Being in a damn cell , bouncing a ball is entertaining now? If he was going to “swindle” his way to the top of the food chain he would have done it when they were at there most vulnerable when Rick was reported dead and Michonne having the baby. That was when he had his chance. Now he has no chance with was stupid. As for him taking years to get to top of another group. How u figure?
If he ran into Magna group , he is the instant leader.
Meet the whispers and he is middle manager off the rip.
Doesn't work like that though. With Rick reported Dead, and Michonne having the baby, EVERYONE would be behind Michonne, if based on sympathy alone. She could've said off with his head and everyone would be game. And he'd also have no one on his side, but instead a list of people vying for one spot.
The long con is in the waiting game. After this amount of time in TWD universe, any group he runs into with these level of resources, has some sort of civilized order, some chain of command, something that makes their system work. He can't go muscling his way in, not if he wants people behind him and not have to challenge every i-want-that-spot. He has to watch, learn, charm his way into leadership. He's been comfortable in Alexandria long enough, gaining info, learning how everyone thinks and how to push buttons and nudge.
The only thing I would say is that whatever happened between Alexandria, Hilltop & Kingdom, he probably had a chance then...but any wise person waits until after the dust settles and sees what he has left to deal with.