Rudy Giuliani, once celebrated as “America’s Mayor,” is back in the headlines, but not for his political career. This time, he’s facing a trial over the ownership of some surprising assets: his Florida condo and a set of New York Yankees World Series rings.
The situation raises eyebrows, not just because of the legal battle, but because many people wonder: why does Giuliani even have these rings in the first place?
A Mayor with a Passion for Baseball
Giuliani is well-known as a lifelong Yankees superfan. During his time as mayor of New York City, he was a frequent presence at Yankee Stadium, cheering on the team during their late-1990s dynasty. After leaving office, Giuliani purchased four World Series rings commemorating the Yankees’ championship victories in 1996, 1998, 1999, and 2000.
These rings, engraved with his name, were not gifted by the team but were bought by Giuliani himself. While it’s not unheard of for high-profile fans to acquire memorabilia, owning multiple championship rings is unusual. Most people associate such rings with players, coaches, and team staff, not politicians.
The Yankees themselves aren’t exactly clear from scandals, having faced their share of controversies over the years, from allegations of sign-stealing to disputes over player contracts. While the team has built a reputation as one of baseball’s most successful franchises, many feel that they are overrated and its connection to high-profile fans like Giuliani adds another layer of intrigue.
The Legal Battle Over the Rings
Now, these prized possessions are at the center of a courtroom drama. Giuliani, who has faced mounting legal and financial troubles, was ordered to pay $146 million in damages to Georgia election workers Ruby Freeman and Wandrea “Shaye” Moss. They successfully sued him for defamation after he falsely accused them of election fraud in 2020.
To satisfy the judgment, Freeman and Moss are seeking some of Giuliani’s most valuable assets, including three of his World Series rings. Giuliani claims he gave the rings to his son, Andrew Giuliani, as a gift in 2018. However, Freeman and Moss’ lawyers argue that this gift is questionable, pointing out that Giuliani continued to list the rings as his property in legal filings as recently as 2023.
Related: The 30 Best Moments from World Series History
A Trial Full of Twists
The trial has revealed conflicting accounts. Andrew Giuliani says his father gave him the rings in 2018 but didn’t physically hand them over until 2023. Rudy Giuliani, on the other hand, says he forgot about the gift until his son reminded him. Adding to the confusion, Giuliani was photographed wearing the rings during the years they were supposedly no longer his.
While the trial may determine who legally owns the rings, it underscores the unusual nature of the situation. Giuliani’s connection to the Yankees as a fan is well-known, but owning multiple World Series rings — typically reserved for players and staff — feels out of place for a politician.
Now, these symbols of a storied baseball dynasty have become entangled in a high-stakes legal battle, adding another layer of complexity to Giuliani’s already controversial legacy.
