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King Mudd
Harry has been found guilty of a multitude of crime like smuggling, transporting stolen goods, possession of illegal substances and man more.  He is a rouge character and swindler but not a violent criminal.  He is along the lines of the two-bit conman.  Harry has had many run-ins with the law and several with the U.S.S. Enterprise and their crew.  
He was once caught trafficking three woman and an illegal substance known as the Venus Drug.  The drug had the ability to make the woman desirable so they could marry rich men.  Harry was eventually caught and sentenced but not for long.
About a year later he got in some trouble with the law and in his quick evacuation he crashed on a planet entirely populated by androids.  He quickly made himself king as the androids were happy to serve.  He started ordering the androids to make more copies.  He even created one of his wife Stella Mudd just so he could enjoy shutting her down.  He soon became extremely unhappy as the android were not much company and lacked many human qualities.
He tried to leave the planet but the androids wouldn't let him so he convinced them that they could divert the U.S.S. Enterprise to their planet and have about 400 people to interact with.  With so many people this would allow Mudd to leave.  The plan worked but Mudd was still not allowed to leave.  So he planed an escape with the Enterprise away team.  The plan was to confuse the androids and force them to shut down.  This worked and allowed the Enterprise to leave but Mudd was forced to stay with a whole series of Stella androids that couldn't be shut down just to keep hin in line.

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