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Trump’s Crumbling Empire Faces Long Odds For A Comeback

On the day Donald Trump was getting impeached in Washington, the lobby of his New York tower at 40 Wall St. was almost silent. Few footsteps smudged the shiny marble. Trump’s Crumbling Empire Faces Long Odds for One More Comeback

But up the dark and golden elevators, trouble was stirring in one of the billionaire’s most valuable properties. Inside one law office, two partners had clashed over whether to keep paying rent to a landlord who encouraged the Capitol’s deadly riot. On the 24th floor, a nonprofit that fights tuberculosis was exploring options for leaving. On the seventh, the Girl Scouts were figuring out how to break their lease.


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And in the basement, vintage bank-vault doors that weigh more than 10 tons stood wide open. There, in a club room that Trump renovated, the news was playing on a jumbo television to an audience of empty armchairs just as Congress voted against him.

So it goes in Trump’s empire as his presidency slouches toward the end.

The Trump Organization, run by sons Eric and Don Jr., was struggling with the devastating consequences of the Covid-19 pandemic even before their father incited a raid on Congress. Efforts to sell his Washington hotel were shelved, his office buildings were losing value amid a glut of space in Manhattan, and his golf courses were facing the reality that younger generations aren’t so interested.

Trump entered office worth $3 billion. Despite soaring stock prices and his own tax cuts, he will leave about $500 million poorer, according to the Bloomberg Billionaires Index.

His buildings are saddled with more than $1 billion in debt, most of it coming due in the next three years and more than a third of it personally guaranteed. Refinancing would mean finding lenders and corporations willing to work with history’s only twice-impeached ex-president.

“Nothing like this has ever happened to him,” said Barbara Res, who was an executive in Trump’s company for years. “Will he come back? My gut tells me yes, because he always comes back. But he won’t come back the same.”

Deserted Avenue

Trump already has survived corporate bankruptcies, rough times in Atlantic City, a school that ended with probes and dead-end brand journeys for Trump Steaks, Trump Vodka and even an airline. The man who made “America First” his catchphrase could now hunt overseas for partnerships and licensing deals.

Even so, Deutsche Bank AG, his longtime financier, won’t touch him anymore. Signature Bank, where his daughter Ivanka once served on the board, is closing his accounts. Cushman & Wakefield Plc, a broker for 40 Wall St., is cutting ties, and PGA of America is steering clear.

The biggest hits to Trump’s fortune are in New York, the heart of his empire, where the Queens-born developer turned into a reality star and then descended his own escalator to enter politics.

Outside Trump Tower, East 56th Street remains blocked, a parking lot for about a dozen black SUVs with government plates. The building is closed to visitors due to the pandemic, shutting Trump’s grill, bar, cafe and ice cream parlor.

Not that there are tourists around for winter sundaes. Fifth Avenue is almost deserted. Vacant storefronts are multiplying, and some remaining boutiques are now appointment-only. Rents have slid 32% from a 2018 peak, according to the Real Estate Board of New York.

Trump’s cavernous East 57th Street space is currently subleased to the iconic Tiffany’s jewelry store, but a new tenant will soon be needed.

High above, 1,596 square feet of Trumpian extravagance keeps getting cheaper.

Apartment 55B, with blue lapis floors and medallion ceilings, is listed for $2.995 million, about $2.5 million less than four years ago. It’s hardly an outlier. Prices at the skyscraper have slipped by a third since Trump took office, StreetEasy data show.

And even before the Capitol attack, his company was offering concessions to some tenants at 40 Wall St., lender records show. The $137 million debt at the property was added to lender watch lists in November after net income dipped below what underwriters expected when the debt was issued in 2015.

City’s Rejection

“I don’t believe his name is going to bring a premium currently,” said Warren A. Estis, founding partner at real estate law firm Rosenberg & Estis and owner of an 86th-floor penthouse at Trump World Tower near the United Nations. Still, Estis said he’s heard no rumblings from his condo board about stripping Trump’s name from the building.

“What’s in a name? A rose by any other name is still a rose,” says Estis. “It appears Donald is very resilient and I expect he’s going to bounce back from this.”

New York City itself wants nothing to do with Trump. Officials plan to end more than $17 million in contracts with the president’s family business, including a carousel and two ice skating rinks in Central Park and a Bronx golf course.

