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A pair of well-known opponents of President Trump secured significant court wins on Monday when a US judge dismissed the federal indictments against them.

For weeks following their charges, ex-FBI chief James Comey and NY AG Letitia James have insisted fiercely that they are not guilty, claiming that the administration and DOJ are simply singling out them for retaliation.

US District Judge Cameron Currie tossed the charges in their cases due to prosecutor Lindsey Halligan's invalid assignment as federal prosecutor. But she also left open the possibility for the government to try again.

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Comey acknowledged that possibility after the ruling, stating he thinks Trump is likely to come after him again.

And White House spokesperson Abigail Jackson seemed to confirm it: This will not be the last chapter on this matter.

But the DOJ faces steep hurdles to successfully prosecute either after this defeat, and legal analysts are reluctant to forecast what could happen next due to the unprecedented circumstances of the cases.

It feels to me like uncharted territory, stated Kay Levine, law professor at Emory University.

Could the justice department challenge the ruling?

The Department of Justice can contest Judge Currie's ruling before a federal appeals court. In this case, that would be the Fourth Circuit Court of Appeals.

Attorney General Pam Bondi signaled she would take this route, pledging to use all available legal action, including an immediate appeal.

Previously, the Trump administration has strongly challenged adverse decisions, taking cases from trial courts and sometimes fast-tracking its requests up to the US Supreme Court.

Attorney Abbe Lowell, James's lawyer, vowed to keep fighting any further politically motivated charges through all legal avenues.

In the event of an appeals process, the justice department probably would have its own attorneys argue the case, making Halligan's role in the appeal unclear.

Is it possible there be fresh indictments?

The government charged Comey with lying to Congress and obstruction of justice. Federal prosecutors charged Letitia James with bank fraud and making false statements to a financial institution.

Each pleaded not guilty. In addition to arguing Halligan was unlawfully appointed, they also asserted to be victims of vindictive prosecution.

Since the initial charges were dismissed (though, of course, appeals could change that), the government might try to convene new grand juries and secure new indictments.

Based on my analysis, a new prosecutor could bring James' case to a different grand jury and secure a new indictment, stated Ms Levine.

But legal expert John Day, president of the American College of Trial Lawyers, said it could be a complex process – certainly in the Comey matter.

It's clear that it will be hotly contested, whether Comey's case can be re-indicted if a lawfully appointed prosecutor is appointed and is can obtain an charge.

He characterized the tangle of lawyers, courts, and motions involved as a procedural morass with no easy solutions.

It could be harder for the DOJ to try to bring the exact same charges against James Comey.

One problem is the statute of limitations – the deadline that government lawyers had to charge him for these particular claims – which expired at the close of September. However, the indictment's dismissal would activate a six-month grace period for the justice department to refile the case.

Still in that situation, his lawyers said it plans to argue the prosecution is past the deadline.

The ruling also suggests that since the indictment is void, the statute of limitations has run and there can be no new indictment, attorney Patrick Fitzgerald said on Monday.

What happens to Lindsey Halligan?

In both decisions on the indictments against James and Comey, the judge was direct: Halligan was wrongly appointed.

The judge stated in the James decision that the Attorney General's attempt to install Halligan as Interim US Attorney for the Eastern District of Virginia was invalid.

As a result, Halligan lacked legal power to present the indictment, the judge wrote.

Federal prosecutors are proposed by the US president and require Senate approval. Federal statutes govern how individuals can be appointed on a interim basis, but the judge determined that Halligan's assignment had breached these regulations.

That leaves Halligan's position on subsequent cases against both individuals, again, unclear.

The ruling also could raise doubts on other cases Halligan has prosecuted in the Virginia Eastern District where she works.

But Attorney General Bondi said on Monday that she designated Halligan a special US attorney and praised her work as excellent.

The White House stood by its stance that Halligan's appointment was legal, spokesperson Karoline Leavitt told the press on Monday.