A Deadly State of Mind - S4-E6
Stupidity: In the final scene: Columbo lays a trap for the murderer (George Hamilton). The 'eyewitness' when Hamilton fled the murder scene was a blind man. Hamilton is aware of this. Columbo's gambit depends on Hamilton's assumption that Columbo has coached the witness to act as though he was sighted so as to convince Hamilton that there is evidence against him. In fact, Columbo has the witness' brother, who is sighted, pretend to be the eyewitness and identify Hamilton as the man he saw driving away. When Hamilton falls for Columbo's trap and, believing he is in the presence of the blind man, tries and fails to 'prove' the man can't see. By doing so he reveals his knowledge that the witness was blind, incriminating himself. The problem is, that only a minute or so previously, Columbo had placed Hamilton under arrest, and failed to read him his Miranda Rights. Considering that Hamilton's slip up is the ONLY evidence Columbo has against Hamilton, this was a spectacularly stupid move on Columbo's part. Regardless of how many officers were present to witness this, the fact is that Hamilton was under arrest and had not been advised of his right against self-incrimination; meaning nothing that he said when under arrest can be used against him.
Is Lupin Burning... ?! - S1-E1
Stupidity: Despite the fact that there are 100 (literally) cameras around the racing circuit and (again literally) everyone from the staff to the fellow racers works for the Scorpion gang, Jigen and Lupin's switch can happen without anyone noticing, even if it involved racing side by side for a lengthy period of time.