Rudy Giuliani's Journey Of Losses: World Series Rings, Contempt

UPDATED: 11 a.m. ET, Jan. 8, 2025 Originally published April 28, 2021 The consequences of showing blind loyalty to Donald Trump continue to reveal themselves in the most amazing of ways. Rudy Giuliani‘s journey of losses since he tried and failed to illegally overturn the 2020 election results by defaming Black women poll workers is showing no signs of ending anytime soon. That truth was resoundingly punctuated this week after Giuliani was first found in contempt of court for evading payments in a $148 million defamation judgment before learning that the World Series rings he gifted his son could be seized as part of the ongoing case. The Associated Press reported that Judge Lewis J. Liman ruled on Monday Giuliani “willfully violated a clear and unambiguous order of this court” by failing to provide evidence that he shouldn’t have to turn over his condo in Florida. That prompted Liman to find Giuliani in contempt, one of wheat could be more sanctions to come.

Love NewsOne? Get more! Join the NewsOne Newsletter

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Subscribe

We care about your data. See our privacy policy.

On Tuesday, lawyers filed a motion demanding that the World Series rings from the New York Yankees in 1996, 1999 and 2000 should also be forfeited and turned over as part of the massive judgment’s collection of assets from Giuliani, who said without any proof that he gave them to his son. A trial to determine whether the condo and the World Series rings will be seized has been set for next week on Jan. 16. MORE: Video Shows ‘Drunk’ Rudy Giuliani Slurring Words In 9/11 Speech Weeks After Saying He’s ‘Not An Alcoholic’  It’s been a rough go for the lawyer formerly known as “America’s Mayor” who was previously hired to defend Trump in the aftermath of the 2020 election and espoused debunked conspiracy theories about non-existent election fraud that helped fuel the anti-government sentiment responsible for the Capitol riots. For example, in addition to menacing Black women election workers, Giuliani made false claims about Democrats rigging the election with malfunctioning voting machines. Since being named as a part of the Fulton County district attorney’s investigation into election interference, Giuliani has been the recipient of a seemingly neverending string of losses. In 2022, a disciplinary panel recommended Giuliani’s disbarment stemming from his “frivolous” and “destructive” defense of “the big lie” that President Joe Biden didn’t legitimately win the 2020 election. “[Giuliani] claimed massive election fraud but had no evidence of it,” the Board on Professional Responsibility, part of the D.C. Bar, wrote in its recommendation. “By prosecuting that destructive case Mr. Giuliani, a sworn officer of the Court, forfeited his right to practice law.” Aside from the latest trouble Giuliani has found himself in, separate investigators previously inquired for two years into whether he had any illegal dealings lobbying Ukraine officials in 2019 for information regarding Trump’s adversaries including Biden and his son, Hunter Biden. The feds were also looking into whether Giuliani attempted to undermine the former ambassador to Ukraine, Marie L. Yovanovitch. Prosecutors eventually charged his Ukrainian associates, Lev Parnas and Igor Fruman, in 2019. Yet and still, instances like finally admitting he made false claims about the 2020 election only draw further attention to Giuliani’s steady public fall from grace, much of which was already very apparent to Black communities who were privy to his inner workings after five decades of languishing in the political spotlight. At the height of his praise, Giuliani was heralded for helping to take down New York City’s mafia bosses in the ’80s and then successfully won his bid for mayor in the 1990s. After the September 11 attacks, Giuliani was considered “America’s Mayor,” only to morph into an obstructer of democracy as one of the main lie-spreaders around Trump’s loss in the 2020 presidential election. From spreading racist conspiracy theories to upholding harmful policies like stop-and-frisk in New York City, Giuliani is seemingly headed toward a different hall of fame amid desperate and disingenuous attempts at revisionist histories to save him from his continued, spiraling downfall. Keep reading to see the fine print details of Rudy Giuliani’s ongoing journey of spectacular Ls.

1. Defense Attorneys Want Nothing To Do With Rudy Giuliani’s Case

On Dec. 9, 2024, Rudy Giuliani blamed a federal judge for defense lawyers not wanting anything to do with his case.

