that Soto’s free agency decisions will not be driven solely by financial considerations. He is reportedly focused on joining an organization that is committed to long-term competitiveness—a factor that could play to the Yankees’ advantage. Despite failing to win a World Series since 2009, the Yankees consistently contend for playoff spots.

Boras has emphasized that the key to Soto’s decision will center on ownership commitment and a clear vision of sustained success, which will directly influence Soto’s enjoyment of the game. Sources say Boras maintains a positive working relationship with Steinbrenner, with frequent communication between the two.

“This is about owner commitment,” Boras said. “It’s about demonstrating to Juan Soto that his goals of winning and winning consistently are going to be met, because that’s what makes the game enjoyable for him.”

Industry insiders suggest that successful negotiations may require Steinbrenner’s direct involvement, much like his approach during Aaron Judge’s contract renewal two years ago. Yankees General Manager Brian Cashman has confirmed that the team has not yet received an opportunity to match competing offers for Soto. Baseball analysts believe that maintaining steady communication between Steinbrenner and Boras could give the Yankees a strategic edge as Soto’s free agency unfolds.

Sources close to the situation indicate that Juan Soto plans to meet with MLB team owners as part of a comprehensive effort to gauge his value across the league. Reports confirm that Yankees owner Hal Steinbrenner has already met with Soto to express the team’s interest in retaining him. While Soto has publicly stated his satisfaction with his time in New York and his comfort with the city, his agent makes it clear that all 30 MLB teams will be considered equally in the evaluation process.

“Juan knows who the Yankees are, and he’s certainly impressed and pleased,” the agent explained. “He went to the World Series with them, which is a tremendous accomplishment. But to truly understand what ownership thinks and what the Yankees’ future plan is, any player in his situation would want to hear about that. And with the respect he has for the New York Yankees, I know he’s going to want to be very thorough in this process.”

While Soto values the Yankees organization and their recent World Series appearance, his decision-making process will focus on detailed discussions regarding each team’s future strategic direction and ownership vision. Industry experts point out that Soto’s respect for the Yankees only reinforces his commitment to thoroughly evaluating all options.

Observers are drawing comparisons to Alex Rodriguez‘s historic contract negotiation 24 years ago, which set a record when he signed with the Texas Rangers. Both Rodriguez and Soto, in their mid-20s, reached superstar status while showing the potential for long-term greatness.

One key difference noted by baseball analysts is Soto’s championship pedigree and postseason performance. His clutch home run in Game 5 of the AL Championship Series against Cleveland and his impressive World Series numbers—four home runs, eight RBIs, and a .326 batting average in 12 games—further cement his value. 

Financial analysts suggest that Soto’s track record, combined with his younger age compared to Shohei Ohtani at the time of free agency, could position him to exceed Ohtani’s record-setting $700 million contract with the Los Angeles Dodgers. Experts emphasize Soto’s ability to generate significant team revenue through sustained on-field success, making a large contract offer a plausible outcome. 

With his proven success, championship experience, and youth on his side, Soto is expected to command one of the highest financial packages ever seen in MLB free agency.

The Yankees’ Soto strategy beyond Boras buzz

Baseball insiders say New York Yankees General Manager Brian Cashman faces significant challenges in reshaping the team’s roster this offseason, with several key contributors from the World Series roster heading into free agency, including two starting infielders, two outfielders, and three relievers.

Sources close to the situation indicate that Cashman’s priorities during the GM meetings center on retaining his right fielder and second-place hitter. Analysts predict a competitive bidding war for the player, with the Mets and Blue Jays already showing strong interest, and potential suitors including the Dodgers, Phillies, and Giants.

Market experts view the Yankees as leading contenders for Juan Soto, citing the success of his first season in New York. However, financial analysts warn that Soto’s contract demands could spark intense competition for his services or prompt some teams to seek more affordable alternatives.

