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Negan with other members of The Saviors ambushed Rick and his small group after they agreed to set camp for the night while they were on their way to The Hilltop to enlist Jesus to help them against The Saviors. After lining everyone up and explaining to them how things were going to be from now on he decided that they should be punished for killing his men and not following his orders. Eventually, Glenn was the unfortunate one to get the short end of the stick.
Negan has a odd but unique personality. He is the leader of a group called saviors, he is feared and respected as a king, but his characteristics cannot be dubbed exactly evil. While he can of course be unmerciful , for instance he killed glen by smashing his brains in with his baseball bat just to simply get a point across, but at the same time he spared both carl for killing his men, and rick as well for attacking him in front of his people. He seems quite reasonable when someone decides to negotiate with him, he was very friendly to carl and had even apologized to him for making him uncomfortable about his condition.
But Despite the fact that he isn't exactly a 'tyrant' and can be quite friendly at times, he still has a habit of provocation and likes to play in power games. He took imminence joy in making rick look like a "B*tch" in front of his people, and had even teased rick about his son, which was the cause of the attack.