“The City of New York has no legal right to end our contracts and if they elect to proceed, they will owe the Trump Organization over $30 million,” the company said in a statement. “This is nothing more than political discrimination, an attempt to infringe on the First Amendment, and we plan to fight vigorously.”

While police officers were keeping the public out of Trump Tower, including its Trump Store, there was also bad news for fans going online to nab Trump pint glasses for $55 or a Trump candle set for $80. Shopify is refusing to service the website, which has left customers with a warning that their connection isn’t private and “attackers might be trying to steal your information.”

Not long ago, the big question hovering over Trump’s return to the business world was whether the former reality television host would make a foray into conservative media, where product endorsements and licensing deals are legion. Now the talk in finance circles centers on whether he can defend his existing empire. He’ll have to convince lenders he’s worth the risks, and prove to developers his name retains enough cache.

“The presidency and Donald’s racist, sexist and xenophobic language has tarnished the brand to such an extent that it is valueless,” said Michael Cohen, his lawyer-turned-critic.

Streaming Trump

Eric Trump brushed off such assertions in an interview with the Associated Press this week, blaming “cancel culture” for recent hits to the family empire that he said posed no threat to the company’s finances. His father, he noted, still has armies of fans: “You have a man who would get followed to the ends of the Earth by a hundred million Americans.”

One executive in conservative media who’s still bullish on Trump’s prospects for creating a subscription-based video service conceded that recent events may limit possible platforms, advertisers and partners.

Still, the executive said that even controversial porn purveyors can find homes online. He estimated Trump could get 5 million to 15 million supporters to pay $10 a month for content, predicting gold hawkers and close friends wouldn’t balk at advertising.

The Trump Organization could also look overseas.

During his presidency, Trump pledged that his businesses wouldn’t sign new deals in foreign countries, but it continued to collect income from licensing arrangements in Turkey, the Philippines and India. His administration developed close ties in the United Arab Emirates, where he’s previously done business, and Saudi Arabia, where his company considered projects before his ascent to the presidency.

Betting On Rebound

Hussain Sajwani, chairman of Dubai’s DAMAC Properties, said he’d welcome the chance to expand his firm’s relationship with Trump.

“We have a great relationship with the Trump Organization, and, be assured, we have absolutely no intention to cancel our agreement,” he said in a statement.

The author of “The Art of the Deal” and “The Art of the Comeback” could try his hand at returning to publishing. Trump’s predecessors in the White House, President Barack Obama and First Lady Michelle Obama, got a record-breaking $65 million advance for their memoirs.

Trump may have created problems for himself here, too. Publisher Simon & Schuster canceled a planned book by Trump ally Josh Hawley, citing the Missouri senator’s “role in what became a dangerous threat to our democracy and freedom.”

At least for now, a return to politics isn’t out of the question. Betting website PredictIt pegs the odds that Trump will file this year to run again for president at about 30%. Recently, like so much else, that number has taken a tumble.

Updated: 1-19-2021

London Neighborhood That Trump Called Lousy Is Now One of City’s Hottest

Nine Elms, a formerly industrial area of the U.K. capital, is luring the likes of Apple and luxury hotel operators.

President Trump once dismissed the London neighborhood of Nine Elms as “lousy” and “horrible.”

Mr. Trump made his remarks in 2018, after the American Embassy left its historic base in upscale Mayfair for a newly constructed building 3 miles south.

Today, Nine Elms is emerging as one of London’s hottest real-estate markets. The 561-acre tract of formerly industrial land beside the Thames is luring big tech names like Apple Inc., an American book publisher and luxury hotel operators. The district will soon be home to what a developer says will be the world’s first “sky pool,” which will sit suspended between two towers.

Nine Elms’ redevelopment started a decade ago and now features more than 40 individual projects with a combined cost of £15 billion, equivalent to $20.5 billion. When the projects are completed around 2030, more than 25,000 people are expected to work in the district and as many as 40,000 people will call it home.

Home prices have been rising, despite the pandemic, which slowed overall sales activity. The average price of a Nine Elms apartment crossed the $1 million mark for the first time last year. That price was $1,086,180 at the end of 2020, up 13% from the end of 2019, according to property portal Zoopla.

