New York Attorney General Letitia James asked a judge Tuesday to sanction Donald Trump, his sons, and their lawyers for reusing their failed legal arguments in a $250 million civil fraud lawsuit against the former president and his business. Prosecutors in James’ office argued that “sophisticated defense counsel should have known better” than to rehash “previously rejected arguments” as they attempt to battle the suit. The filing claims there have been at least five separate instances since last October in which Trump’s legal team have submitted the same legal arguments. Three of those arguments have already been rejected in court, while two—filed more recently—haven’t yet been ruled on. James’ office, noting that a judge has the ability to “impose financial sanctions upon any party or attorney in a civil action or proceeding who engages in frivolous conduct,” requested that Trump’s lawyers be fined a collective $10,000, and their clients another collective $10,000. Despite Trump’s repeated attempts to have the case thrown out, the trial is set to kick off on Oct. 2.