The Walking Dead Episode 15 saw many groups preparing to mobilize; Rick and Co. went to procure guns in their build up to fighting Negan, the Big Bad himself revealed his plan to travel to Alexandria the following day and even Gregory seemed to be planning a little trip of his own. But while Rick and Negan's intentions were clear — they're basically out for each other's blood — what was a little murkier was where exactly Gregory was going and what his plan was.
The last we saw of Gregory in Episode 15, he was pouring over a map of Virginia and telling Kal to pack his bag for an overnight trip. With this scene coming directly after the scene with Negan chatting to Sasha about his "little birdie" informant, you'd be forgiven for thinking that he was headed towards Negan's main base, but in reality it's more likely he's on his way to see Simon.
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You might remember that back in Episode 14, Gregory voiced his concern to Simon over the matter of someone with "crazy ideas," and who is less cooperative taking over Hilltop. In response, Simon wrote down the directions to his base, and told Gregory to visit him if he ever had issues with someone else making a bid for leadership. We actually saw this slip of paper make a reappearance in Episode 15, just before Gregory opened the map.
After Maggie not only demonstrated her intelligence by educating the community on how to plant crops that would last for years to come, but also her physical prowess - taking out walkers with ease when compared to Gregory - it seems that she's become too much of a threat for his liking, hence the trip.
However, now that we know where Gregory is headed, the question remains of what exactly he intends to do once he gets there. Fingers crossed he proves as useless as being a traitor as he is as being a leader!
The Walking Dead returns to AMC with Episode 16 on April 2