Apple plans this year to move to Nine Elms, taking 500,000 square feet of office space within Battersea Power Station, a decommissioned coal-fired power plant at the west side of the neighborhood that is being renovated. About 1,400 employees from around London will be based at the landmark building, owned by a consortium of Malaysian investors, making it one of the tech giant’s largest sites outside North America.

A new metro station, linking the neighborhood to the London Underground network, is also poised to open this year. Hyatt Hotels Corp. said it plans to open a 203-room Park Hyatt hotel in Nine Elms as early as next year.

“It’s an area we believe will see huge demand for both leisure and business travel,” said Felicity Black-Roberts, Hyatt’s vice president of development, Europe.

New residential projects include Embassy Gardens, which features the sky pool. The joint development by Irish house builder Ballymore and EcoWorld London, part of Malaysian developer Eco World International, will include 1,500 apartments upon completion later this year. It will also be home to offices for New York-based publisher Penguin Random House.

The initial focus at Nine Elms has been apartment buildings. Mayrow Short, head of real-estate agent Savills’ local office, said the best apartments—those on upper floors with views of the Thames—change hands at up to £2,500 a square foot, a similar rate as in London’s prime central zone, which includes Mayfair.

Battersea Power Station will offer a shopping mall with high end brands including Hugo Boss and MAC Cosmetics, bars and restaurants, an art house movie theater and event spaces.

There are also plans for the refurbishment of New Covent Garden Market, the U.K.’s largest wholesale fruit, vegetable and flower market, with more homes, offices, retail and leisure facilities.

Not every Londoner disagrees entirely with Mr. Trump’s assessment. Tom Floyd, sales director at real-estate agent Winkworth, said a majority of homes at Nine Elms are owned by overseas investors who rent them out. Its transient population means, he added, the area lacks a sense of community and some buildings are apparently largely empty.

“If you drive past there are no lights on in the evening,” Mr. Floyd said.

But he is hopeful. “I think that when Battersea Power Station opens it will really be the epicenter of Nine Elms, because it will become a destination,” Mr. Floyd said. “I think it will be great. It is just not a finished product.”

Updated: 1-20-2021

Trump Reveals Extent of Pandemic Damage To His Business Empire

Trump’s Crumbling Empire Faces Long Odds For One More Comeback

Donald Trump’s empire has been hit hard by coronavirus closures, with revenue from his Washington and Las Vegas hotels down by more than half.

In his last financial disclosure form as president, Trump detailed the damage the pandemic has wrought, at a time when many tourism businesses are suffering from a lack of travelers. As president, the real-estate magnate resisted policies to slow the pandemic through mask-wearing, and insisted it remained safe for people to travel domestically.

Revenue from the Trump hotel in Washington, which he had been trying to sell, fell to $15.1 million from $40.5 million a year earlier, according to the disclosure posted Wednesday. In Vegas, hotel-related sales were down to $9.2 million from $23.3 million. Another important property of Trump’s, the Doral Golf Resort in Miami, also saw revenues drop to $44 million from $77 million a year earlier.

His golf courses in the U.K. and Ireland saw revenue drop by roughly two-thirds, part of a 27% overall decline in golfing revenue from the prior year.

Trump’s total income fell to between $273 million and $308 million, according to the form, which covers 2020 and the first 20 days of 2021. In his first financial disclosure in 2017, Trump reported making more than $528.9 million over 15 1/2 months, including his first three months as president.

One bright spot in Trump’s empire is his Mar-a-Lago club in Florida, where the ex-president returned today after his final day in the White House. Revenue for the club hit $24.2 million, up from $21.4 million a year earlier, according to the financial disclosure. It’s one of Trump’s few properties that seems unaffected by the pandemic.

He also reported an uptick in online retail sales year-over-year, up to $1.96 million from $930,869 in 2019. However, in-store sales at Trump Tower in New York City fell because of forced closures — down to $166,064 from $849,313.

In total, Trump valued the assets from his businesses at between $1.3 billion and $1.7 billion. The disclosures are not exact — federal officials give the value of their assets and income in broad ranges, and the top value is “over $50 million.” Trump had 22 assets he listed in that range, including his Mar-a-Lago resort and the Trump International Hotel in Washington.

The form also details more than $40,000 in gifts Trump accepted in his last year in office, including freebies from executives at Boeing Co., Apple Inc. and Ford Motor Co.

