Jack Smith's extremely aggressive prosecution of Donald Trump may have crossed a "red line," setting Smith up for failure at trial.

Smith plans to use cellphone data he seized from Trump to walk the jury through his alleged crimes on January 6th.

But the audacious move may backfire by introducing more complications to the case, which is already facing delays.

Smith crosses the line...

Mike Davis, founder of the Article III project, said Smith's seizure of data "crosses a red line" by undermining executive privilege.

“This sets a destructive precedent for the presidency, as it seriously undermines the president’s ability to get his constitutionally protected, confidential and candid advice from his advisers,” he said.

Smith is leaning on a Supreme Court ruling against President Nixon to argue that executive privilege does not apply to Trump here. But it's not clear that courts will want to take it that far, conservative law professor Jonathan Turley said.

“The phone records may add to the unease of some judges and justices over the fight over presidential immunities and privileges," Turley said.

“However, Smith has the Nixon case to cite for such demands in the investigation of possible criminal acts. What is clear is that the Court may be pushed into a major line-drawing decision over inherent presidential immunities,” he said.

Trial in doubt...

Trump's lawyers argue he is constitutionally immune to Smith's charges for "overturning" the 2020 election because he was following his official duties.

Smith has pushed back, arguing that standard would place presidents above the law. Smith is taking such an aggressive tack, he wants to stop Trump from even speculating to the jury that Joe Biden is connected to the trial, despite the obvious politics of the case.

Smith has made it clear that he wants the thorny and unprecedented issues raised by his case to be resolved ASAP, so he can get a quick conviction before the election arrives. But the more complicated the case gets, the less likely it will go to trial on the schedule Smith wants.

The Supreme Court last month shot down his vague concerns about the "public interest" in speeding things up, raising the possibility that Trump will run out the clock through the appeals process.

Regardless of how things play out, one thing is clear: Smith is taking the country into dangerously uncharted territory.