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Two well-known opponents of former President Trump achieved major court wins on Monday when a US judge threw out the federal indictments filed 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, asserting that the administration and DOJ are merely targeting them for retaliation.

US District Judge Cameron Currie tossed the charges in their cases due to attorney Lindsey Halligan's invalid assignment as federal prosecutor. However, she left open the possibility for the federal authorities to refile the case.

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Comey admitted that likelihood after the decision, stating he believes Trump will probably come after him again.

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

But the government confronts significant obstacles to successfully prosecute both after this defeat, and experts are reluctant to forecast what could occur next due to the cases' unprecedented nature.

In my view, it's uncharted territory, said Professor Kay Levine, Emory University School of Law professor.

Could the DOJ challenge the ruling?

The DOJ 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 unfavourable rulings, taking cases from lower courts and sometimes fast-tracking its requests up to the Supreme Court.

Abbe Lowell, an attorney representing James, pledged to continue to challenge any further politically driven indictments through every lawful means available.

In the event of an appeal, the justice department probably would have its own lawyers present the arguments, making Halligan's involvement in the appeal uncertain.

Is it possible there be fresh indictments?

The government accused Comey with making false statements to Congress and obstructing justice. Federal prosecutors charged Letitia James with bank fraud and providing false information to a bank.

Both entered not guilty pleas. In addition to claiming Halligan's appointment was invalid, they also claimed to be targets of vindictive prosecution.

Since the initial charges were dismissed (although appeals might alter this), the DOJ might try to assemble fresh grand juries and obtain new charges.

As far as everything I've seen, a new prosecutor could bring James' case to a new grand jury and get a fresh indictment, stated Ms Levine.

But John Day, head 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 assigned and is able to secure an indictment.

He characterized the complex web of lawyers, courts, and motions involved as a legal quagmire with no simple answers.

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

A key issue is the legal time limit – the deadline that government lawyers had to indict him for these particular claims – which expired at the end of September. However, the indictment's dismissal would activate a half-year extension for the justice department to bring the case again.

Even so in that case, his legal team said it plans to contend the government is past the deadline.

The decision further indicates that since the indictment is invalid, the time limit has run and there can be no further indictment, attorney Patrick Fitzgerald said Monday.

What happens to prosecutor Lindsey Halligan?

In both decisions on the indictments against James and Comey, Judge Currie was blunt: Halligan's appointment was improper.

Judge Currie wrote in the James ruling that the Attorney General's attempt to appoint Ms. Halligan as Acting US Attorney for the Virginia Eastern District was unlawful.

Therefore, she had no lawful authority to present the indictment, the judge wrote.

US attorneys are proposed by the president and need Senate approval. US laws regulate how individuals can be assigned on a interim basis, but Judge Currie found that Halligan's assignment had violated these laws.

This makes Halligan's position on future cases against both individuals, once more, uncertain.

The decision might also cast a shadow on other cases Halligan has prosecuted in the Virginia Eastern District where she works.

But Bondi said on Monday that she made Halligan a special federal prosecutor and commended her work as excellent.

The administration stood by its stance that Halligan was lawfully appointed, spokesperson Karoline Leavitt told the press on Monday.