friends turned enemies turned ???

So, read through this, and not gonna lie, all of it is right up Jerry's ally in terms of turning Dream Walkers into Shades like himself. He likes to play with his targets emotionally and mentally; basically just really get to know them, before he uses the knowledge and trust he's gained from them to tear them down.

Someone like Cheyenne is exactly the kind of person Jerry would target - most likely because Cheyenne reminds him a little bit of Jerry's prior self. Desiring companionship, eager to make friends, a generally happy-go-lucky sort in the dream world, but sad and lonely during their waking hours, they would've been two peas in a pod had Jerry not been a monster.

It was just meant to be in the worst kind of ways.

Of course, now that Jerry's gotten what he wanted via twisting Cheyenne into a Shade, the fun for him doesn't actually stop there. Now with Cheyenne on his "level" - so to speak - Jerry would just rub it in like a really arrogant winner. Popping up unannounced to pester him with a cheshire grin whilst asking things like "So, how many fell for it just like you today, Cheyenne?"  Trying to almost turn making Shades into a competition between them.  In a sense, after making Cheyenne a Shade, Jerry's true colors would start to bleed through and he'd still try to act buddy buddy with him in the worst kind of ways.  It's almost like Jerry's just flat out mocking him in this passive subtle banter.

Then the fact that Jerry knows Cheyenne like the back of his hand, while the other is forgetting everything about himself, would only add fuel to this blazing fire Jerry's set. Jerry would probably hold this fact over Cheyenne's head as well, even toy with him by giving him vague information and hints about his past like...

"I wonder if your dog's okay."
"... What are you talking about?"
"Your dog."
"I never had a dog."
"Wow, you talk about this dog to me all the time, going on and on about how cute it is and now I want to talk about it and you can't even remember the fact you had him in the first place?  Rude."
"... What, but I--"
"...  Or maybe it was a cat.  Nah, you look like the goldfish type.  Especially with that memory of your's.  I'm calling you Dory now."

Cheyenne trying to guess about the details of his life and Jerry's just no help despite the fact he knows everything. It's all just part of the fun to him. He's like a nasty older brother that doesn't know when all of his teasing and taunting is not funny anymore. I can see their dynamic definitely being brotherly in nature, but it's that tense I fucking hate you, but you're like one of the few people I can talk to kind of situations.

However, Jerry is plotted to have an eventual redemption through his own best friend, Lucas Courtwater, which adds an interesting twist to this because after Jerry becomes a Dream Walker again, he'd like try to drag Cheyenne back from the edge he shoved him towards in the first place which could be really fun to play out.