Two Cases. Two Judges. One High-Stakes Week for Trump.

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.