The smartest person on the field during the Battle of the Bastards in Game of Thrones was Ramsey Bolton. Arguably, he should have won. However, the battle itself was based on a real (and sort of similar) battle in English history, and Jon Snow always had to come out on top.
That meant a brutal fight to the end, and the episode certainly delivered that. At the same time, it showed us how easily Jon Snow was manipulated, with him making several dumb moves from start to finish.
Even the best plan would have been wasted in Game of Thrones
Jon did originally have a decent plan. He wanted to draw Ramsey and his army out, making it possible for Jon's forces to circle around them. While Jon didn’t have the numbers, he had skilled fighters in the form of the Wildlings. However, even the best plan wouldn’t have worked out when Jon immediately acted on emotion.
Sansa warned Jon that Ramsey was manipulative. She had been around him long enough to see how he would make a game out of this battle, and that’s exactly what Ramsey did. The minute Jon saw Rickon on the battlefield, it was clear that Jon would break ranks and run for his brother. And after Rickon was killed, it was clear that he would then charge Ramsey out of revenge.
Jon had always been an emotional fighter. We saw it during the Battle of Castle Black and Hardhome. While he could somewhat turn his emotions off when he needed to, the Battle of the Bastards was never going to be one of those moments. Yet, he should have. Leading an army and acting on emotion is dangerous, and he should have been able to step back and realize exactly what Ramsey was trying to do.
This completely changed the fight, with Jon’s army moving in completely disarrayed. Instead of surrounding Ramsey, they allowed themselves to be surrounded instead. Sure, there is some benefit to chaos, but that’s not what this moment needed. Not up against an organized and loyal force.
The archers and Wun Wun were badly used
Even if Jon hadn’t rushed the battlefield to get to Rickon, there was still a chance that his tactics weren’t going to work. Part of that was due to the badly placed men. The archers were all the way at the back, as part of a strategy that assumed Ramsey’s men would advance.
Now, let’s just remember that Ramsey was smart. He was a sadist, but that doesn’t take away from how smart he was. He planned everything, and he would have seen a simple plan like this a mile off. It’s why he started off by pulling Rickon out and forcing him to run across the battlefield to his death. There was no chance that Ramsey would easily fall for Jon’s obvious tactics so that Jon could make use of the archers.
On top of that, there was the issue of rushing the battlefield. By Jon moving forward and the rest of the Wildlings following him, the archers couldn’t fire. Davos even noted that, making it clear that there was too much risk of harming their own men, and he wasn’t as willing as Ramsey to do that. Ramsey was ruthless, and sometimes, that’s what is needed to be successful in battle — and no, I cannot believe I’ve just agreed with the logic of Ramsey Bolton.
Then there was Wun Wun, who could have been used as something much better than an arrow magnet. We watched how the giants fought at the Battle of Castle Black. While the Wildlings weren’t completely organized, they at least knew how to make use of their strengths, so why wasn't Wun Wun used more effectively? There were a few times he could have helped by being better placed.
It was hard not to feel for Wun Wun at the very end as he battered the doors of Winterfell down, only to finally be felled by arrows. Jon’s actions led to his death, and I don’t think I’ll forgive him for that.
Jon had no idea about Littlefinger’s army
Now, had Jon known that there was another army coming to his aid, things could have been different. I would question a leader willing to let so many people die for a sneak attack to work like Sansa did at the Battle of the Bastards, but it did show some smart planning.
However, Sansa wrote to Littlefinger in secret. She could see how terrible the battle was going to go, and she needed to do something to prevent the complete destruction of Jon and the Wildlings. Had it not been for Sansa’s forethought, there is no way that Jon would have made it out alive, and it just goes to show that Sansa Stark had the best character development of the entire series. She was the smartest of them all, and she deserved to become the Queen of the North.
Jon went into this battle thinking that he had all the men with him. Had he known about Littlefinger’s army, he would have probably wanted them on the field at the same time. It wouldn’t have created the sneak attack that ultimately won the battle.
By the way, this is one part of the Battle of the Bastards that is based on real English history. During the Battle of Bosworth, Henry Tudor went up against King Richard III with a smaller and lesser trained army. He relied on his stepfather’s army to switch sides to fight with him, but nobody really knew what would happen. Had Richard won at the battle, those fighting against him would have been arrested for treason, and that wasn’t a risk everyone was willing to take. Henry’s stepfather only chose his course at the last minute when he saw which side was worth fighting for, supporting the start the Tudor dynasty.
Even then, Henry went into this battle in a dumb way, but at least he thought he could rely on his stepfather. When it came to Jon, he had no idea and rushed head-long into fighting what would have been a losing battle without Littlefinger.
Jon Snow was far more experienced than Henry Tudor was, and he should have known acting on emotion would lead to disaster. He should have also known that going in outnumbered meant a great strategic plan was needed. The Battle of the Bastards proved that Jon wasn’t as effective a leader as he thought he was.
Game of Thrones is available to stream on HBO Max.