Former President Donald Trump raised eyebrows this weekend when he all but dared the judge in charge of his New York hush-money case to lock him up for violating a gag order.

Yet that isn't the only one of Trump's cases to make headlines, as one observer says that Special Counsel Jack Smith is "at a breaking point" with federal Judge Aileen Cannon. 

Smith and Cannon clash over jury instruction

Smith is prosecuting Trump in Florida over the former president's retention of classified documents after leaving the White House.

According to MSNBC legal blog writer Jordan Rubin, Smith is concerned that Cannon "will use wacky jury instructions that could tank" his efforts.

At issue is Cannon's request that Smith's team and Trump's defense attorneys each submit sets of hypothetical jury instructions.

Fox News reported Cannon asked that the proposed instructions address scenarios in which she accepted Trump's argument that the Presidential Records Act (PRA) justified his conduct.

The network noted that Smith responded by filing a brief in which he complained that the judge is operating on a "fundamentally flawed legal premise" since the PRA "should not play any role at trial at all."

Smith may try to have judge removed from case

"The PRA's distinction between personal and presidential records has no bearing on whether a former President’s possession of documents containing national defense information is authorized under the Espionage Act, and the PRA should play no role in the jury instructions on the elements of Section 793," Fox News quoted the brief as stating.

Smith went on to assert that should the judge go ahead with her jury instructions order then he plans to file an appeal.

Meanwhile, The Hill reported that former Trump White House attorney Ty Cobb told CNN he believes Smith may succeed at getting Cannon removed from the case.

Expert says Smith seems "to be daring Smith"

"I think that Jack Smith — I think the filing today makes it plain that she has to rule, and if she doesn’t rule under either scenario, they'll be in a position to take her up to the 11th Circuit," The Hill quoted Cobb as saying.

Cobb is not alone in that assessment, as Palm Beach County State Attorney David Aronberg told NBC News that Smith "is close to pushing the nuclear button."

However, Aronberg also pointed to a filing from Cannon on Thursday in which she seemed "to be daring Smith" to try and remove her.