The Atlanta Journal-Constitution reported that Giuliani “told U.S. District Judge Beryl Howell that four lawyers refused to accept him as a client because they think the judge is “unreasonable and biased about Trump related matters.” the former New York City mayor told U.S. District Judge Beryl Howell that four lawyers refused to accept him as a client because they think the judge is “unreasonable and biased about Trump related matters.”

More from the Atlanta Journal-Constitution:

One attorney, Giuliani wrote, called his case “a foregone conclusion” and a “no-win proposition.”

“Among other numerous reasons your handling of the (Jan. 6) cases is considered by many to be the most unnecessarily harsh,” Giuliani told Howell.

He told the judge those attorneys consider her to be “ideological rather than logical.”

In declining to represent him, Giuliani said the attorneys cited objections from their firms about the effect the case may have on their practice. This comes after two of Giuliani’s lawyers asked to be removed from the case last month, citing disagreements with their client.

2. ‘I Can’t Pay My Bills’

In November 2024, Rudy Giuliani lashed out at a judge who ordered the disgraced former NYC mayor to pay his mammoth debt to the Black women he was found guilty of defaming.

3. Judge Orders Rudy Giuliani To Transfer Personal Property To Election Workers He Defamed

A federal judge ordered Giuliani to forfeit his most valuable assets as a Black mother and her daughter who he defamed over the 2020 election begin collecting on a mammoth judgment they were awarded as a result. Those assets include “personal property ‘including cash accounts, jewelry and valuables, a legal claim for unpaid attorneys’ fees, and his interest in his Madison Avenue co-op apartment to a receivership’ within seven days,” NBC News reported.

The New York Times previously reported that Giuliani — who “owes about 20 people and businesses about $153 million, including $148 million to the two election workers, Ruby Freeman and Shaye Moss” — hasn’t produced a repayment plan after defaming them over 2020 election lies.

More from NBC News:

Among the items that are supposed to be turned over are Giuliani’s apartment, which is valued at $5.7 million, his collection of luxury watches, including watches gifted to him by his grandfather and the French president, a signed Joe DiMaggio jersey and a 1980 Mercedes previously owned by actress Lauren Bacall.

Some items not included in the decision are his three New York Yankees World Series rings because his son Andrew Giuliani has claimed that his father gifted the rings to him. The judge said Andrew Giuliani’s claim — and Freeman and Moss’s claim to Giuliani’s Florida condo — would be determined at a later date.

4. Rudy Giuliani To Reluctantly Pay $400,000 After Failed Last-Ditch Bankruptcy Attempt

In August 2024, Rudy Giuliani reluctantly agreed to pay a hefty fee as it relates to his would-be bankruptcy case that a judge previously rejected.

The Associated Press reported:

Rudy Giuliani has agreed to a last-minute deal to end his personal bankruptcy case and pay about $400,000 to a financial adviser hired by his creditors, avoiding a potential deep-dive into the former New York City mayor’s finances that was threatened by a federal judge.

The agreement was filed Wednesday in federal court in White Plains, New York. That came nearly three weeks after a judge there threw out Giuliani’s bankruptcy case after criticizing him for repeated failures to disclose his income sources and to comply with court orders.

5. Giuliani Disbarred In New York Amid Bankruptcy

Following a months-long review of Giuliani’s law license after it was suspended in New York and the District of Columbia, the New York Supreme Court announced on July 1 that he is no longer allowed to practice law in his hometown of New York City.

“The disciplinary charges stem from the allegations that respondent communicated demonstrably false and misleading statements to courts, lawmakers, and the public at large in his capacity as lawyer for former President Donald J. Trump and the Trump campaign in connection with Trump’s failed effort at reelection in 2020,” the New York Supreme Court wrote in its decision. “These false statements were made to improperly bolster respondent’s narrative that due to widespread voter fraud, victory in the 2020 United States presidential election was stolen from his client.”

As a result, the Court continued later in its decision, Giuliani “is disbarred from the practice of law, effective immediately, and until the further order of this Court, and his name stricken from the roll of attorneys and counselors-at-law in the State of New York.”

Read the full decision here.

6. Giuliani hits rock bottom, files for bankruptcy

In December 2023, Rudy Giuliani declared bankruptcy after a federal jury ordered him to pay two former election workers nearly $150 million for defaming them over 2020 election lies.