Sources familiar with Soto’s situation suggest that the 26-year-old outfielder may be seeking a deal in the neighborhood of $600 million over 14 to 15 years. 

When asked about the possibility of meeting those financial demands, Cashman confirmed the Yankees’ interest in re-signing Soto but emphasized that the team is prepared to explore other options if needed.

“We certainly have an interest in retaining him and we’ll put our best foot forward there,” Cashman said. “But at the same time, that’ll either lead to us retaining him and signing him or we’ll be forced to go to a different direction if we can’t. Since (Soto) knows us, we are standing ready to meet with him if he feels necessary to meet with us as he understands the landscape of opportunities that now exists for himself. We are more than willing to meet as many times as he would like to meet. So we stand ready to do whatever.”

Reports from San Antonio reveal that initial discussions between Cashman and Soto’s agent, Scott Boras, began shortly after Cashman arrived at the GM meetings at the JW Marriott San Antonio Hill Country Resort & Spa. According to sources, Cashman sought to outline the framework for Soto’s free agency process, as the Yankees remain open to any level of engagement Soto feels necessary to thoroughly assess his options.

Sources indicate that while early discussions between Scott Boras and Yankees General Manager Brian Cashman did not delve into specific financial details, industry analysts predict that Juan Soto’s eventual contract could rank as the second-largest in baseball history, trailing only Shohei Ohtani’s $700 million, mostly deferred deal with the Los Angeles Dodgers.

Cashman shared that his approach to negotiations typically involves outlining what constitutes a legitimate opportunity for a player, which includes factors like financial thresholds, the appeal of the city, and a team’s competitiveness.

Reports following the Dodgers’ World Series win at Yankee Stadium highlight that despite Soto’s successful first season in New York—posting a .288 batting average, a career-high 41 home runs, 109 RBIs, and 129 walks across 157 games—there are no indications that the Yankees will receive preferential terms in negotiations.

Industry sources suggest that Soto’s free agency timeline will likely involve meetings with potential suitors over the next three to four weeks, with a decision potentially coming around the time of the Dallas Winter Meetings, scheduled for December 8-12.

Cashman outlined his strategy for initial talks, noting that the first stage of negotiations often involves gathering insights from agents to understand their client’s expectations. This helps lay the groundwork for deeper discussions and enables teams to adjust their offers based on market conditions.

Sources close to the negotiations note that these early-stage conversations are essential in shaping the direction of future talks, with teams using initial feedback to refine their proposals and strengthen their positions in the competitive bidding process.

Industry sources suggest that while Yankees General Manager Brian Cashman is handling initial talks regarding Juan Soto, more detailed negotiations are expected to involve direct discussions between managing general partner Hal Steinbrenner and Soto’s agent, Scott Boras. Cashman has acknowledged that deals of this magnitude require owner involvement, noting Steinbrenner’s established rapport with Boras and his active role in major organizational decisions. While the Yankees are eager to retain Soto, contingency plans are reportedly in place should the talks not materialize.

Financial analysts emphasize that teams vying for Soto are keen to avoid protracted negotiations that could stretch into 2025, as they aim to keep their options open for other free agents. Sources say Cashman has indicated the Yankees’ readiness to pivot to alternative targets if Soto’s decision-making process becomes delayed.

According to sources within the organization, the Yankees understand the importance of respecting elite players’ decision-making while also adhering to a strategic timeline. Cashman has stressed the need to avoid situations where lengthy waits hinder their ability to pursue other available talent.

Industry observers note similarities between Soto’s situation and Aaron Judge‘s free agency two years ago when the Yankees matched the Giants’ sizable offer with a $360 million, 10-year deal. Sources familiar with the negotiations suggest, like Judge, Soto’s preferences regarding his future remain unclear, adding an additional layer of uncertainty.

Baseball insiders argue that this ambiguity complicates the Yankees’ approach, as the organization remains flexible, preparing for multiple possible outcomes while continuing to shape their roster for the 2025 season.

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