The collision between November’s presidential election and Trump’s extraordinary tangle of legal liabilities, trials, court appeals and tests of the rule of law is deepening as he tightens his grip on the Republican nomination. Several civil cases are moving toward their conclusions, with painful financial consequences  for the ex-president. But there are growing signs that his delaying strategy, designed to postpone full accountability until after the election, could be working on several criminal fronts. And the nation’s top judges and justices are now wrestling with the consequences of Trump’s attempts to strain the guardrails of the political system to their limits. The resulting precedents will echo for as long as America remains a republic.

Trump, his lawyers, his political opponents and constitutional scholars are braced for huge looming developments.

— On Thursday, the Supreme Court will hear oral arguments over a decision by the Colorado Supreme Court to throw Trump off the ballot under the 14th Amendment’s ban on insurrectionists. This follows the mob attack by his supporters on January 6, 2021, incited by his false claims of electoral fraud in 2020. The case has profound importance to the 2024 election and for how future elections will unfold. The Supreme Court had little choice but to step in because differing legal rulings between several states threaten to cause national electoral chaos over Trump’s eligibility on state ballots. Maine has take a similar step to Colorado but that case hasn’t yet reached the US Supreme Court. The Colorado case was initially seen as a long shot to go against Trump, but a flurry of briefs to the Supreme Court from historians and legal scholars show that it will not be easy for the justices to punt with a novel ruling that dismisses the issue out of hand. Key are whether the Civil War-era amendment applies to presidents and whether it is self-executing or would require a court or Congress to rule on insurrection adjudications. Trump’s supporters are using the case to rebut his critics’ claims that he’s a threat to democracy, arguing that throwing him off the ballot is a direct affront to voters and an example of election interference.

— Another huge constitutional question is in limbo pending a ruling from a federal appeals court in Washington, DC, into Trump’s sweeping claim of presidential immunity, which he argues shields him from prosecution over his attempts to overturn the 2020 election. The ruling could decide whether special counsel Jack Smith’s federal election interference case goes ahead before the election. More broadly, Trump’s calls for unlimited presidential power have huge implications for how he might behave in a second term and transform the reach of the presidency itself.

— Trump is braced for a ruling in a civil fraud trial in New York targeting himself, his adult sons and the Trump Organization. Judge Arthur Engoron has already said that repeated fraud took place. His final ruling, expected within days, centers on issues including how much Trump will have to pay for ill-gotten gains and whether he will be barred from doing business in the state where he made his name. A judgment that runs into several hundred million dollars could put significant strain on Trump’s cash reserves and wealth.