Arthur Blackwood, also known as the Crusader in Marvel Comics, experiences doubts about the righteousness of his cause primarily when he faces defeat. One notable instance is when Luke Cage defeats him by breaking his sword. This loss significantly undermines Blackwood's confidence in his mission, causing him to question the validity and righteousness of his crusade.
For more detailed information, you can refer to the Marvel Database entry on Arthur Blackwood (Earth-616) here.