The filing in New York came days after the more than $148 million judgment for lies about Ruby Freeman and Wandrea “Shaye” Moss in a failed attempt to rig the 2020 election in favor of Donald Trump.

Giuliani said after the judgment that he had no regrets about the election lies he told, but the bankruptcy filing suggests otherwise.

7. Black woman who Giuliani defamed sue him again

After the verdict in favor of Ruby Freeman and Wandrea “Shaye” Moss — both of whom Giuliani repeatedly defamed and falsely accused of election fraud — the mother and daughter duo have sued the former New York City mayor again over allegations he’s doing the same thing that got him found guilty of defamation in the first place.

The new lawsuit’s primary purpose is to stop Giuliani from spreading more lies and isn’t seeking any additional monetary damages beyond having their lawyer fees paid for.

Read the full new lawsuit by clicking here.

8. Jury orders Giuliani to pay $148 million for defaming former Georgia election workers

A federal jury ruled on Dec. 15, 2023, that the man once dubbed “America’s mayor” must pay more than $148 million in damages to the former Georgia election workers whom he defamed and falsely accused of election fraud.

NBC News reported that the “eight-person jury awarded Ruby Freeman and her daughter, Wandrea ‘Shaye’ Moss, the sum after a four-day trial, during which they testified that Giuliani’s lies in support of former President Donald Trump’s bogus stolen-election claims subjected them to a torrent of racist and violent threats and turned their lives upside down.”

Giuliani is already said to be deeply in debt over the mounting legal fees he’s accrued from the need to defend himself from criminal charges he brazenly brought on himself.

The verdict came as Giuliani said he has no regrets for the election lies and tried to deflect by blaming former President Barack Obama for the nation’s racial tensions.

9. Hunter Biden sues Rudy Giuliani

On Sept. 26, CNN reported that President Joe Biden’s son, Hunter, is suing Giuliani for allegedly trying to hack a laptop and other digital devices in an apparent effort to cast shame on Trump’s political rival for the 2020 election. The lawsuit also names Robert Costello, Giuliani’s former lawyer.

10. Giuliani is deep in debt

The man once revered as “America’s Mayor” has now been revealed to be in deep debt over the mounting legal fees he’s accrued from the need to defend himself from criminal charges he brazenly brought on himself.

CNN reported on Sept. 7, 2023, that Giuliani “owes millions of dollars” and has held at least one formal fundraiser seeking handouts to help dig him out of what is presumably a continuously deeper hole. But an anonymous source “familiar with the legal defense fund” said Giuliani has only raised “peanuts” that wouldn’t even put a dent in paying off the debt owed.

Estimates place the amount owed by Giuliani at upwards of $5 million.

Trump, who has said he’s a billionaire, is apparently not offering his friend and former personal lawyer any coins, either.

11. Pay up: Judge rules Giuliani defamed Black election workers

On Aug. 30, 2023, a federal judge ruled that Giuliani is liable for defaming two Black election workers, Ruby Freeman and her daughter, “Shaye” Moss.

The two women became a target of conservatives after Trump and his allies, including Giuliani, ginned up conspiracy theories that the women mishandled ballots during the 2020 election.

According to Politico, the ruling by Judge Beryl A. Howell said that Giuliani violated her orders to preserve and produce relevant evidence to Freeman and Moss.

This ultimately led to a “default” judgment against Giuliani.

Judge Howell also ordered Giuliani to pay the two women “punitive” damages for failing to fulfill his obligations. A trial to determine the amount of damages will be set for later this year or early 2024, according to the judge. Damages could range anywhere from thousands to millions of dollars.

“Just as taking shortcuts to win an election carries risks — even potential criminal liability — bypassing the discovery process carries serious sanctions,” Judge Howell wrote.

A month earlier, a court filing revealed Giuliani made false statements about Freeman and Moss. Giuliani admitted that “such actionable factual statements” he made about Freeman and Moss “were false” but still tried to have their lawsuit against him dismissed by claiming he is protected by the First Amendment, USA Today reported. 

