In the world of criminality, I suspect that the public perception (as on TV) is turned on its head: Whereas criminality is often portrayed as wily and inventive, I think the majority of crooks probably fall into the desperate-dope department.
True. the stock brokers and bankers have got ruses slick enough to quash and elude punishment from the politicians paid to make laws for stock brokers and bankers, but in the wide-screen panorama of crime, wile and guile are more rare than common. For every Bernard Madoff, there are myriad crooks who accidentally leave their driver's licenses at the scene of the crime.
But every once in a while the guile does seem to be true, as for example the case of Neil Moore, who was being held on remand in England, accused of taking almost two million pounds that were not his. Neil, according to a BBC story, apparently got tired of his time waiting behind bars and emailed documents to his jailers that convinced them to let him go on bail. After three days, the ruse was discovered and Moore surrendered, apparently without fuss.
Did he do it just to show that it could be done? I don't know, but the ingenuity appeals to me.