Trump is worth $2.5 billion, down about $500 million from when he took office, according to the Bloomberg Billionaires Index. His buildings are saddled with more than $1 billion in debt, most of it coming due in the next three years and more than a third of it personally guaranteed.

Updated: 1-20-2021

China Sanctions 28 Trump Aides

The White House called last-minute Chinese sanctions on former Trump administration officials “unproductive,” saying they were an effort to sow partisan rancor as Joe Biden takes office.

“Imposing these sanctions on Inauguration Day is seemingly an attempt to play to partisan divides,” a National Security Council spokeswoman Emily Horne said in a statement late Wednesday. “Americans of both parties should criticize this unproductive and cynical move. President Biden looks forward to working with leaders in both parties to position America to out-compete China.”

Beijing sanctioned former Secretary of State Michael Pompeo and other Trump officials just as Biden was being inaugurated, hitting back at the outgoing team while leaving open the possibility of warmer ties with their successors.

Also on the list of 28 people being sanctioned were former President Donald Trump’s National Security Adviser Robert O’Brien and his deputy Matt Pottinger, trade adviser Peter Navarro, and U.S. Ambassador to the United Nations Kelly Craft, according to a statement issued Wednesday by China’s Foreign Ministry. They and their families will be restricted from entering China, Hong Kong or Macau, or doing business with China.

The officials listed were instrumental in shaping the Trump administration’s more confrontational stance toward China, which included a raft of sanctions and a declaration, on its final day, that the government had committed genocide in its Xinjiang region. Also on the list were former Trump adviser Steve Bannon and former National Security Adviser John Bolton.

This brings the number of U.S. officials sanctioned by China to at least 44, according to data compiled by Bloomberg, which is broadly on par with the tally of Chinese people sanctioned by Washington.

The officials “planned, promoted and executed a series of crazy moves which have gravely interfered in China’s internal affairs, undermined China’s interests, offended the Chinese people, and seriously disrupted China-U.S. relations,” the Foreign Ministry said in a statement. The statement didn’t list all the people affected by the restrictions.

The move came after the Chinese Foreign Ministry had this week urged “mutual respect” with the incoming Biden administration after years of worsening tensions under Trump.

Still, Greg Gilligan, chairman of the American Chamber of Commerce in China, said the new sanctions wouldn’t prevent Biden from trying to ease tensions with Beijing.

“The timing is unfortunate, given it’s the first day of the new administration,” he told Bloomberg TV. “However, it was also very clearly directed at the outgoing administration. So China’s saying, ‘We’re going to stand our ground.’ I don’t think it erases the possibility for a reset. I do think there’s been plenty of signals that suggest a reset is possible.”

‘Significant Challenge’

Although Biden and his team are unlikely to match the harsh rhetoric leveled by Pompeo and other Trump administration officials, they have indicated they aren’t ready to ease tensions as much as China’s leaders would want.

Retired General Lloyd Austin, Biden’s nominee for defense secretary, said in a written submission for his confirmation hearing on Tuesday that the new administration “will view China as our most serious global competitor and, from a defense perspective, the pacing threat in most areas.”

The same day, Biden’s pick for secretary of state, Antony Blinken, said at his hearing that China is “the most significant challenge of any nation state to the United States in terms of our interests, the interests of the American people.”

But he said he saw some room for cooperation “when it is in our mutual interest.” Biden’s transition team has said it hopes to forge some agreement with China on climate change and nuclear arms control.

Those targeted by China’s sanctions on Wednesday are likely to wear the restrictions as a badge of honor. Pompeo, who railed against China in a string of tweets in recent days, may boast of his tough stance in a future political campaign.

“I’ve been sanctioned by the Communist Chinese government for ‘nasty behavior,”’ Bolton tweeted Wednesday. “Great news for an inauguration day! I accept this prestigious recognition of my unrelenting efforts to defend American freedom.”

It’s not the first time China has sanctioned top U.S. officials. In July, the country announced sanctions on Republican senators Marco Rubio, Ted Cruz and other officials over what the foreign ministry said was interference in China’s internal affairs.

Updated: 1-22-2021

Trump’s Loan Extension On A Manhattan Building Shows His Debt Options

A recently refinanced mortgage for a building in Manhattan may show how Donald Trump is able to deal with his upcoming debt maturities, albeit at a higher cost.

