According to The Walking Dead Books, Gregory Is Not Long For This World

One of The Walking Dead's most vile men happens to be the leader, well, former leader of the Hilltop Colony: Sir Gregory. He unapologetically sheds his snakeskin every chance he gets and manages to float his way through the zombie apocalypse. In season eight, Gregory becomes a valuable asset for Negan, but not so much for his people at the Hilltop — especially after sticking his nose in the bullet-riddled war against Alexandria Safe-Zone and The Kingdom.

It's been established that almost no one will shed a tear if Gregory loses his life. Yet, he's so cunning that he wins his way back into the Hilltop, under Maggie's orders, after he betrays Rick and King Ezekiel at The Sanctuary and pledges allegiance to the Saviors. We still, however, haven't gotten much background on Gregory. There isn't a ton of information on whether he came from humble beginnings pre-apocalypse. What we do know is that his time will come to an end, if the show follows Robert Kirkman's comic book series.

Gregory's demise plays out appropriately in the books, and he's the one ultimately responsible for the way it goes down. He makes a failed attempt on Maggie's life after his cup of jealousy runeth over, which results in his own execution right on the property he had once run with a frail fist. Kirkman's version details that it's the nuisance, Morton, who plants the seed to kill Maggie.

Gregory invites Maggie inside his trailer to talk about plans and deviously serves her poisoned wine in hopes of killing her. Jesus witnesses Gregory gloating over a poisoned Maggie on the floor and kicks him out of the way to rush to Maggie's side. Even while she could've been dying, Maggie tells Jesus not to kill him but to put him in jail instead.

In typical Gregory fashion, he relentlessly protests his incarceration. What he doesn't realize is that the appointed community physician, Harlan Carson, notices that the drugs stolen from his offices are also in Gregory's trailer where Maggie had been poisoned. After some persuasion by Jesus and Tammy Rose, Maggie came to the conclusion that the only way to guarantee the safety of herself and the people of the Hilltop is to kill Gregory, and he was sentenced to death by hanging from a tree.

Stay tuned to see if this is how he goes out on AMC's version.