NEW YORK — The names Ruth, Gehrig, DiMaggio, Mantle, and now Giuliani may evoke a sense of pride among Yankees fans, but for Rudy Giuliani, the stakes have never been higher. As the former mayor of New York City grapples with a hefty $148 million defamation ruling against him, he finds himself in a legal battle to maintain possession of an impressive set of Yankees World Series rings, gifted to him by the late team owner, George Steinbrenner.
A devoted Yankees supporter, Giuliani argues that these rings, which celebrate the team’s four championships achieved during his tenure as mayor, rightfully belong to his son, Andrew. In newly released sworn testimony, Giuliani presented the rings not only as coveted memorabilia but also as cherished family heirlooms and symbols of good luck associated with the franchise’s glory years.
During his testimony, Giuliani recalled special moments shared with his son, donning the rings for significant Yankees events, particularly the team’s last championship win in 2009. Giuliani recounted that when Steinbrenner presented the rings to him in 2002, he insisted that they were meant for Andrew and encouraged him to select one ring to keep, while Giuliani would safeguard the others.
As the years passed and Giuliani noted a decline in the team’s performance, he decided to formally give the remaining rings to Andrew during a birthday celebration in 2018. He valued each ring, identical to those given to the players, at approximately $27,000 and stressed the sentimentality behind the exchange. “They are now yours,” he stated during the presentation. “These are your rings. I don’t know what I’m keeping them for. They belong to you.”
Giuliani’s deposition took place shortly before two crucial court hearings centered on assets claimed by Ruby Freeman and her daughter Wandrea “Shaye” Moss, former election workers suing him for defamation after he spread falsehoods about them following the 2020 presidential election. A transcript of the deposition was filed on Monday, revealing the mounting tensions over Giuliani’s compliance with court orders.
Leading off the courtroom showdown is a contempt hearing set for Friday in Manhattan federal court regarding Giuliani’s alleged failure to surrender certain properties, including his apartment rental in New York City. Following that, on January 16, Judge Lewis J. Liman will determine the fate not only of Giuliani’s World Series rings but also his Palm Beach condominium, which he claims is his primary residence, valued at over $3 million.
Once celebrated as “America’s Mayor” for his leadership during and after 9/11, Giuliani now faces significant challenges. His legal adversaries, Freeman and Moss, argue that Giuliani has persistently disregarded court mandates to provide necessary assets. In a recent filing, attorney Aaron Nathan pointed out Giuliani’s inconsistent compliance, noting that while he finally relinquished a Mercedes once owned by actress Lauren Bacall, he did not provide the vehicle’s title.
In a bankruptcy filing, Giuliani had listed 26 watches but later claimed—without much clarification—that he only had 18 remaining. Moreover, he expressed uncertainty about the location of signed memorabilia, including a shirt bearing Joe DiMaggio’s signature and a photograph autographed by Reggie Jackson, two icons beloved by Yankees fans.
Freeman and Moss previously sought the court’s approval to claim the World Series rings, but the judge postponed a ruling after Andrew Giuliani, now 38, asserted that the rings were rightfully his. Over eight hours of deposition, Giuliani painted a picture of a resilient figure, still fiercely proud and adamant that the upheaval in his life is unwarranted.
Reflecting on his tenure as a two-term Republican mayor, Giuliani boasted about his past accomplishments, including addressing homelessness, while lamenting his alienation from social circles he once occupied. He discussed the rings, his connections to Donald Trump, and shared his frustrations regarding the political shift in New York City, a reality he claimed ultimately influenced his decision to relocate to Florida and register to vote there.
“Honestly, I wanted my vote to count,” Giuliani shared. When pressed on the significance of participating in presidential elections, he emphasized his ardent support for Trump, suggesting it’s the reason behind his current woes.
Before aligning with Trump, Giuliani’s heart belonged to the Yankees. He watched the franchise capture 10 championships during his formative years, passionately rooting for them as mayor from seats near the dugout. Declaring himself “New York’s No. 1 Yankee fan,” he revealed that after the Yankees broke a 15-year title drought in 1996, Steinbrenner decided to honor him with a World Series ring. However, Giuliani initially felt it inappropriate for a mayor to receive such an honor.
As Yankees’ successes continued, when he departed from office in 2002, the team had secured three additional championships. Giuliani recounted a moment at the team’s spring training in Tampa when Steinbrenner awarded him a plaque along with three engraved World Series rings, expressing how moved he felt by the gesture. The Yankees also presented him with the 1996 championship ring he had initially declined, solidifying the deep bond between Giuliani and the franchise.
As he examined the four rings, Giuliani noted the stylistic evolution from one to the next, indicating that they were so extravagant that wearing them could appear eccentric. He expressed disappointment that these prized possessions failed to inspire the team to continued victory, reminiscing about their losses, including the 2003 World Series to the Florida Marlins and the 2004 playoff debacle against the bitter rival Red Sox. Giuliani remarked, “I stopped wearing them after the Yankees stopped winning because it was no longer working,” suggesting that the rings had become disconnected from their once-glorious legacy.
