I'd almost rather have a strong 3rd big or role player than Jennings who we know we're not winning with and who they're not trading anyway.
I suppose the flip side is to flip him next year.
Jennings has always been on a bad team, and has always been on extremely offensively limited teams. Give him some talent who can also score, and maybe he would become less selfish. I think it's a risk that can be made with little consequence. It doesn't work out, don't re-sign him.