Investors Bank agreed to extend the mortgage on Trump Park Avenue, a condo building at the corner of 59th Street, by a year to 2021, according to his latest financial disclosure, released hours after he left office.

The interest rate increased 25 basis points to 3.5%. It’s at least the second time the due date has been pushed out since the $23 million loan was originated in 2010, records show. It’s now estimated to be less than $10 million.

Michael Cohen, Trump’s former attorney and fixer, owns a unit there, and other owners have included former baseball star Alex Rodriguez. When Ivanka Trump and Jared Kushner lived in the building, Rupert Murdoch and his then-wife Wendi Deng reportedly were among their neighbors, Deng said in 2010.

It has since lost some of its cachet. Seven of eight units listed for sale last year on StreetEasy failed to sell. Most were then listed for rent. A one-bedroom condo on the ninth floor that was listed for $2.1 million in 2019 could be rented for $3,600 a month as of last week. The Trump Organization developed the building and still owns more than a dozen of the units, which form collateral for the mortgage.

Brian Doran, general counsel at Investors Bank’s parent company, declined to comment.

Doral Resort

The Trump Organization has almost $600 million of estimated debt coming due within the next four years. These include loans tied to Trump Tower in New York and the Doral Golf Resort outside Miami, where revenues dropped to $44 million last year from $77 million a year earlier.

With longtime lender Deutsche Bank AG refusing to work with the former president, and corporations distancing themselves from the family business, that has raised questions over how easily the debt can be refinanced.

Trump’s business would be far from alone in changing loan terms during the pandemic. There’s been a significant increase over the past year in commercial mortgage modifications, particularly in New York City, as Covid-19 wrecked property valuations, halted foreclosures and evictions, and allowed millions of people to temporarily stop paying rent.

More than 10% of all commercial mortgages that have been bundled into securities have requested some kind of relief from creditors during the pandemic, said Manus Clancy, a senior managing director at data provider Trepp LLC. Most of those debtors were hotels and retail businesses, he said. Residential property owners have yet to face similar levels of distress.

Representatives of the Trump Organization didn’t respond to a request for comment.

The mortgage on his Park Avenue building was one of a few loans that came due during Trump’s first term. Three mortgages were paid off in 2017, while the due date on a loan for his Seven Springs estate in Mount Kisco, New York, was extended to 2029 from 2019. The rate on that mortgage increased to 4.5% from 4%.

Updated: 2-24-2021

Kushner’s Times Square Center Moves Toward Foreclosure

A Times Square retail property owned by Kushner Cos., the family company of former presidential adviser Jared Kushner, is a step closer to foreclosure, according to loan documents.

“Legal counsel has been engaged and foreclosure actions have been filed,” according to a report compiled by Wells Fargo & Co., the trustee on the debt.

Representatives for Kushner Cos. didn’t immediately respond to a request for comment.

The building at 229 West 43rd Street, which used to house the New York Times, is only about half occupied. It was reappraised at $92.5 million in 2020 and counted Bowlmor and, until December, Guitar Center as tenants. The building was appraised at $470 million in 2016.

Deutsche Bank AG originated a $285 million loan in 2016 to refinance six floors of retail space in the former New York Times building. The property also had $85 million in mezzanine debt from SL Green Realty Corp. and Paramount Group Inc.

The property was running into trouble even before the pandemic turned Times Square into a ghost town. Rent income was falling short of interest payments on the debt back in November 2019.

A month later, the loan was transferred to special servicing “due to imminent monetary default,” according to Wells Fargo.

Updated: 4-22-2021

Kushner Family Business Unloads Thousands of Maryland Apartments

Kushner Cos. sold two apartment complexes in the Baltimore area for a total of $240 million, part of an ongoing push by the company to unload about half of its assets in Maryland, a person familiar with the sale said.

The company formerly run by Donald Trump’s son-in-law Jared Kushner also has buyers lined up for six additional complexes in the Baltimore area and earlier this year sold another pair of apartment buildings there for a combined $69.3 million, said the person, who asked not to be identified because the information isn’t public.

Laurent Morali, the company’s president, said the Maryland properties — which were purchased a decade ago — had reached the end of their investment horizon.

