• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
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
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.”

Join us at the Fortune Workplace Innovation Summit May 19–20, 2026, in Atlanta. The next era of workplace innovation is here—and the old playbook is being rewritten. At this exclusive, high-energy event, the world’s most innovative leaders will convene to explore how AI, humanity, and strategy converge to redefine, again, the future of work. Register now.
About the Authors
By Michael R. Sisak
See full bioRight Arrow Button Icon
By The Associated Press
See full bioRight Arrow Button Icon

Latest in Politics

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Leadership
  • Success
  • Tech
  • Asia
  • Europe
  • Environment
  • Fortune Crypto
  • Health
  • Retail
  • Lifestyle
  • Politics
  • Newsletters
  • Magazine
  • Features
  • Commentary
  • Mpw
  • CEO Initiative
  • Conferences
  • Personal Finance
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map

© 2025 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.


Most Popular

placeholder alt text
Retail
Trump just declared December 26th a national holiday. What's open and closed?
By Dave SmithDecember 26, 2025
9 hours ago
placeholder alt text
Real Estate
Mark Zuckerberg gifted noise-canceling headphones to his Palo Alto neighbors because of the nonstop construction around his 11 homes
By Dave SmithDecember 25, 2025
1 day ago
placeholder alt text
Success
As millions of Gen Zers face unemployment, CEOs of Amazon, Walmart, and McDonald's say opportunity is still there—if you have the right mindset
By Preston ForeDecember 26, 2025
9 hours ago
placeholder alt text
Economy
Even if the Supreme Court rules Trump's global tariffs are illegal, refunds are unlikely because that would be 'very complicated,' Hassett says
By Jason MaDecember 21, 2025
5 days ago
placeholder alt text
Retail
Trump just declared Christmas Eve a national holiday. Here’s what’s open and closed
By Dave SmithDecember 24, 2025
2 days ago
placeholder alt text
Personal Finance
Trump turns government into giant debt collector with threat to garnish wages on millions of Americans in default on student loans
By Annie Ma and The Associated PressDecember 24, 2025
2 days ago

Latest in Politics

Politicsarms, weapons, and defense
Anduril founder Palmer Luckey is among the U.S. defense execs and companies sanctioned by China over arms sales to Taiwan
By The Associated PressDecember 26, 2025
1 minute ago
Trump
EconomyTariffs and trade
Trump’s tariffs actually slashed the deficit from a record $136.4 billion to less than half that. Here’s what else they did
By Wyatte Grantham-Philips, Paul Wiseman and The Associated PressDecember 26, 2025
2 hours ago
PoliticsU.S. military
U.S. launches strikes against Islamic State group in Nigeria after attacks target Christians
By Will Weissert and The Associated PressDecember 26, 2025
3 hours ago
tariffs
PoliticsTariffs and trade
53-year-old customs broker wants to ‘Make Trade Boring Again,’ saying you won’t believe how complex cheese is these days
By Matt Sedensky and The Associated PressDecember 24, 2025
2 days ago
nursing
LawPennsylvania
‘Never seen such heroism’: Christmas Eve bravery on display as rescuers rush into burning nursing home that rocked Pa. city for miles around
By Mingson Lau, Marc Levy, Mark Scolforo and The Associated PressDecember 24, 2025
2 days ago
charity
Arts & Entertainmentphilanthropy
Most Americans decide 2025 isn’t the year for charity, poll says
By James Pollard, Linley Sanders and The Associated PressDecember 24, 2025
2 days ago