Rudy Giuliani, once celebrated as “America’s Mayor,” is now embroiled in a legal battle involving three New York Yankees World Series rings. Lawyers for Ruby Freeman and Wandrea “Shaye” Moss, two Georgia election workers awarded a $148 million defamation judgment against Giuliani, are demanding the rings as part of the payout.

The rings commemorate Yankees championships in 1996, 1999, and 2000 and were listed among Giuliani’s assets during a 2023 bankruptcy filing. However, Giuliani claims he gifted the rings to his son, Andrew Giuliani, at a 2018 birthday party. The lawyers argue there is no concrete evidence to support this claim and suggest the transfer may have occurred as recently as mid-2023, after Giuliani listed his Manhattan apartment for sale.

Court battle over Yankees memorabilia

The dispute will be decided in a trial set for January 16, which will also address the status of Giuliani’s Palm Beach condominium. The lawyers allege Giuliani has attempted to shield valuable Yankees memorabilia, including the rings, to avoid complying with court orders. They note Andrew Giuliani has not appraised or insured the rings, nor has he included them in any financial or estate planning.

If the court finds the rings were transferred in 2023, the lawyers argue the move should be deemed fraudulent, as it was likely intended to place the assets beyond the reach of creditors.

In a December deposition, Giuliani testified that Yankees owner George Steinbrenner personally gave him the rings in 2002, knowing they were intended for Andrew, then a teenager. Giuliani claimed he initially gave one ring to his son and held onto the remaining three before gifting them in 2018. However, the timeline is disputed, as Freeman and Moss’s legal team highlights inconsistencies in Andrew Giuliani’s testimony.

The rings, valued at approximately $27,000, are among the few assets Giuliani still claims ownership of, along with his Florida condominium, which he asserts is protected under state law as his primary residence.

Yankees legacy at the heart of legal battle

Beyond the World Series rings, other Yankees memorabilia has become a focal point in Giuliani’s financial troubles. He reportedly lost track of a jersey signed by Yankees legend Joe DiMaggio and a photo autographed by Reggie Jackson. These items, along with a Manhattan apartment and luxury vehicles, have been liquidated to satisfy mounting debts.

A spokesperson for Giuliani, Ted Goodman, criticized the pursuit of the Yankees memorabilia, stating, “They can fight to take Mayor Giuliani’s most cherished items, but they can never take away his extraordinary record of public service.”

As Giuliani faces increasing scrutiny, the legacy of the Yankees—a franchise known for its dominance and prestige—has taken center stage in this unfolding legal saga. Whether the rings will change hands remains to be seen, but their symbolic value continues to amplify the stakes in this high-profile case.