The thing with Jennings is he has greatness in him. I think everyone knows he has a chance to be special. He just turned 23 years old, and as has been said, he really hasn't played with a lot of help around him. The guy for all of his imperfections was 11th in PER last season amongst PG's. As we have seen this year, through three games he has averaged 17.7 points, 10.3 assists, and 4 steals a game. 4th in PER behind only Kyle Lowery, Kyrie Irving and Chris Paul.
It would be a bold move, there would be risks, but I think the possible reward would be well worth it. You have to dream big.