“We are following through with our original business plan to create an exit for our partners after 10 years of ownership,” Morali said Wednesday in an emailed statement, declining to comment further.

Sales of the other half-dozen Baltimore-area buildings are expected to close within the next few months, said the person, who declined to identify the buyers or say how much they were paying.

Morali told the Real Deal in December that he expected all 10 Maryland complexes — which comprise thousands of apartment units — would sell for a total of $800 million. Kushner Cos. has been working with three brokers on the sales: Berkadia, CBRE and Newmark.

Florida Expansion

The company’s Westminster Management oversees more than 24,000 apartment units in New York, New Jersey, Maryland, Virginia and Tennessee, according to its website. Kushner Cos. is currently expanding into Florida, with plans to develop apartment buildings in Miami and Fort Lauderdale. The firm first established a presence there in 2019, before the pandemic sent hoards of people to South Florida to ride out the pandemic in good weather.

While expensive markets such as San Francisco and New York are experiencing vacancies, rent is on the rise in much of the U.S. as workers untethered from offices relocate to cheaper areas. The median rent on a one-bedroom apartment in Baltimore County soared 22% to $1,445 in the 12 months through February, according to a recent report from listing site Zumper.

The Maryland properties being sold by Kushner are part of a 2019 lawsuit brought by the state’s attorney general, who claimed Westminster Management engaged in numerous “illegal and harmful” practices. The firm lied about the quality of rental units and the level of maintenance it would provide, and routinely failed to address hazardous conditions such as rodent infestations, water leaks and mold growth, Attorney General Brian Frosh said in a statement at the time.

The case is still active, awaiting a decision from the administrative law judge, a spokeswoman for Frosh’s office said in an email. The sale of the properties won’t affect the case, she said.

Updated: 6-25-2021

Trump Organization Expects To Be Charged In New York Tax Case

New York state prosecutors are likely to charge the Trump Organization in coming days, but not former President Donald Trump himself, a lawyer for the company said.

The company expects to be accused of tax crimes relating to its payment of perks and benefits to favored employees, Ronald Fischetti said on Friday, a day after he and other defense lawyers held a Zoom meeting with prosecutors from Manhattan District Attorney Cyrus Vance Jr.’s office.

“They’re looking at charging the corporation or corporations tied to tax charges,” Fischetti said. “Donald Trump is not being indicted.”

The prosecutors are also targeting Allen Weisselberg, the company’s chief financial officer, Fischetti said. Weisselberg’s lawyer, Mary Mulligan, didn’t immediately return a call and email.

The charges would mark an extraordinary escalation of a years-long investigation into Trump and his family business. Never before have prosecutors struck so closely to a former president, and Trump is certain to cast the charges as a political vendetta by a Democratic district attorney.

It’s unclear if prosecutors will continue to explore charges against Trump.

Perks, Benefits

Fischetti said the charges will relate to an array of perks and benefits that prosecutors say were not recorded accurately in the company’s books and tax returns.

The charges aren’t expected to end Vance’s investigation into the Trump Organization or Weisselberg, according to a person familiar with the matter who declined to comment publicly on confidential negotiations.

A spokesman for Vance’s office declined to comment.

Prosecutors in the past year have combed through Trump’s taxes and business records. They have also scrutinized an array of perks that Weisselberg and the Trump Organization bestowed on favored employees, including Weisselberg’s son, to determine whether appropriate taxes were paid.

The potential charges were first reported by the New York Times.

Updated: 7-2-2021

Trump’s Former Executives Wonder If It’s ‘Beginning of the End’

When the former Trump Organization executive Barbara Res saw that the company’s longtime finance boss had turned himself in to face state tax charges, her mind turned to Donald Trump.

“This is it,” Res said. “I think that it’s going to destroy the Trump empire.”

Louise Sunshine, who was once an executive vice president, had a similar thought. “It’s the beginning of the end of the brand,” she said. But her former boss? “Donald will always survive — even if everybody else around him drops dead.”

After Abe Wallach saw the news on TV from his Southampton home, the main thing he felt was sorry for Allen Weisselberg. “He stayed too close to the fire and he got burned,” said the company’s former vice president for acquisitions. “And that’s true of lots of people.”

