@Drew007 said:

Then the next time we see him, he is with Negan. So what happened to the people that went with Dwight? They did kind of a time jump there.

I was thinking the same thing. I thought the deal was Dwight would stay with them, and would radio back to Negan that all was well after the ambush. Rick just let him head off in a car by himself? I would have had him in handcuffs and a guard on him until the fight was over and Negan was dead.