Two cases. Two judges. A high-risk week for Trump.

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

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

The next day, according to two people with knowledge of the matter, the second judge is expected to issue a ruling that threatens not 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 Trump hundreds of millions of dollars and separate him from the company he ran for decades.

The double threats represent a turning point in Trump's legal odyssey, a week that could reshape his personal and presidential fortunes as he marches toward the Republican nomination. Judge Engoron's ruling could drain Trump's coffers, and if the former president ultimately leaves Judge Merchan's courtroom as a criminal, he would send the country's already bitter politics into uncharted realms.

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

But Trump's week in New York 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 five years for the district attorney's office to file an indictment. But both cases have worked their way through the legal system to become immediate threats to the former president, and at an inopportune time.

Their legal imbroglio, of course, doesn't end in New York. Trump faces 91 felony charges in four criminal cases, in Washington, Florida and Georgia, as well as in Manhattan. On the civil front, he must deal with Judge Engoron's fraud ruling and the $83.3 million he owes in a recent defamation case.

Thursday will be especially hectic. On the same day, and at the same time that Judge Merchan is expected to rule, the Georgia prosecutor who accused Trump of conspiring to overturn the 2020 election will face a hearing into his romantic relationship with a lawyer he hired to work on that decision. 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.

At Judge Merchan's hearing, the judge is expected to rule on Trump's risky attempt to dismiss the Manhattan criminal case entirely. If he refuses to dismiss the charges, which stem from a hush 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 calculations, trying to predict which of Trump's cases will come first.

For months, the frontrunner appeared to be another case in which Trump was accused of subverting democracy after the election: the federal indictment brought by a special prosecutor in Washington.

That case, originally scheduled for March 4, is widely considered the most consequential of Trump's criminal trials and perhaps, for him, the most politically problematic. That trial would serve voters a steady diet of reminders about Trump's worst day as president, when a mob of his supporters stormed the Capitol.

Bragg, even as he has held up his own case as an example of Trump interference in an election, has suggested that he would not object if Washington's case were the first to be addressed.

But the trial in Washington has been delayed by appeals and could go before the Supreme Court. The judge in that case, Tanya S. Chutkan, vacated the March 4 date, leaving the Manhattan trial, which had already been tentatively set for March 25, at the top of the calendar.

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

Ultimately, however, the decision is his: If Judge Merchan decides to keep March 25, Trump's first criminal trial will be in his hometown.

The case centers on what prosecutors say was Trump's effort to conceal a possible sex scandal, both before and after the 2016 election. His former fixer, Michael D. Cohen, is expected to be the case's star witness. and whom Trump has called a liar, paid porn star Stormy Daniels $130,000 in the days before voters went to the polls to keep quiet about her story of a date with Trump.

Prosecutors say that once Trump was elected, he repaid Cohen from the White House and concealed the true purpose of the payments. Trump's family business, the Trump Organization, falsely recorded the refunds as legal expenses.

Judge Engoron's expected ruling on Friday will also address allegations of misconduct at Trump's company. James sued the former president, as well as his adult children and the family business, accusing them of inflating Trump's net worth to obtain favorable treatment from banks and insurance companies.

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

He could be tough on Trump. Ms. James has called for the former president to be penalized about $370 million and banned from running any business in the state, including his own.

The decision was initially expected to be made at the end of January, but was 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 her financial reporting. And last week, Judge Engoron questioned Trump's lawyers about whether a key witness in the case – Trump's veteran financial director – had committed perjury.

After some email exchanges, the judge made clear his impatience with the former president's team, which could bode poorly for Trump.

“You and your co-counsel,” he wrote to one of the attorneys, “have been questioning my impartiality since the early days of this case, presumably because I sometimes rule against your clients. “This whole approach is becoming obsolete.”



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