Let me bring up Dale Kingston. Let's see, kill Uncle Rudy. Drag a naive art student into this with promises of wealth and romance. Trash Uncle Rudy's house. Steal 2 of his paintings. Meet his accessory. Kill her. Fake a car accident. Frame Edna with wrapping paper from Uncle Rudy's house. Frame her with the murder weapon. Finally, plant the stolen paintings in her house to insure this innocent woman's arrest and him becoming the owner of the art collection. All the time sneering at Columbo and manipulating Edna and the family lawyer.
I'll throw in Paul Gerard in "Murder Under Glass".
He manipulated eveybody in sight; blackmailed members of the Restaurant Developers Association; cruelly poisoned one of these members; and even tried to kill off our favourite detective....and of course Columbo hated him!
Let's not forget Paul Galesko (Dick Van Dyke) of "Negative Reaction." It was just not convincing to me that his wife should have been killed, and in addition to that he destroys the life of and frames an ex-convict who was apparently looking to get his life back on the right track.
I think Rip Torn in "Death Hits the Jackpot" was a grade A tossbag. Usually the victims provoke their own murders in some way but this murderer kills his own nephew to steal his lottery winnings.