New York — Imagine being so passionate about your favorite baseball team that their World Series rings become a family treasure. That’s exactly what’s happening with Rudy Giuliani, the former mayor of New York City, and his collection of Yankees championship rings. Giuliani, who has always been a die-hard Yankees fan, is in the middle of a legal battle to keep these prized possessions in his family while dealing with a massive $148 million defamation judgment against him.
The story of these rings goes back to the Yankees’ golden era in the late 1990s and early 2000s when the team won four championships in five years. During that time, Yankees owner George Steinbrenner gave Giuliani these rings to celebrate the victories. Giuliani says the rings aren’t just fancy jewelry—they’re family heirlooms. He insists that he always intended for them to go to his son, Andrew, who was just a teenager when the first ring was gifted.
In sworn testimony, Giuliani recounted how Steinbrenner presented him with the rings, and he insisted on paying for them, telling Steinbrenner they were meant for Andrew. Over the years, Giuliani and Andrew would wear the rings on special occasions, like when the Yankees won their last World Series in 2009. Eventually, Giuliani handed them over to Andrew during his birthday in 2018, saying, “They’re yours now.”
But the rings are now part of a heated legal fight. Two former Georgia election workers, Ruby Freeman and Wandrea “Shaye” Moss, who sued Giuliani over his false claims about their involvement in the 2020 election, want the rings as part of the settlement. They’ve accused Giuliani of dragging his feet in handing over assets, which include not just the rings but also a condo in Palm Beach, Florida, and even a Mercedes once owned by actor Lauren Bacall.
In court filings, Freeman and Moss’s lawyer pointed out inconsistencies in Giuliani’s financial disclosures. For example, Giuliani listed 26 watches in a bankruptcy filing but later turned over just 18. He also claims he doesn’t know the whereabouts of other Yankees memorabilia, like a Joe DiMaggio-signed shirt or a photo signed by Reggie Jackson.
A trial scheduled for January 16 will decide the fate of the World Series rings and the condo, which Giuliani says is his primary residence and should be exempt. In the meantime, a contempt hearing in Manhattan federal court will address whether Giuliani failed to comply with court orders to provide other property details.
Giuliani, who once earned the nickname “America’s Mayor” for his leadership after the 9/11 attacks, seems to have fallen from grace. During his deposition, he spoke candidly about how he feels wronged and how his life has unraveled. He also shared fond memories of his time as mayor, often sitting near the Yankees’ dugout during games and being dubbed “New York’s No. 1 Yankee fan.”
The story of the rings reflects Giuliani’s deep connection to the Yankees. The 1996 ring, which he initially refused because he didn’t think it was appropriate for a mayor to accept such a gift, was eventually given to him along with three others after he left office in 2002. Each ring, engraved with his name, became more extravagant than the last—so much so that Giuliani joked about how odd it would look to wear them all at once.
Giuliani even admitted to thinking the rings brought good luck to the Yankees. But after the team’s disappointing performances in the 2003 World Series and the infamous 2004 playoff collapse against the Boston Red Sox, he stopped wearing them altogether. “I wasn’t using them anymore,” he said, adding a touch of wistfulness to his testimony.
Now, as he fights to keep these sentimental pieces in his family, Giuliani is also fighting to keep his legacy intact. For him, the rings are more than just symbols of a sports dynasty—they’re a reminder of a time when both he and the Yankees were on top of the world. Whether they’ll stay in the Giuliani family or become part of the legal fallout remains to be seen.
