A New York federal judge on Thursday threw out President Donald Trump’s challenge to a Manhattan grand jury subpoena for his tax records in a significant blow to the president’s attempt to shield those documents from a state grand jury.

In the 103-page opinion, U.S. District Judge Victor Marrero of the Southern District of New York found for the second time in the case that Trump had not made a showing of immunity from the subpoena. Hearing the case in the wake of a July ruling from the U.S. Supreme Court, Marrero criticized claims of presidential immunity made by Trump’s attorneys.