Lil Wayne is facing a federal weapons charge from an incident in Miami, December 2019. He raised a few eyebrows in November 2020 when he publicly endorsed Trump for re-election and posed with the embattled president at the White House. Wayne struck a plea deal with the feds and agreed to pleade guilty to illegally possessing the weapon but still faces prison, if convicted. Before Trump goes, he reportedly plans on pardoning Lil Wayne along with up to 100 other people on his last full day in office.