In two courthouses, two blocks apart, two New York judges could well ruin Donald J. Trump’s week.
On Thursday, one of the judges, Juan M. Merchan, may schedule the first criminal trial of a former American president for as early as next month — raising the specter that Mr. Trump might end up behind bars.
The following day, according to two people with knowledge of the matter, the second judge is expected to deliver a ruling that threatens not Mr. Trump’s freedom, but his family business. The judge, Arthur F. Engoron, oversaw the former president’s civil fraud trial and is weighing the New York attorney general’s request to penalize Mr. Trump hundreds of millions of dollars and sever him from the company he ran for decades.
The dual threats represent a turning point in Mr. Trump’s legal odyssey, a week that could reshape his personal and presidential fortunes as he marches toward the Republican nomination. Justice Engoron’s ruling could drain Mr. Trump’s cash coffers, and if the former president ultimately leaves Justice Merchan’s courtroom as a felon, it would send the country’s already bitter politics into uncharted realms.
Mr. Trump has used the New York cases to falsely portray himself as a victim of a Democratic cabal bent on persecuting him and aiding his presumptive general election opponent, President Biden. And he has repeatedly attacked the two Democrats who brought the cases — the Manhattan district attorney, Alvin L. Bragg, who filed the criminal charges, and the New York attorney general, Letitia James, who led the fraud lawsuit.
But Mr. Trump’s New York week underscores the limitations of one of his battle-tested legal strategies: delay. Ms. James had to fight through two years of litigation before filing her lawsuit, and it took the district attorney’s office five years to bring an indictment. But both cases have wound their way through the legal system to become immediate threats to the former president, and at an inopportune time.
His legal imbroglio, of course, does not stop in New York. Mr. Trump faces 91 felony counts across four criminal cases, in Washington, Florida and Georgia as well as Manhattan. On the civil front, he must contend with Justice Engoron’s fraud ruling and with the $83.3 million he owes from a recent defamation case.
Thursday will be particularly hectic. On the same day, and at the same hour that Justice Merchan is expected to rule, the Georgia prosecutor who accused Mr. Trump of conspiring to overturn the 2020 election will face a hearing about her romantic relationship with a lawyer she hired to work on that case. As of Monday morning, Mr. Trump was still in discussions about whether he would attend one of the hearings, according to a person with knowledge of the matter.
At Justice Merchan’s hearing, the judge is expected to rule on Mr. Trump’s long-shot bid to dismiss the Manhattan criminal case altogether. If he declines to throw out the charges, which stem from a hush-money payment to a porn star in the final stages of the 2016 presidential campaign, he will set a trial date.
Court watchers have been doing calendar calculus, seeking to predict which of Mr. Trump’s cases will come first.
For months, the front-runner seemed to be another case in which Mr. Trump was charged with subverting democracy after the election: the federal indictment brought by a special counsel in Washington.
That case, originally scheduled for March 4, is widely viewed as the most consequential of Mr. Trump’s criminal trials — and perhaps, for him, the most politically problematic. That trial would serve the electorate a steady diet of reminders about Mr. Trump’s worst day as president, when a mob of his supporters stormed the Capitol.
Mr. Bragg, even as he has presented his own case as an instance of Mr. Trump’s interfering with an election, has suggested that he would not object if the Washington case were to go first.
But the Washington trial has been delayed by appeals, and might go before the Supreme Court. The judge in that case, Tanya S. Chutkan, scrapped the March 4 date, leaving the Manhattan trial, which has already been tentatively set for March 25, first on the calendar.
That could still change. As Justice Merchan considers whether to cement the Manhattan date, he is likely to weigh the significance of the Washington case against the uncertainty of its schedule. He and Judge Chutkan have coordinated in the past and they may again this week.
Ultimately, however, the decision is his: If Justice Merchan decides to keep March 25, Mr. Trump’s first criminal trial will be in his hometown.
The case centers on what prosecutors say was Mr. Trump’s effort to hide a potential sex scandal, both before and after the 2016 election. His former fixer, Michael D. Cohen, who is expected to be the star witness in the case and whom Mr. Trump has called a liar, paid the porn star Stormy Daniels $130,000 in the days before voters went to the polls to keep quiet about her story of a tryst with Mr. Trump.
Prosecutors say that once Mr. Trump was elected, he reimbursed Mr. Cohen from the White House, and hid the true purpose of the payments. Mr. Trump’s family business, the Trump Organization, falsely recorded the reimbursements as legal expenses.
The expected ruling from Justice Engoron on Friday will also address accusations of malfeasance at Mr. Trump’s company. Ms. James sued the former president — as well as his adult sons and the family business — accusing them of inflating Mr. Trump’s net worth to obtain favorable treatment from banks and insurance companies.
Even before the trial, the judge ruled that Mr. Trump had acted fraudulently, but on Friday is expected to announce his determination of Ms. James’s remaining claims, including whether the former president conspired with top executives to violate state laws.
He could come down hard on Mr. Trump. Ms. James has asked that the former president be penalized about $370 million and barred from leading any business in the state, including his own.
The decision was originally expected at the end of January but has been delayed. Although the cause of the delay is unclear, there has been a notable amount of post-trial activity in the case. Late last month, a court-appointed official assigned to monitor the Trump Organization issued a report citing what she said were “deficiencies” in its financial reporting. And last week, Justice Engoron questioned lawyers for Mr. Trump about whether a key witness in the case — Mr. Trump’s longtime chief financial officer — had committed perjury.
After some back and forth in emails, the judge made his impatience with the former president’s team clear, potentially a bad omen for Mr. Trump.
“You and your co-counsel,” he wrote to one of the lawyers, “have been questioning my impartiality since the early days of this case, presumably because I sometimes rule against your clients. This whole approach is getting old.”