Yankees World Series Rings Remain Sticking Point in Giuliani Trial

Rudy Giuliani owns four Yankees World Series rings, one from each title that the MLB team won when he was mayor of New York City. Now he and his family are fighting to keep them.

Giuliani is currently facing a handful of legal challenges, including bankruptcy and a defamation case that he lost last year in federal court. In the latter, the former Donald Trump lawyer was ordered to pay $148 million to a pair of Georgia election workers who he claimed, without evidence, helped steal the 2020 presidential election. And the plaintiffs want his rings as part of that payment.  

Last month, Giuliani was ordered to turn over a number of assets toward that $148 million. They included his New York apartment, a 1980 Mercedes once owned by actress Lauren Bacall, a number of watches and some other sports memorabilia. Giuliani and his legal team have fought against turning over two items—his Florida condo and the Yankees rings. His son, Andrew, claimed in an October court filing that the rings had been gifted to him by his father in May of 2018, around 12:30 a.m. following the former mayor’s 74^th birthday party.

The issue of the rings’ ownership remains in limbo. In federal court this week, Giuliani’s new lawyer asked the judge to further delay his upcoming trial, currently scheduled for Jan. 16, to determine whether his client could keep the condo and the rings. The judge refused. Giuliani has already turned over 90% of the required assets, his lawyer said. “I can’t pay my bills,” Giuliani reportedly told the judge.

For many New Yorkers, the rings are a reminder of the close relationship between Giuliani and baseball’s most valuable franchise. He grew up a Yankees fan in Brooklyn—at a time when the Dodgers were still in town—but that tie became especially tight in the aftermath of the Sept. 11, 2001, terror attacks, when baseball became a rallying point for the city and its mayor. Giuliani frequently wore Yankees hats and jackets, was a mainstay at championship parades, and in the final weeks of his time at City Hall helped negotiate deals that led to the new Yankee Stadium. He wore one of his World Series rings during his failed 2008 presidential campaign.

In a court filing earlier this year, Giuliani listed the rings alongside a series of watches and other jewelry that he valued at $30,000 total. In response, a lawyer for the plaintiffs said in a filing that Giuliani had assigned “egregiously low values to his assets, including Yankee World Series rings,” according to Newsweek. Ken Goldin, founder of Goldin Auctions, said in an email that the four rings combined would likely be worth a combined $200,000 in a collectibles auction. That’s “a significant premium” over what they would fetch if they were previously owned by a lesser-known Yankees employee, he said.

The rings themselves have a long and somewhat murky history. A 2007 story in the Village Voice titled “The Yankees’ Clean-Up Man” looked into how and when Giuliani got them—questions that matter more than some fans might initially think. New York officials are prohibited by law from receiving gifts of significant monetary value from anyone doing business with the city. The Yankees, of course, do significant business with the city, and Giuliani never reported the rings as gifts with the city’s Conflict of Interest Board.  

A representative for the MLB team told the newspaper that Giuliani paid $16,000 total for them—$13,500 for the 1998, 1999 and 2000 rings paid in 2003, and $2,500 for his 1996 ring paid in 2004. All of those payments were after he left office, and the rep told the newspaper that it could be “reasonably deduced” that he didn’t receive the rings until then. Other sources, however, told the paper that he received the 1996 ring years earlier—in 1996 or 1997—while he was still in office. Each of those payments, regardless of timing, would have been well below the market value of the rings themselves, let alone the resale value of the items as collectibles.

Also of note, the Village Voice said the Yankees didn’t offer rings for sale to other non-team personnel during that run. (Representatives for Giuliani and the Yankees didn’t immediately respond requests for comment).

Regardless of the potential conflicts, Giuliani’s investment has paid off handsomely. A 1996 ring, 10-karat gold and made by Balfour, is currently for sale for $34,000. A 1999 version, 14-karat gold also made by Balfour, was recently listed at Sotheby’s with an estimate of $26,000-$35,000.

Championship rings remain among athletics’ most prized possessions, not least because modern ones are packed with gems. The Kansas City Chiefs’ 2024 rings reportedly cost $40,000 each, before factoring in symbolic value. In August, a pair of rings commemorating the Chiefs’ 2019 and 2022 triumphs each sold for more than $80,000 at Heritage Auctions.

A fraudulently acquired 2017 Patriots Super Bowl ring sold for more than $337,000 at auction in 2018, while New England owner Robert Kraft auctioned off his jewelry from Super Bowl LI for more than $1 million as a fundraiser during the COVID-19 pandemic. Bill Russell, Kareem Abdul-Jabbar, and Kobe Bryant rings have all hit the block in recent years, fueling the bauble bubble.

In recent years, teams have begun selling slightly cheaper versions to fans. Replica versions of rings have also been sold by official jeweler Jostens to Chiefs and Dodgers fans following championships in the last few years.