Giuliani’s bankruptcy could cost him his apartment, his jewellery and, perhaps worse, his Joe DiMaggio shirt

Disgraced former New York City mayor Rudy Giuliani filed for Chapter 11 bankruptcy in December after being ordered to pay $148m for falsely accusing two poll workers of cheating in the 2020 election.

This week, the former Donald Trump attorney sat for an hours-long deposition behind closed doors in the case, as his creditors seek to recover their money — with his treasure trove of assets revealing how they might be paid.

These assets include an array of goods, including 26 watches, diamond-encrusted Yankees World Series rings, and a replica Joe DiMaggio jersey. The money could even come from a potential lawsuit against Donald Trump.

The man once known as America’s Mayor for his leadership in the wake of the 9/11 terror attacks owes the eye-watering sum to Georgia mother and daughter duo Ruby Freeman and Shaye Moss.

On Monday – the same day he sat for a depostition – a district court judge rejected his bid to have the defamation verdict overturned. His lawyers have now vowed to appeal to the DC Circuit Court.

Beyond the two poll workers, Mr Giuliani could soon owe more money to a variety of individuals and entities as he is plagued by numerous lawsuits. He has until 18 June to file a debt repayment plan.

In January, Mr Giuliani, 79, submitted a summary of his assets, showing what he owns and how he valued his possessions.

Lawyers for the creditors’ committee argue that these assets have been “insufficiently itemized and appear to be undervalued” in court documents.

Despite questions about the accuracy of the filings, his bankruptcy creditors could eventually tap into these assets — even if they are “only a pittance compared to his debts,” Bruce Markell, a professor of bankruptcy law at Northwestern University told The Independent.

While the numbers aren’t exact, since Mr Giuliani has claimed $1.6m in state and federal exemptions, here are some of the ways his creditors could get paid.

Mr Giuliani owns a three-bedroom, three-bathroom apartment on New York’s exclusive Upper East Side, which he most recently valued at $5.6m.

The Sotheby’s listing from August, which has since been taken down, remarked on the building’s “magnificent gothic-inspired terracotta and brick façade.” Gold trimming lines the pre-war building’s wide hallways as marble spans the floors.

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Interior photos capture the penthouse’s New York City charm, with floor-to-ceiling woodpanelling, ornate wall trimmings, and dangling chandeliers. The library boasts a quaint wood-burning fireplace — with a framed Yankees player jersey hanging above. A Sotheby’s real estate agent noted the apartment also has a “semi-private elevator” and numerous large windows that offer glimpses of Madison Avenue.

In the face of all its luxury, the property has also seen its fair share of legal dealings.

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The site is also notable for being raided by the FBI in April 2021 over Mr Giuliani’s alleged dealings with Ukraine. This apartment is also apparently the scene of the alleged sexual assault, as described in a bombshell lawsuit brought by Noelle Dunphy, Mr Giuliani’s former assistant. “Giuliani insisted that Ms. Dunphy stay in a guest suite in his Upper East Side apartment,” the complaint states, before describing the alleged assault. Mr Giuliani denies the allegations.

He also pays nearly $11,000 per month in co-op fees, the filing states.

The former mayor recently expressed in a court filing that he intends to sell his Manhattan property and live solely out of his Florida home. This property is his highest reported asset, court filings show.

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Mr Giuliani also has a condo in Palm Beach Florida. The undulating pink-painted condo complex, bordered by palm trees and adjacent to a private heated pool, is just six stories high. It sits a stone’s throw from Lake Worth Lagoon, which separates Palm Beach from the rest of Florida.

The 2,000-plus-square-foot condo used to hold three-bedrooms, but Mr Giuliani said he transformed them into two “larger” ones. It also boasts sliding doors that lead to an outdoor balcony with a poolside view.

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His Florida condo is valued at $3.5m. But 2024 sales of other units in the condo complex have gone for closer to the $4m-and-above range.

The creditors’ committee filed a motion to force the sale of this property, noting it is his second most valuable reported asset. Lawyers for the committee previously argued that the Florida condo is “a significant drain on estate resources.” They noted that in January alone, the ex-mayor made two maintenance fee payments of $15,995.

