Stupidity: When a cop goes to Kevin's house after being requested by police, he simply knocks on the door and after a few seconds walks away assuming no ones home. Had he actually bothered to announce himself as a cop, Kevin would have opened the door and he would have been found safe.
Stupidity: The Engineer and Fireman of the Polar Express train crew should have known better than to not bend back the the metallic prongs of the cotter pin, which would have prevented the cotter pin from coming loose and causing all those problems in the driving of the train.
Stupidity: Hans keeps a major part of his plan secret from his own team: that the electromagnetic lock will be disabled if the FBI shuts down power to the building. The mercenaries hired as muscle don't need to know the minutiae of the plan, but it seems ludicrous that Theo wasn't told. Theo states on more than one occasion that he can't proceed past a certain point and that he hopes Hans has a plan for the final lock. Evidently, Hans was keeping this information secret simply to amuse himself, which makes little sense considering how much planning went into the heist.
Stupidity: After hearing the question on the radio station to win the Turbo Man doll and a failed attempt at the pay phone to answer it, Howard and Myron end up running two blocks to the station to answer the question. This is really stupid because the prize was going to the first caller with the answer and in the few min it would take to run to the station two blocks away and finally reach the DJ, many calls would have come in and most likely someone would have won already, way before the men arrived there.