But is there any way to give him a PillowBear?
Sure:
[spoiler]just use Reyes/Ray to take the PillowBear from the hotel room of Boris and give it to Ransome.
[/spoiler]
Thank you missed that. I think due to first time I played the PillowBear was pruned from my inventory due to completing a chapter before I thought about giving it to him.
Hmm, he don’t seem to care. I guess that was not the toy he was looking for. Should have known. 
I somehow assumed that the contact Franklin was on the phone with was Ransome, and the result of Ransomes toy idea was the PillowBear.
No, it’s actually a prototype Ransome the Insult Clown come-back doll.