Lawyers for Mr Giuliani responded in a March filing that he intends to live out of his Florida home full-time after the New York apartment is sold. If he is forced to sell his Florida home, then he will “be forced to incur expenses for alternative housing,” his lawyers argued. “Surely the Committee does not intend [Mr Giuliani] to join the ranks of the homeless?”

At a 4 April hearing, the judge didn’t rule on the motion to force him to sell his Florida place.

The judge warned Mr Giuliani’s lawyers, “Would it be a Pyrrhic victory for your client if the motion is denied? And it simply forces the committee then to ramp up other alternatives, which are more draconian than simply marketing the Florida property?”

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The former mayor divulged to the court that his 1980 Mercedes Benz SL500 convertible had been previously owned by Golden Age actress Lauren Bacall. “It makes me feel like I’m Humphrey Bogart,” Mr Giuliani said, referring to her husband and frequent co-star.

“I paid 20,000 for it,” he told the court. When asked about how he landed on the value listed in the documents, Mr Giuliani said, “I don’t know what it’s worth, but I figured I’d make it $5,000 more than I paid for it.”

Mr Giuliani valued the vehicle at $25,000. Some estimates show the current price of the classic car being worth just under $30,000.

The car has done approximately 80,000 miles, the court filing says.

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Mr Giuliani also admitted he did not have a driver’s licence; it expired, he told the court. He revealed at the February hearing that only his son, his partner, and his political adviser drive the vehicle. When asked if he drove the car, he replied, “I better not.”

Because he doesn’t drive himself, Mr Giuliani listed another payment of $1,600 per month in transportation costs, which he chalked up to Uber rides at the February hearing.

The former lawyer listed his “household goods and furnishings,” specifically mentioning his bed, couch, table and chairs, filling his nine-room Manhattan apartment as well as his Florida condo to be worth $20,000.

He also listed his TV and other electronic goods to be worth another $2,500.

On top of that he listed a storage unit in the Bronx for an unknown amount. The former mayor divulged that the unit holds awards, books and works of art that he was gifted. “I don’t think there’s anything very valuable, but just things that I’ve gotten over the years, going back to being US Attorney,” he said.

He valued his clothes as being worth $8,500. Mr Giuliani revealed at a 7 February hearing that he wears a different suit every day — and estimated spending over $700 in dry cleaning per month.

He also listed an all-encompassing “jewelry” category, valued at $30,000. This amount is noteable for a variety of reasons.

The former mayor also mentioned owning costume jewelry, including a diamond ring.

He also has quite the watch collection. He listed owning 26 watches, many of which are designer, including a Rolex and a Tiffany and Co watch.

When the former mayor was specifically asked about the Rolex, he told the court that it was a “small one” that was priced in the ballpark of $4,000 to $5,000 when he bought it. The cheapest men’s watch from Tiffany currently costs $3,100.

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“They run from about $400 to about $2,000, depending on the watch that you get,” Mr Giuliani said at the February hearing. Apparently referring to the one he was wearing, he said, “This one here is about $600.”

He also said he owns five Shinola watches, the cheapest of which are currently priced at $595.

So a lowball estimate of these eight watches would total $10,675, calling into question his $30,000 tally of all his jewelry — which also includes three coveted World Series rings.

If he is undervaluing his assets, he could be doing so for one of two reasons, Mr Markell said.

Mr Giuliani could be trying “to evade scrutiny,” explaining that “there's often a desire to undervalue stuff, just to keep it under the radar.” For instance, although the trustee “has the right to sell anything,” Mr Markell said, if the trustee notices that a watch is worth just $500, she will probably figure it isn’t worth all the time and effort involved to sell an item of such low value.

Secondly, some exemptions have monetary ceilings, sparking some to try to “undervalue property to get it under a threshold limit so that they won't take it from the debtor and try and sell it.”

A well-known Yankees fan, the former New York City mayor listed a variety of sporty items around his home. He didn’t provide a cost value for the memorabilia.

One of them is a “signed Joe DiMaggio shirt,” the filing states. Mr Giuliani once called the legendary center fielder “the greatest living baseball player” and “the personification of Yankee pride,” before renaming Manhattan’s West Side Highway after him in 1999.

