A federal judge overseeing the criminal case against Roger Stone, a longtime ally to President Donald Trump, appeared skeptical of his efforts Thursday to get the charges tossed.

The Republican operative and his legal team were in a Washington federal courtroom offering up a menu of creative constitutional arguments to challenge the indictment. Stone was indicted in January on charges that he lied to a congressional committee and attempted to obstruct its investigation into Russian interference in the 2016 U.S. election.