Now going into his fourth season, the 22-year-old has one last opportunity to prove he deserves a max-contract this summer when he'll become a restricted free agent. You can't complain about what he's done so far, averaging nearly 17 points for his career, including 19.1 last season.
Jennings isn't known as much of a distributor, but he'll still pick up over five assists a game. His poor assist ratio ("the percentage of a player's possessions that ends in an assist") was 53rd among point guards, but still good enough to keep him ahead of Russell Westbrook.
It says more about how frequently Jennings is used (ninth among point guards) and how he's used. The 6'1" guard scored more points last season than Tony Parker, Ty Lawson, Tyreke Evans, John Wall, Lou Williams, Jrue Holiday, Mike Conley and Steve Nash.
A number of those point guards have a higher profile than Jennings, but the only ones to actually score more points per game were Russell Westbrook, Deron Williams and Chris Paul.
Though his efficiency leaves something to be desired on face, his adjusted field-goal percentage (which weighs three-point makes more heavily) shows that he is scoring more points per field-goal attempt than Williams, and almost as many as Westbrook.
In other words, you want the guy shooting the ball.
The question is how much you want to pay him to do so.
The up-and-coming star was non-committal about his free agency in February and was reportedly frustrated with how things were going in Milwaukee. Golden State acquired combo-guard Monta Ellis a month later, and it's not yet clear how that'll impact Jennings' thinking.
You can be pretty sure it will impact the Bucks' thinking though, now that they have a scoring guard who can create his own offense and pass the ball just about as well as Jennings can. If the point guard scuffles this season or the organization deems him too expensive, they'll still have Ellis—and plenty of cap space with Beno Udrih, Samuel Dalembert and Mike Dunleavy all coming off the books.
If Milwaukee trades or amnesties Drew Gooden next summer, it could have another $7 million to work with.
So GM John Hammond will have some decisions to make, especially if Jennings has anything short of another All-Star caliber campaign. If the team thinks it can do better on the open market, it very well may let Jennings walk to the highest bidder.
But that's assuming there's something better on that open market and that he's willing to come to Milwaukee.
Or, it's assuming that Jennings won't remain a happy camper for long, in which case it might make more sense to trade him this season or in a sign-and-trade deal next summer.
There are certainly scenarios in which Jennings doesn't remain a Buck. Either way, he'll have every incentive to maximize his value with what will likely be his third breakout season. Breaking out enough for an invitation to his first All-Star game certainly wouldn't hurt his cause.
Don't be surprised if Jennings' defense is a little extra lively this season.
He also might want to work on his ability to finish around the basket, something fellow third-year point guard Ty Lawson has mastered more quickly despite being a couple inches shorter.
But while there's work to be done for Jennings, there's no shortage of talent to build upon. There will be more than a few teams watching him do just that this season, wondering what he'd look like in their uniforms.
If I were the Bucks, I wouldn't let them find out.