Will the bucks have the cap space to match if we make a max offer?
The Bucks have the ability to match, the question has always been do they think he's worth paying the Max. Giving Jennings something like 4/$52 would definitely be overpaying him considering what similar guys like Curry/Holiday/Lawson just resigned for. They were all in the low to mid $40s I believe.
Considering Davis and Anderson will probably outperform their contracts in the next 3 years you can afford to overpay a guy like Jennings. But that also means Demps needs to keep finding productive, cheap role players like Jason Smith, Ayon, Vasquez, etc.