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PoliticsRudy Giuliani

Rudy Giuliani fights to save his Yankees World Series rings from $148 million verdict

By
Michael R. Sisak
Michael R. Sisak
and
The Associated Press
The Associated Press
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By
Michael R. Sisak
Michael R. Sisak
and
The Associated Press
The Associated Press
Down Arrow Button Icon
January 2, 2025, 5:19 AM ET
Rudy Giuliani
Rudy Giuliani speaks with reporters as he departs a federal courthouse on Friday, May 19, 2023, in Washington. AP Photo/Patrick Semansky, File

NEW YORK (AP) — Ruth. Gehrig. DiMaggio. Mantle. Giuliani?

As Rudy Giuliani’s life gets stripped for parts to satisfy a $148 million defamation verdict, the former New York City mayor is fighting to keep one gleaming set of sports memorabilia in the family: Yankees World Series rings bestowed to him by the team’s late owner, George Steinbrenner.

A lifelong Bronx Bombers fan, Giuliani contends that the rings — bejeweled behemoths commemorating the team’s four championships in five years while he was mayor — now belong to his son, Andrew, and shouldn’t be given up.

In sworn testimony made public this week, ahead of a pair of key court dates, Giuliani described the 1996, 1998, 1999 and 2000 World Series rings as something of a family heirloom and Yankees good-luck charm.

He recounted how he and Andrew would each put one on for “a special Yankee occasion,” like the team’s last World Series win in 2009.

Giuliani testified that when Steinbrenner gave him the rings in 2002, he insisted on paying for them and told the owner, “These are for Andrew.” He said he then invited his son — a teenager at the time — to take one for himself while he held the others for safekeeping.

Realizing he wasn’t wearing them as much as the Yankees’ fortunes ebbed, Giuliani testified, he decided to give the rest to Andrew at a birthday party in 2018. He estimated that the rings, the same as the players received, were worth about $27,000.

“They are now yours,” Giuliani recalled saying. “These are your rings. I don’t know what I’m keeping them for. They belong to you.”

The ex-mayor took his swings at a Dec. 27 deposition, a week before the start of a courtroom doubleheader in a tug-of-war over assets sought by the two former Georgia election workers who sued him over his lies about them in the wake of President-elect Donald Trump’s 2020 election loss. A transcript was posted to the court docket on Monday.

Up first is Giuliani’s contempt hearing in Manhattan federal court Friday over what lawyers for the Georgia women say was his failure to turn over property in a timely fashion, such as his New York City apartment lease.

Then, on Jan. 16, Judge Lewis J. Liman will hold a trial to decide what happens not only to Giuliani’s World Series rings but also his condominium in Palm Beach, Florida. Giuliani claims the condo, estimated to be worth more than $3 million, is his primary residence and should be exempt.

For Giuliani, once heralded as “America’s Mayor” for his post-9/11 leadership, it’s the legal equivalent of two strikes, two out in the bottom of the ninth.

Lawyers for the former election workers, mother and daughter Ruby Freeman and Wandrea “Shaye” Moss, argue that Giuliani has engaged in a “consistent pattern of willful defiance” of court orders to turn over items.

In a Monday filing, lawyer Aaron Nathan said Giuliani’s compliance has been spotty, noting that while he finally surrendered a Mercedes previous owned by actor Lauren Bacall, he failed to provide the vehicle’s title.

After listing 26 watches in a bankruptcy filing, Giuliani now claims without explanation that 18 watches he turned over to Freeman and Moss are all he has, Nathan wrote. He added that Giuliani also claims not to know the whereabouts of a shirt signed by Joe DiMaggio or a photo signed by Reggie Jackson, both Yankees legends.

Freeman and Moss asked the judge in August to award them the World Series rings, but the judge demurred and scheduled a trial after Andrew Giuliani, now 38, said they belong to him.

Giuliani’s eight hours of deposition testimony offered a vivid portrait of a still-proud, combative and downtrodden man who has lost almost everything and remains convinced that it has been unjustly taken.

Recalling his days as a two-term Republican mayor, he boasted that he “cured” homelessness in the city while acknowledging that he is now rejected by most clubs he would like to join, except for two.

Questioned by Nathan, he spoke at length about the rings, his ties to Trump and the Yankees, and his dismay over his once-beloved Big Apple’s liberal politics — a factor he said drove him to relocate to Florida and register to vote there last May.

“Frankly, I wanted my vote to count,” Giuliani testified.

Asked why it was important to him to cast a vote for president, Giuliani replied: “Because I am a very, very strong supporter of Donald Trump, which is the reason why you are doing all of this to me.”

Before Trump, it was the Yankees. Giuliani, who saw them win 10 titles during his childhood and college years, regularly cheered the team as mayor, often sitting next to the dugout.

“I was a very ardent Yankee fan,” he testified. “When I was the mayor, I was described as New York’s No. 1 Yankee fan.”

After the team triumphed in 1996 to snap a 15-year drought, Steinbrenner thought “New York’s No. 1 Yankee fan” deserved a World Series ring — but Giuliani wasn’t having it.

“I didn’t think it was appropriate that a mayor get a ring,” Giuliani testified.

By the time he left office in 2002, the Yankees had three more championships.

At spring training that year in Tampa, Florida, Steinbrenner presented him with a plaque and three World Series rings, Giuliani testified, each engraved with his name.

“I was very touched and moved by that,” he said.

The Yankees also gave him the 1996 ring that he turned down, he said. He recalled showing all four rings to his son and telling him: “These are going to be yours.”

Each ring was bigger and more extravagant than the last, Giuliani testified, so much so that “you’d look crazy wearing it.”

Giuliani lamented that his rings didn’t bring the Yankees more success, noting their 2003 World Series loss to the Marlins and 2004 playoff collapse against the hated Red Sox.

“I stopped wearing them after the Yankees stopped winning because it was no longer working,” he said. “And then I wasn’t using them anymore.”

The Fortune 500 Innovation Forum will convene Fortune 500 executives, U.S. policy officials, top founders, and thought leaders to help define what’s next for the American economy, Nov. 16-17 in Detroit. Apply here.
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By Michael R. Sisak
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