Two cases. Two judges. One high-stakes week for Trump.

In two courthouses two blocks apart, two New York judges could ruin Donald J. Trump's week.

On Thursday, one of the judges, Juan M. Merchan, may schedule the first criminal trial of a former US president as early as next month, raising the specter that Trump could end up behind bars.

The second judge is expected to issue a ruling the next day that will endanger not Trump's freedom but his family business, according to two people with knowledge of the case. The judge, Arthur F. Engoron, oversaw the former president's civil fraud trial and is weighing the New York attorney general's request to punish Trump hundreds of millions of dollars and cut him loose from the company he owned for decades led.

The twin threats mark a turning point in Trump's legal odyssey, a week that could reshape his personal and presidential fortunes as he moves toward the Republican nomination. Judge Engoron's ruling could drain Trump's coffers, and if the former president ultimately walks out of Judge Merchan's courtroom as a felon, it would send the country's already bitter politics into uncharted territory.

Trump has used the New York cases to falsely portray himself as a victim of a Democratic cabal bent on persecuting him and helping his presumptive general election opponent, President Biden. And he has repeatedly attacked the two Democrats who brought the cases — Manhattan District Attorney Alvin L. Bragg, who filed the criminal charges, and New York Attorney General Letitia James, who led the fraud case.

But Trump's week in New York underlines the limitations of one of his proven legal strategies: delays. Ms. James had to litigate for two years before she could file her lawsuit, and it took the district attorney five years to file charges. But both cases have worked their way through the legal system and become an imminent threat to the former president, and at an inopportune time.

Of course, his legal confusion doesn't stop in New York. Mr. Trump faces 91 felony charges in four criminal cases in Washington, Florida and Georgia as well as in Manhattan. On a civil level, he is dealing with Judge Engoron's fraud ruling and the $83.3 million he is owed from a recent defamation case.

Thursday will be particularly hectic. On the same day, and at the same hour that Judge 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 has hired to work on it. case. As of Monday morning, Trump was still discussing whether he would attend one of the hearings, according to a person with knowledge of the matter.

During Judge Merchan's hearing, the judge is expected to rule on Trump's long-awaited bid to dismiss the Manhattan criminal case entirely. If he refuses to dismiss 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 running calendar calculations, trying to predict which of Trump's cases will come first.

For months, the frontrunner seemed to be another case accusing Mr. Trump of undermining democracy after the election: the federal indictment filed by a special prosecutor in Washington.

That case, originally scheduled for March 4, is widely seen as the most consequential of Trump's criminal trials — and perhaps, for him, the most politically problematic. That process would provide the electorate with a steady diet of memories of 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 example of Mr Trump's interference in elections, has suggested he would not object if the Washington case were heard first.

But the Washington trial has been delayed by appeals and could end up before the Supreme Court. The judge in that case, Tanya S. Chutkan, canceled the March 4 date, putting the Manhattan trial, which had already been tentatively set for March 25, first on the calendar.

That could still change. As Judge Merchan considers whether to set the date in Manhattan, he will likely weigh the significance of the Washington case against the uncertainty of its scheduling. He and Judge Chutkan have coordinated in the past and will do so again this week.

Ultimately, though, it's his decision: If Judge Merchan decides to keep March 25, Trump's first criminal trial will take place in his hometown.

The case centers on what prosecutors say was Trump's attempt to cover up a potential sex scandal both before and after the 2016 election. His former fixer, Michael D. Cohen, who is expected to be the key witness in the case and whom Mr. Trump has called a liar, paid porn star Stormy Daniels $130,000 to remain silent in the days before voters went to the polls. her story of a tryst with Mr. Trump.

Prosecutors say that after Mr. Trump was elected, he reimbursed Mr. Cohen from the White House and concealed the true purpose of the payments. Mr. Trump's family business, the Trump Organization, incorrectly recorded the fees as legal fees.

Judge Engoron's expected ruling on Friday will also address allegations 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 gain favorable treatment from banks and insurance companies.

Even before the trial, the judge ruled that Mr. Trump had acted fraudulently, but is expected to announce his decision on Friday on Ms. James' remaining claims, including whether the former president conspired with top executives to violate state laws.

He could come down hard on Trump. Ms. James has asked that the former president be sentenced to about $370 million and banned from running any business in the state, including his own.

The decision was originally expected at the end of January, but has been postponed. Although the cause of the delay is unclear, there has been a lot of activity in the case since the trial. Late last month, a court-appointed official charged with overseeing the Trump Organization released a report citing what it said were “deficiencies” in its financial reporting. And last week, Judge Engoron questioned Mr. Trump's lawyers about whether a key witness in the case — Mr. Trump's former chief financial officer — had committed perjury.

After some back-and-forth, the judge made clear his impatience with the former president's team, which may have boded ill for Mr. Trump.

“You and your co-counsel,” he wrote to one of the attorneys, “have questioned my impartiality since the beginning of this case, presumably because I sometimes wrong your clients. This whole approach is getting old.”