President Donald Trump pressed then-Secretary of State Rex Tillerson to help persuade the Justice Department to drop a criminal case against an Iranian-Turkish gold trader who was a client of Rudy Giuliani, according to three people familiar with the 2017 meeting in the Oval Office.

Tillerson refused, arguing it would constitute interference in an ongoing investigation of the trader, Reza Zarrab, according to the people. They said other participants in the Oval Office were shocked by the request.

Tillerson immediately repeated his objections to then-Chief of Staff John Kelly in a hallway conversation just outside the Oval Office, emphasizing that the request would be illegal. Neither episode has been previously reported, and all of the people spoke on condition of anonymity due to the sensitivity of the conversations.