1. Rick Kills Winslow
The most brutal walker kill on The Walking Dead up through season 7 has to be Rick killing Winslow in the “New Best Friends” episode. Winslow, the armored walker belonging to The Scavengers, is the most horrifying and dangerous walker seen so far. Covered in spikey armor and with a helmet keeping him safe from the only thing that could actually kill him Winslow seems unbeatable.
Rick got one of Winslow’s spikes through his hand when he tried to keep Winslow at a distance. He quickly realized that he couldn’t kill Winslow through any of the usual methods because the helmet protecting his brain meant that Rick couldn’t cause enough serious head trauma to kill him.
At Michonne’s suggestion he used garbage and other items from the walls of the makeshift ring to pin Winslow to the ground. Then he used some broken glass that he found in one of the piles to cut off Winslow’s head. Ultimately Rick beat Winslow but it was one heck of a fight. And no one was really sure who would win.
Beating Winslow got Rick what he wanted – the cooperation of The Scavengers in the fight against Negan and The Saviors. But taking Winslow down was definitely one of the most brutal walker kills if not the most brutal walker kill on The Walking Dead.