The New York attorney general wants to recover $250 million from the former president and run him out of the state.
A trial in New York next month for Mr. Trump's company on criminal tax charges could cost millions of dollars in penalties and legal fees.
Some of his advisers fear that civil suits from people who want to hold the former president responsible for injuries and trauma suffered during the January assault on the Capitol could be very costly to him.
There are many investigations and lawsuits surrounding Mr. Trump.
There is no evidence that he is facing a crisis right now. Eric Trump said in an interview that the Trump Organization had recently paid off some debts and had a windfall from the sale of the Trump International Hotel.
Even as he continues to signal that he plans another run for the White House, the potential costs that the former president faces show that his challenges go beyond the courtroom and into the upkeep of his wealth.
The merger of his social media company with another company is hanging by a thread because of regulatory and law enforcement scrutiny.
Even though Mr. Trump is a formidable political fund-raiser, his situation is complex. He could face restrictions on his personal use of money he has kept in his main political action committee if he becomes a presidential candidate.
The kind of legal cases that the Trump Organization faces can hurt any corporation, according to John A. E. Pottow, a professor of commercial law.
There is a company that has serious litigation risks. They have a lot of liability on the way.
The empire is being scrutinized. New York State's attorney general has been investigating Donald J. Trump's business practices for several years. This is what to know.
The inquiry's beginnings are outlined. The investigation began after Michael D. Cohen testified to Congress.
There are possibilities of penalties. Ms. James wants to prevent Mr. Trump and his children from ever opening a business in the state again. The findings have been referred to federal prosecutors.
The experts said that Mr. Trump would be able to weather the storms. The Trump Organization generated hundreds of millions of dollars from the sale of its Washington hotel, as well as from other recent deals, and it has either refinanced or paid off a lot of its loans.
A person with knowledge of the company's performance says that Mr. Trump's hotels have rebounded from deep losses incurred in the early days of the coronaviruses epidemic.
His golf clubs, many of which saw a surge in business during the Pandemic, have begun to attract new tournaments in recent months.
Most of the family's real-estate assets are free and clear, and they have low debt, according to Eric Trump. Mr. Trump and his family, including Eric Trump, were accused of overstating the value of the company's assets.
The various investigations were described as "weaponized government" by the former president's spokesman.
Mr. Trump has faced legal and financial challenges before. In the early 1990s, he faced financial ruin after filing and defending dozens of lawsuits. His current problems are not as bad as those challenges.
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Some of Mr. Trump's recent gains could be in jeopardy due to his legal troubles.
The former president and three of his children are being sued by Ms. James. She is trying to stop Mr. Trump from buying real estate in New York. The office of Ms. James is trying to shut down some of his New York operations.
The case against Mr. Trump and his family business had no immediate impact on the company.
The case could take years to play out in the courts, and a judge would have to grant the punishments Ms. James is seeking. The case could be settled before it goes to trial.
The criminal tax fraud trial of the Trump Organization will start in New York next month. The company was accused of conspiring with its CFO, Allen Weisselberg, to avoid taxes.
Mr. Weisselberg pleaded guilty to taking part in a scheme that included receiving a rent-free apartment, leased Mercedes-Benzes and private school tuition for his children. He agreed to testify at the company's trial in order to help prosecutors.
A judge could impose a small penalty if the company is found guilty. It will incur a large amount of legal fees and could face trouble with the local authorities, who might shy from doing business with a company convicted of a felony. The Trump Organization entities that are under indictment are not thought to have any loans or liquor licenses.
Mr. Trump is facing a number of investigations and legal costs related to his efforts to hold onto office after he lost the 2020 election, as well as his taking and then refusing to return presidential records and more than 300 individual documents marked classified when he left office He paid a lawyer $3 million to defend himself in those cases.
There is a dispute between the I.R.S. and Mr. Trump that is not clear.
There are at least seven civil lawsuits that are trying to hold the former president accountable for the chaos and violence that erupted at the Capitol in January of 2021. The people close to Mr. Trump think there will be more suits.
The suits against Mr. Trump were given the go-ahead by a federal judge in Washington because he was immune from civil litigation. The judge said that the people could try to prove that Mr. Trump was involved in a conspiracy with the mob. The former president is appealing the judge's decision.
Alan Z. Rozenshtein, a former Justice Department official who is a professor at the University of Minnesota Law School, said that if the suits against Mr. Trump were successful, calculating the amount that he might have to pay in damages would depend on the individual cases. Members of Congress and Capitol Police officers are included.
Phillip A. Braun said that a fine like that would not bring the company down. Liquidating some of the family's properties would probably be the best way to go about it.
Money was not a concern when Mr. Trump was in the White House. He was poised to cash in on his appeal in conservative media circles, including through his social media venture, the merger of the parent company of Truth Social with a special purpose acquisition company called Digital World Acquisition Corp.
Both the S.E.C. and federal prosecutors are investigating the deal. The original deadline for completing the deal has passed and Digital World could be in danger of going out of business.
Most of the company's shareholders are retail investors, so the company's promoter is hoping that they will give them more time to complete the deal. The deal between Digital World and Trump Media & Technology Group is not expected to be approved by the S.E.C.
Regulators and federal prosecutors in Manhattan are looking into potentially improper communications between representatives of Digital World and Trump Media. Unusual trading in Digital World's stock is being looked at.
Digital World raised $300 million in cash in its public debut. Dozens of hedge funds agreed to provide an additional $1 billion in financing after the two companies announced their merger. Mr. Trump got on the phone with some of the big investors who were willing to commit at least $50 million to help complete the merger.
The inability to complete the merger in time resulted in the end of the financing deal. Digital World and Trump Media may not be able to convince investors to sign onto a new agreement given the legal uncertainty surrounding the merger. Digital World's share price has plummeted.
Alan Feuer reported.