Jon Snow (Kit Harington) has a lot of talents on Game of Thrones. He can give a rallying speech like no other, summoning people to his side even against their own instincts (and, often, well-being). Swinging a sword comes easy to him. He's one of the few people to ever come back from death without a pair of ice blue eyes, and, according to Ygritte (Rose Leslie), at least, he's a gifted lover, too. Seven hells, he can even ride a dragon now!
What he's not good at, though, is preparing for battle. Which means the north may be in big, big trouble right now.
Let's look back at the evidence presented by Game of Thrones, shall we?
Jon Snow got his first real leadership test during the Battle of Castle Black, and although he was still a nascent brother who kinda got stuck with commanding the forces atop the Wall, it was almost a colossal failure. Sure, the Night's Watch survived the first siege, and he had tried to warn Alliser Thorne (Owen Teale) to seal the tunnel before any of it, but Mance Rayder (Ciarán Hinds)'s men were already positioned to crest another unmanned section of the Wall within hours of falling back. All Jon could hope for was a chance to stab the King Beyond the Wall in the neck to break the spirits of the wildlings and cause them to scatter back to their various factions. Surely, it would've been too late by then, though. If not for the very timely arrival of Stannis Baratheon (Stephen Dillane)'s army, Jon would've been skinned from curls to toenails, and Castle Black would've been toast within a day.
The Massacre at Hardhome was also a disaster for Jon. His pact with Tormund (Kristofer Hivju) to let the wildlings through if they'd join the fight against wights wasn't the problem. Instead it was the fact that rather than distributing the dragonglass to his forces and new friends right away so that they'd have a fighting chance against any walker storm, these essential weapons were left in a bag to burn and/or rot, and the Night King's army grew by the thousands just like [snaps] that. The fact that every guardsman on his side wasn't immediately armed with the only weapons that could save them was a costly oversight on his part.
And let's not forget the hero's welcome he received upon returning home, which — surprise, surprise — spawned from a mutiny he knew was simmering but did not prepare for.
It was the Battle of the Bastards that really showcased his inability to lead the troops in a skirmish, though. To be fair to him, Sansa (Sophie Turner) really should've given him a heads up about summoning the Knights of the Vale — she kept insisting he wait for more men, so sis should've definitely specified that there were more men worth waiting for. However, she also warned him not to fall into one of Ramsay Bolton (Iwan Rheon)'s traps, and by charging all of his forces into the center of the battlefield with no Robb Stark-esque trick plays up his sleeve or even a general awareness of his opponent's own tactics, he did just that. His entire fleet was enveloped from all sides and was quickly becoming one big pile of bodies as the Bolton forces closed in. If not for the horses clashing around him at the beginning, his good luck of being missed by all those arrows in the middle, and the Knights' arrival at the end, he'd be done.
Most recently, his trip north of the Wall also went south. Somehow, he again failed to arm his men with dragonglass, despite having mined plenty in Dragonstone, and he found himself and his team completely surrounded by enemies. Daenerys and her dragons had to travel at lightspeed to come and save them from the Night King's army, and even then he still managed to lose a red priest, a dragon, and Uncle Benjen in the process of securing a wight body which didn't even work to convince Cersei (Lena Headey) to join his side.
Put simply, Jon Snow doesn't know how to lead on a battle. We've seen his field techniques, or lack thereof, fail in four different scenarios — while running defense, during a rescue mission, on offense, and even during a scavenge expedition.
So, what does it mean for the looming battle at Winterfell? Well, he does seem to have learned at least a little from his mistakes, based on the premiere episode. He's brought back plenty of reinforcements, including two dragons, and he appears to be weaponizing his armies well enough with dragonglass rather than let those stores go to waste. However, in the process, he has also bent the knee and lost the confidence of some key northerners — even Lyanna Mormont (Bella Ramsey) has a scowl for him right now — and his own sister, who doubts his true intentions or ability to provide for so many mouths this winter.
We'll have to see whether the fifth time's a charm for Jon Snow in leading his people, all the people of the North, into yet another battle. Unless the show gets even more ridiculous with the deus ex machina, there's no last-minute hero left to swoop in and save him if he makes another mistake. Cersei won't soon march Lannister troops in, the five kings are all dead, and Yara (Gemma Whelan) is now busy trying to win back the Iron Islands with the feeble fleet she has left. So, this is it. His last chance to actually win a big fight, and the stakes have never been higher.
Here's hoping Jon Snow's track record doesn't hold up this time, then, eh?
Game of Thrones airs on Sundays at 9/8c on HBO.