The Night of the Human Trigger - S1-E12
Stupidity: West and Gordon are in the coal cart and rock it until it tips over so they can escape. Neither West nor Gordon had their feet tied up, only their wrists, meaning both could have merely stood up in the cart and jumped out of it, rather than rocking it side to side.
Stupidity: Being a U.S. government-owned Secret Service vehicle, West and Gordon's train, "The Wanderer" is woefully lacking in security, as everyone from uninvited strange women to villains are allowed to just walk through the door of West and Gordon's private train car.
The Night of the Firebrand - S3-E2
Stupidity: West is introduced to, then knocked unconscious by Vixen as she hides a club behind her back. A trained Secret Service agent like West would not have let his guard down in this situation, as the entire fort was awash in bad guys.