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No matter how much Mr Giuliani may have idolized the Yankee player, he reportedly understood that the signed Joe DiMaggio shirt hanging above his Upper East Side fireplace was a replica.

The former mayor was gifted the number-five-emblazoned jersey in 2002 at the Joe DiMaggio Award Gala, contemporary reports reveal. The event was hosted by Brooklyn’s Xaverian High School. The school’s principal revealed to the Village Voice that it was a copy: “I gave Giuliani a certificate to say what it was, so he definitely knew it was a replica.”

Mr Giuliani, however, recently recalled the history of the jersey — and its authenticity — differently. In February, he said the DiMaggio shirt was “given to me by his doctor after he died.” He added, “And it’s signed by him. And it’s an actual home jersey of the Yankees but 1951.”

The stories behind how Mr Giuliani acquired two other pieces of Yankees merchandise — an autographed picture of Hall of Famer Reggie Jackson as well as a “signed Yankee Stadium picture” — have not been publicly documented, nor did he mention them at the February hearing.

Regardless, Mr Giuliani told the bankruptcy court that he has never had any of the sports memorabilia valued. Other signed Yankee Reggie Jackson photos have a wide range in value, from less than $100 to almost $400, recent pricetags show. Photos of Yankee Stadium, signed by all 1996 team members, meanwhile sell in the range of $1,000 to $3,000, recent sales show.

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Consistent with his love of sports, Mr Giuliani also said he owns three Yankees World Series rings.

The rings have their own documented history in Giuliani’s wardrobe — they have become a staple of his wardrobe, as he is frequently pictured wearing them.

A Village Voice article from 2007 claimed that Mr Giuliani then owned four championship diamond-encrusted rings — one for every year that the Yankees won while he was serving as New York City mayor.

A representative for the Yankees told the outlet that in 2003, Mr Giuliani paid $13,500 for his 1998, 1999, and 2000 rings. The following year, he reportedly paid $2,500 for his 1996 ring.

For all four rings, the former mayor paid a comparatively small sum of $16,000, a Yankees spokesperson told the Village Voice.

This price tag flies in the face of estimations from the New York Times, which reported in 2007 that the 1996 ring was valued at $8,000 while the 1998 ring was valued at $15,000. In more recent estimations, a 14-karat gold 1996 Yankees World Series ring sold for more than $25,000 in an auction that closed in February 2023.

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That price tag is almost equivalent to the total value of Mr Giuliani’s entire jewelry collection, calling into question his number-crunching.

These transactions notably occurred two years after Mr Giuliani’s mayoral term ended. Otherwise, it could have potentially landed Mr Giuliani into a legal pickle, since public servants cannot accept gifts over $50 from a city vendor, according to the New York City Conflicts of Interest Board.

“I paid precisely what anyone else would pay,” Mr Giuliani said, according to the New York Times.

He explained at the February hearing that former managing partner of the Yankees George Steinbrenner “had a ring made for me” every year that they won the championship while he was mayor.

“He didn’t tell me he made it for me because I turned down the first one because I didn’t think I should accept one as the mayor,” Mr Giuliani explained. “And then after I left office, he let me know that he had had them made for me, and they were given to me at a ceremony. And then I paid for them because I didn’t want anyone to say that I got something from them.”

One ring is missing from the bankruptcy court filings.

Fox Business reported in 2019 that Judith Nathan, Mr Giuliani’s ex-wife, had requested two World Series rings as part of the divorce settlement, which was finalized in 2018. It’s unclear if she ended up with one of the rings; The Independent has asked her lawyer for comment.

Mr Giuliani also mentioned that he had given the rings to his son, Andrew, at the 8 February hearing. His lawyer said curtly: “He doesn’t have possession of those.” When asked if he still has an ability to retrieve the rings, the ex-mayor replied: “Oh, I could wear one if I wanted.”

A former close associate of Mr Giuliani told The Independent that he possesses all four rings, contrary to what he told the court.

Compared to other practice areas, “the incentives to be honest and upright aren't the same in bankruptcy,” Mr Markell said. If it’s discovered that he does in fact have a fourth ring, for example, “What's the court gonna do?” he asked. Force the bankrupt Giuliani to pay a fine?