12. Rudy Giuliani turns himself in at Fulton County Sheriff's Office

On August 24, 2023, Giuliani surrendered to authorities and had a mugshot taken at the Fulton County Sheriff’s Office. He was indicted on charges related to attempting to overturn the 2020 election results in Georgia. He faces 13 felony counts, which include making false statements and soliciting a public officer to violate their oath. 

13. Activist holding a placard indict Rudy Giuliani. Activists…

In August 2022, Giuliani was named in Georgia’s investigation into election interference in the state during the 2020 presidential election. He was given notice to appear before a grand jury in Atlanta, the New York Times reported at the time. 

14. D.C. Bar moves to permanently ban Giuliani from practicing law

In June 2022, the District of Columbia Bar’s disciplinary branch made public a recent filing of charges against Giuliani reportedly stemming from his role in supporting lawsuits by the Trump campaign. As reported by the Associated Press, the move comes after New York and the District suspended his license to practice law.

The office of disciplinary counsel petitioned for a formal disciplinary hearing process, outlining the actions Giuliani took as counsel for the Trump campaign after the 2020 election. While the alleged improper action concerns conduct in Pennsylvania, the District of Columbia Bar maintains such action violated its standards.

15. Rudy Giuliani and son banned from Fox News

That the cable network won’t even have Giuliani — and his son, Andrew — speaks volumes, and much more clearly than his slurred words address at a Sept. 11 dinner where he unsuccessfully tried to distance himself from accused pedophile Prince Andrew. 

Politico broke the news that the Giuliani boys actually learned of their Fox News fate the night before Sept. 11, which may have explained the former New York City Mayor’s apparent intoxication in what could have been an effort to numb the pain of having the right-wing network turn on him. 

16. September 2021 – Video Shows ‘Drunk’ Rudy Giuliani Slurring Words In 9/11 Speech Weeks After Saying He’s ‘Not An Alcoholic’

A viral video of a speech Rudy Giuliani gave during a dinner commemorating the 20th anniversary of the 9/11 terror attacks suggests he may have had too much to drink or even be drunk — very drunk, in fact.

17. July 2021 – The D.C. Court of Appeals suspends Giuliani's law license in Washington

Citing court records, CNN reported that the “appeals court in DC said Giuliani would be suspended from working as an attorney in the city ‘pending outcome’ of his situation in New York.”

18. June 2021 – New York State Suspends Giuliani's Law License

The New York Supreme Court wrote in a decision to suspend Guilini’s law license that his willing participation in spreading lies and disinformation about the 2020 election “immediately threatens the public interest and warrants interim suspension from the practice of law, pending further proceedings before the Attorney Grievance Committee (sometimes AGC or Committee).”

It was a damning condemnation and suggests that Giuliani’s legal career is all but over for the 77-year-old.

19. April 2021 – Feds Execute Search Warrant

Federal investigators raided the New York apartment of president Donald Trump’s former personal lawyer Rudy Giuliani early Wednesday as part of a probe into his dealings in Ukraine.

20. Jan. 2021 – Inciting The Jan. 6 Capitol Attack

Rudy Giuliani, personal lawyer to U.S. President Donald Trump, speaks during a “Save America Rally” near the White House in Washington, D.C., U.S., on Wednesday, Jan. 6, 2021. 

21. Jan. 2021- Sued By Dominion Voting Systems

Dominion voting systems sued Giuliani for false election claims he continued to disseminate during the 2020 presidential election.

22. Dec. 2020 – Erratic Michigan House Oversight Committee Meeting

Rudy Giuliani served as legal representation during an appearance before the Michigan House Oversight Committee where he called on numerous witnesses who repeated false, damaging and racist claims regarding the 2020 presidential election. Giuliani filed several motions which eventually was rejected by the Supreme Court.

23. Nov. 2020 – RNC Presser With Hair Dye

Giuliani participated in an embarrassing news conference at the Republican National Committee regarding the frivolous lawsuits around the 2020 presidential election.

24. Oct. 2020 – Appearance in Borat Film

Giuliani was duped in the follow up to Sacha Baron Cohen’s 2006 “Borat” film, “Borat Subsequent Moviefilm.” In a disturbing scene Giuliani can be seen reaching into his pants and apparently touching his genitals while reclining on a bed in the presence of an actor portraying Borat’s daughter who poses as a journalist.