I like Greg and never wanted him to enter the portal. That said, if you are the staff, can you ever really trust a kid who entered portal and decided to come back? How do you know he won't change his mind again in August? If my job depended on winning games, I would be tempted to take another kid if he wanted in, even if he wasn't a huge upgrade over GW.
By all accounts, Greg is a good kid with a good family. If he had a sit down with CMA and assured CMA he was staying, I assume that would be good enough. In today’s climate, there are no guarantees with any player.