The Northwestern professor added that monthly operating reports — a bankruptcy process requirement that provides transparency into the debtor’s expenditures — “have to be accurate.” They are often signed under penalty of perjury, meaning if the debtor lies on these disclosure forms, he risks being prosecuted for perjury, non-disclosure of assets or fraudulent undervaluing, Mr Markell said.

Mr Giuliani has filed a lawsuit against President Joe Biden for defamation.

The former mayor took issue when Joe Biden called him a “Russian pawn” during a presidential debate in 2020. Mr Giuliani claimed that this description has cost him “millions and millions of dollars” from lost clients and consulting business.

Separately, Mr Giuliani claimed he is owed $2m from his former client Donald Trump in alleged unpaid wages for work he did to investigate claims of election fraud in the 2020 presidential election. Mr Giuliani has insisted that he is owed by the Republican National Committee (RNC) or the Trump campaign — not the former president himself.

The Independent previously reported that the committee is “discussing” taking legal action against Mr Trump, the Republican National Committee (RNC), and/or the Trump campaign to retrieve those funds. Mr Giuliani has insisted that he was paid by the RNC or the campaign — not his former client himself.

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“Mayor Giuliani will not be suing President Trump,” Ted Goodman, Mr Giuliani’s political adviser, told The Independent in response.

If a debtor “is shown not to be exercising their duty to maximize assets of the estate, that action can be transferred to the creditors committee,” Mr Markell said. That means, for instance, if there were a statute of limitations on that claim that expired in a month, and Mr Giuliani hadn’t done anything before then, the court likely then tell the creditors’ committee to bring this suit on behalf of the estate, therefore “they get to they get to sue Trump in Giuliani’s name.”

This is where it starts to get a little murky.

Mr Giuliani noted that he had been paying his ex-wife Judith Giuliani $5,000 in alimony payments every month, which he described at a February hearing as going “to [Judith] but for her mother.”

The filing states that he also pays $13,500 per month for “court ordered payments to mother-in-law.” Last month, Mr Giuliani’s former mother-in-law died, according to an obituary.

Both of these monthly payments have been amounting to $222,000 per year. It’s unclear how that amount will affect the creditors.

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In the January filing, Mr Giuliani reported having $50 of cash on hand as well as roughly $14,000 across his Citibank accounts.

He also wrote that he has stock in Uber shares — for an unknown amount. Additionally, he listed an unknown amount of stock or interest in three non-publicly traded businesses he owns: Giuliani Communications, Giuliani and Company, and WorldCapital Payroll Corp.

The former mayor listed that he collects more than $40,000 in income each month, describing it as “RMD” or required minimum distribution from his IRA account. It’s unclear whether that amount would be available to creditors or exempt.

There is another exempt source of cash: two legal funds. Another “unusual” aspect of this case, Mr Markell said, is that his lawyers are being paid by donors, alluding to contributions from the Giuliani Defense Fund, a PAC, and the Giuliani Freedom Fund Legal Defense, a trust fund. These funds are not accessible to creditors — however, the committee is seeking to investigate where the money came from.

The former mayor “is not spending money that’s available to creditors to help defend and prosecute these litigations,” Mr Giuliani’s lawyer Heath Berger told Bloomberg Law in February. “It’s a win-win for the estate and for the creditors because it’s money coming from a third party. That’s the best thing you can do in bankruptcy.”

Separately, when arguing against forcing Mr Giuliani to sell his Florida home, his lawyers argued in a March filing that their client uses both of his residences to operate his podcast businesses, citing that each home has a “studio.” He will “need a place to operate the Podcast from if he is to earn money therefrom,” the lawyers wrote.

Although Mr Giuliani’s lawyers noted in the January filing that he is a radio/podcast host, his monthly income was listed at $0.

Similarly, a lawyer for the committee said at the 4 April hearing, “Notably, his income does not include anything related to his podcasting business.”

Lawyers for the creditors committee have also asked the court to hire a firm that specialises in “asset tracing investigations around the world.” Former Giuliani associate Lev Parnas testifed in March that he spent “a year of traveling across the globe to find damaging information on the Bidens” at the direction of the former mayor and Mr Trump.

If the firm is retained, it’s unclear what assets, if any, would turn up or where.