Figured a good place to start IOTW is Iman Shumpert.
The former NBA guard, who won a championship with Cleveland and also won Dancing With The Stars, has an estimated career earnings at $50 million. Married to pop sensation Teyana Taylor (in Denver 8/10, get your tickets at live nation before they sell out), he is also a recording artist. His album "Substance Abuse" includes lyrics such as, "elevators get stuck, won't let me down".
Mr. Shumpert attempted to board a plane in Dallas while carrying 6.12 ounces of marijuana. Also found in his bag was a magazine for a Glock handgun, containing 14 rounds of live ammunition.
The police report says Shumpert, "asked if there was any way he could make his flight" to Los Angeles, where he was supposed to pick up his daughter, but the responding officer informed him he would not be making that flight, as he was being placed under arrest for marijuana possession.
I hereby nominate Iman Shumpert as IOTW.