People are hoping for a plot by the northern houses to take back Winterfell, but the hope that something is brewing isn’t a defacto assumption that Ramsay is stupid.

People are hoping Jon somehow manages to rally the North to his cause as a bastard son with no legit claim to Winterfell…. In alliance with the Wildlings after kinda-sorta violating his oath to the Watch. That’s a tall order even with the support of Sansa.

Again, I don’t see where anyone assumes Ramsay is stupid. People are simply hoping the other northern houses have something in the works.
I’m not seeing the dots connect to Ramsay being stupid.

What I will say is that Ramsay’s rise through such ruthless means actually illustrates a coming moment of weakness. He’s smart but we’ve seen nothing in the show that shows him to be a brilliant tactician or politician. He’s a spoiled, privileged brat who was given some power by his father and took greater power in a moment of opportunity, not through some brilliant strategy.

Conversely, Jon is as seasoned as anyone in the show. In fact I’m struggling to think of anyone alive at this point with better credentials to take out Ramsay. Add the fact that the North has historically shown great loyalty to the Starks and you don’t need to take Ramsay for a fool to believe Jon can win this fight.