I run an aircraft charter operation.
We use the same no fly list. Except, if the aircraft has a gross take off weight of less than 12,500 pounds, we don’t have to check passengers against the no fly list.
So yes, he could charter, but coming out of Hawaii he’s going to need a large private jet, like a Gulfstream, (about $6,000 per flight hour) which is well over 12,500 pounds.