The Trump Organization and its chief financial officer pleaded not guilty Thursday to charges of tax fraud, scheme to defraud, conspiracy and falsifying business records, the first criminal case to emerge from the years-long investigation of Trump and his business dealings. The indictment alleges that Weisselberg, 73, received $1.76 million in unreported benefits over 15 years on which he should have paid taxes.

To outsiders, it’s the biggest legal challenge yet among many that the ex-president is facing. The way the billionaire’s current allies put it, he’s the victim of a witch hunt that’s relying on obscure rules taxing perks. And for the former executives who’ve watched the real estate heir up close, through the twists and turns of his momentous rise, operatic falls and many improbable comebacks, the charges mean something may have finally changed.

“He’s definitely in a situation he’s never been in before — because his company has been indicted,” said Res, who oversaw Trump’s construction in the 1980s and wrote a book about it called “Tower of Lies.” “I don’t think he can come back better than ever.”

In a statement, the Trump Organization called the case “a criminal prosecution involving employee benefits that neither the IRS nor any other district attorney would ever think of bringing,” and said it “is not justice; this is politics.” Weisselberg will fight the charges in court, according to his lawyers.

When financiers see the charges, their thoughts may turn to the company’s ability to refinance more than $590 million of debt coming due within the next four years — more than half of which Trump personally guaranteed. The direct consequences of any criminal conviction “could be a massive fine,” probation, or “some type of court supervision,” said former prosecutor Miriam Baer.

On Thursday, Trump’s former executives were spending more time thinking about Weisselberg, a loyal aide to the billionaire for decades. He was “the sweetest” colleague, according to Sunshine.

“His father put him there to check up on Donald,” she said. “I’ll tell you, Fred Trump would come out of his grave for this.”

Res remembers the finance chief worshiping their boss. “He called Donald ‘Mr. Trump,’ which none of us did,” she said. “On a personal level, it’s too long ago that I stopped feeling sorry for Allen.”

Wallach recalls him as more scared than adoring. “He was petrified of Donald,” he said. “Allen’s an accountant, a competent guy.”

Weisselberg was also charged with grand larceny, which carries a maximum sentence of 15 years. The executive will have months to decide whether to fight the charges or plead guilty and strike a deal with prosecutors. Jeremy Temkin, a former prosecutor, said that the question isn’t whether this is the strongest case they can make against the Trump Organization, “but whether this is the strongest case they can make against Weisselberg,” because it’s “all about putting pressure on.”

A few years ago, Wallach might have had the courage to predict Trump would escape danger. “I thought he had the luck of the gods” and “always landed on his feet.” Now, he said, “I don’t know anymore.”

Overcoming Odds

So far this year, Trump stoked a protest at the U.S. Capitol that turned deadly, survived a second impeachment trial and got cut off by his biggest banks, all while refusing to acknowledge November’s electoral defeat. But chaos isn’t out of place in the shambolic business career of a real estate heir who weaves in and out of peril.

As Trump’s empire crumbled in the early 1990s, his exuberance made his own accountants think he was hallucinating from the pressure, he wrote in “Trump: Never Give Up.” “When I hear the word ‘No’ it becomes a challenge to me,” he said. The book’s chapters include “Failure Is Not Permanent” and “Don’t Let Fear Stop You — Even in Front of Millions of People.”

In another book, “How to Get Rich,” Trump listed Weisselberg second among the “home-run, grand-slam people” that surround him. “He runs things beautifully. His team is tight and fast, and so are our meetings.”

In the last few weeks, Trump has restarted his campaign-style rallies, visited the southern border to tout his immigration policies, and has been holding out the prospect he could run again for the White House. His allies don’t seem worried by the charges.

“The more they keep persecuting the president and the people around the president, the stronger he gets,” said John McLaughlin, a Trump campaign pollster. “The base gets galvanized by this.”

Sunshine, who says she voted for Trump in 2016 but not in 2020, has two thoughts when she considers the fate of his empire.

“He always thought he had this down, he had the right lawyers, he had the right this, he had the right strongman, but I think this time he doesn’t have the right thing — this time it’s bigger than him,” she said. “The problem is that his loyal cadre of people who keep helping him recover is getting smaller and smaller.”

On the other hand, when it comes to his own career, “he survives everything,” Sunshine said. “He’s a super-human. I don’t find it impressive, I find it a reality.”

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