Originally Posted by DashTrash508

STATE v. HICKMAN | FindLaw

This is just one case from the early 2000s. At one point, there were more than 40 employees of Northwest Airlines under investigation or indictment for tax evasion in Minnesota. I cannot speak to the other poster's personal connection to anyone in tax trouble for similar circumstances, but there are plenty of cases out there regarding airline pilots and tax evasion. Bottom line, get professional advice, try it if you want, but be prepared to face the music if an overzealous auditor decides to come after you.