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The MLB offseason hasn’t even started, but two of baseball’s biggest names are already fighting battles off the field. Dodgers star Shohei Ohtani faces a lawsuit tied to a failed Hawaii business venture, while Yankees captain Aaron Judge takes the opposite route—he’s the one filing.

Judge, 33, continues rehabbing an elbow strain after a disappointing playoff exit, but he’s also focused on protecting his money. Court filings in Hillsborough County show that Judge and his wife, Samantha, sued Florida interior designer Amanda Drew and her company, Drew Designs LLC, earlier this year. They accuse Drew of overcharging them by nearly $750,000 for work on their Tampa Bay mansion and New York City apartment.

The couple says Drew hooked them with promises of “special pricing” and a flat $10 per square foot rate. Instead, they discovered inflated prices—including a $33,000 couch they found selling elsewhere for about $18,000. Judge and his wife also accuse her of hiding receipts and exploiting their demanding schedules, believing they wouldn’t catch the inflated bills.

Drew denies the accusations and countersued the couple in March, claiming wrongful termination and unpaid invoices. So far, lawyers have issued more than 60 subpoenas to vendors and contractors involved in the project. The standoff shows no sign of ending quietly.

Judge faces this legal battle during a major transition in his career and personal life. He just wrapped up a 40-homer season that kept him in the AL MVP mix despite the Yankees’ postseason collapse. Now his offseason includes a legal fight in Florida and possible elbow surgery.

Ohtani’s Legal Trouble in Hawaii

While Judge sues to recover his money, Ohtani defends himself from investors. Reports say the Dodgers’ two-way star faces a lawsuit over a Hawaii real estate deal where investors claim he misled them about financial commitments. The litigation comes months after Ohtani’s interpreter became the center of a gambling scandal, dragging the superstar into unwanted headlines once again.

Both cases highlight the price of fame in modern baseball. Judge’s legal move aims to protect what he earned, while Ohtani’s defense forces him to explain how he got entangled in yet another off-field controversy. Each player sits on opposite sides of the courtroom—one holding the pen that files, the other holding the documents that defend.

Offseason of Rehab and Reflection

Judge now focuses on his elbow as the legal process unfolds. After the Yankees’ elimination, he told reporters he plans to “do some work on it” and hasn’t ruled out surgery. The flexor strain, which has limited his throwing since July, clearly impacted his postseason play.

He has about four months before spring training starts in February 2026—time to heal, rest, and prepare for another Yankees campaign. If he needs a break from court filings and rehab, he still owns a Tampa waterfront condo he bought in 2018 for $825,000. That property, at least, hasn’t caused any legal trouble.

While Ohtani’s Hawaii lawsuit keeps his name in controversy, Judge’s fight shows a different kind of headline—that of a player taking control, defending his family, and protecting his fortune, one lawsuit at a time.

Alvin Garcia Born in Puerto Rico, Alvin Garcia is a sports writer for Heavy.com who focuses on MLB. His work has appeared on FanSided, LWOS, NewsBreak, Athlon Sports, and Yardbarker, covering mostly MLB. More about Alvin Garcia