Michael Flynn, the former national security adviser for President Donald Trump, is expected to plead guilty on Friday to lying to federal investigators about his interactions with a Russian official after the 2016 election.

Flynn’s confession to having committed a federal crime comes with a special degree of irony, as he was one of the most prominent Trump supporters to lead a “lock her up” chant calling for Hillary Clinton’s imprisonment. “If I did a tenth of what she did, I would be in jail today,” he declared at the Republican National Convention in July 2016.

Clinton has never been charged with a federal crime. Here are five times Flynn accused her deceiving the public and leading a chant to “lock her up.”