Two of President Trump’s historic legal proceedings will coincide Monday as his $454 million civil fine comes due and his hush money criminal trial enters the next phase. Mr. Trump’s real estate empire and his personal freedom will both be at stake just as the general election kicks off.

Monday could be the beginning of the end for the former president’s vast real estate portfolio, which helped launch his brand as a master dealmaker and ultimately led to his election to the presidency. Mr. Trump has so far been unable to secure a bond for his civil fine, announcing in a legal filing that he had contacted more than 30 firms in search for the money, but was ultimately unsuccessful. 

The New York attorney general, Letitia James, has made it clear that she intends to seize some of Mr. Trump’s properties in order to help settle the nearly half-billion dollar civil fine. 

Mr. Trump is appealing the decision from Judge Arthur Engoron that found he had persistently engaged in fraud over the years in order to win more favorable loan and tax rates for his properties. Another judge denied Mr. Trump’s request for reprieve from posting the bond while he appeals Judge Engoron’s decision. 

“If he does not have funds to pay off the judgment, then we will seek judgment enforcement mechanisms in court, and we will ask the judge to seize his assets,” Ms. James told ABC News in an interview in February. 

Some of the properties Ms. James could seize include Mr. Trump’s golf club just north of New York City and the famous Manhattan tower that bears his name. A legal filing last week from Ms. James in the Westchester County Clerk’s office could signal that the golf course could be first to fall out of Mr. Trump’s real estate empire. 

Losing a few properties to the state of New York could be the least of his troubles, however. On Monday morning, Mr. Trump will appear in a Manhattan courtroom alongside his defense team and prosecutors from the Manhattan district attorney’s office to begin the next phase of his criminal trial. Judge Juan Merchan is expected to officially schedule the criminal trial for late spring or early summer. 

The criminal proceeding against Mr. Trump has been stifled by delays from district attorney Alvin Bragg, who recently sent the former president’s defense team more than 10,000 pages of documents related to the prosecution. Those documents were produced to Mr. Bragg by prosecutors at the Southern District of New York who won a conviction against Mr. Trump’s former fixer, Michael Cohen, who paid $130,000 to the adult film star Stormy Daniels just days before the 2016 presidential election. 

The trial was originally set to begin Monday, but Judge Merchan has delayed the proceedings until at least late April. On Monday, the jurist could delay the trial even further depending on the arguments made by both the prosecution and defense. 

Mr. Trump is accused in that case of knowingly perpetrating a hush money scheme to Stormy Daniels, whose real name is Stephanie Clifford. If convicted, he could face up to four years in state prison. 

Mr. Trump’s legal team has argued that the case should be dismissed on the grounds that Ms. Clifford is attempting to poison the jury pool by releasing a documentary just days before the Monday court appearance. They call the release of the documentary “unacceptable” and “prejudicial.”
During a screening of Ms. Clifford’s documentary, fans from New York showed up to support the “queen of resilience,” as one attendee described her to the Sun.