Insiders foresee Yankees making a $350 million splash this offseason

A Yankees fan looking at the Yankee Stadium prior to the start of a game.
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Jeremiah Dobbs
Tuesday October 10, 2023

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The rebuilding exercise of the Yankees this offseason is likely to see a staggering $350 million being spent on free agents, according to Kirschner and Brendan Kuty of the Athletics.

He claims that the Yankees have decided to invest $200 million in Japanese pitcher Yoshinobu Yamamoto. Numerous teams have shown interest in Yamamoto, who is considered one of the top pitchers in the market. However, the Yankees have been pursuing him aggressively, with General Manager Brian Cashman and special advisor Omar Minaya even attending one of Yamamoto’s games, where he threw a no-hitter. Cashman’s presence signaled the Yankees’ strong determination to sign him.

While Yamamoto might not command a contract as substantial as that of Gerrit Cole, it’s not unreasonable to consider a team committing to him for a significant number of years. Yamamoto’s age suggests he could be a dependable rotation player for a decade or more. If the Yankees have concerns about their previous choice with Carlos Rodon following his challenging first season, they might decide to invest in Yamamoto. Alternatively, if they believe Rodon will make a strong comeback, adding Yamamoto to their roster would create an impressive top three in their starting rotation. 

The Yankees have made a move to sign Cody Bellinger, the second-best hitter available in free agency. While Ohtani from the Los Angeles Angels is the top player in free agency, the Yankees aren’t currently the leading contenders to secure his services. Before this, the Yankees had shown interest in Bellinger before the trade deadline, but the Chicago Cubs retained him.

Japanese athlete Yoshinobu Yamamoto

The Yankees are in need of an offensive boost, especially considering they ranked 24th in OPS this season. They currently have vacancies in both left field and center field. The center field position is open due to Jasson Domínguez‘s Tommy John surgery, which will keep him sidelined for at least half of the 2024 season.

Bellinger experienced a comeback season in 2023, bouncing back from two challenging years with the Los Angeles Dodgers. His performance led the Dodgers to non-tender him just a year ago. Now, teams need to determine whether Bellinger’s 2023 season is indicative of his future performance or if his struggles in 2021 and 2022 are still a concern. However, due to the Yankees’ need for improved hitters, they would decide to take a risk and sign Bellinger to a six-year, $150 million contract.

The Yankees look to sign the slugger of the Chicago Cubs, Cody Bellinger

Yankees make splashy trade with Cardinals

Before the trade deadline, the Yankees also talked to the St. Louis Cardinals, and they still appear to be potential trade partners. The Cardinals ended the season with the 26th-ranked starting pitching ERA, and their rotation outlook isn’t promising. They traded Jordan Montgomery to the Texas Rangers and Jack Flaherty to the Baltimore Orioles. Adam Wainwright is retiring, and Miles Mikolas had a rough year. In August, Cardinals president of baseball operations John Mozeliak stated that they need to acquire three starting pitchers in the offseason and plan to be very proactive in pursuing this goal.

The Yankees have a strong suit in their pitching depth. Michael King has solidified his place as a probable starter for 2024. Clarke Schmidt, Randy Vasquez, and Jhony Brito have shown promise in different capacities. Drew Thorpe earned the title of minor league pitcher of the year, and Chase Hampton is considered one of the organization’s top starting pitching prospects.

Brendan Donovan could be a suitable addition to the Yankees, addressing their needs. Donovan, a left-handed batter with a strong on-base percentage and low strikeout rate, had a .787 OPS in 95 games this season while showcasing versatility in multiple positions. His OPS would have ranked third on the Yankees, following Judge and Gleyber Torres. Given the Yankees’ need for more effective hitters in the upcoming season, Donovan appears to be a valuable solution.

Reports link Yankees to Cardinals' Brendan-Donovan
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However, acquiring Donovan might require a substantial offer, as he is a pre-arbitration player. To entice the Cardinals into considering a trade, the Yankees might need to include assets like Schmidt, Vásquez, and Clayton Beeter. Given the limited availability of impactful bats in the free-agent market, the Yankees could explore trade options to bolster their offensive lineup. 

Yankees may add more support staff

The Yankees could consider adding more familiar faces to their coaching staff. At the moment, it doesn’t seem like any of the current coaches are at risk of losing their jobs. The only uncertainty is hitting coach Sean Casey, who hasn’t committed to returning for a full season, although the Yankees are interested in retaining him.

Players have expressed their appreciation for Casey and assistant hitting coach Brad Wilkerson, who bring firsthand experience of the challenges in the major leagues. Given the positive impact of such mentors, it could be a smart move for the Yankees to seek out more of them. Last season, they brought in Yankees legend Andy Pettitte in a part-time role to advise pitchers. Additionally, the hiring of former Mets GM Omar Minaya and former San Francisco Giants GM Brian Sabean for front-office positions signaled a trend of involving experienced baseball veterans in decision-making roles.

Derek Jeter present a Monument Park replica to Tino Martinez.
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The Yankees might consider bringing in familiar faces like Nick Swisher, Tino Martinez, David Cone, Scott Brosius, or Willie Randolph to join their coaching staff. Swisher has been known for his energy, positivity, and experience, especially with the team’s minor leaguers in recent years. Tino Martinez, who coached in the Cape Cod League over the summer, could be another option. David Cone, who was previously interviewed for the pitching coach role, has remained connected to the game through his TV roles with ESPN and the YES Network. Scott Brosius, a beloved figure among the fan base, has coaching experience in college and with the Seattle Mariners. Willie Randolph, who lives nearby in New Jersey, might relish the opportunity to be involved with the game full-time again.

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