However, that possibility got a lot murkier with the passing of Wednesday night's deadline to extend rookie contracts.
According to the Milwaukee Journal-Sentinel's Charles F. Gardner, the Bucks had no plans to extend Jennings' contract, which means he will be come a restricted free agent at the conclusion of the 2012-13 season.
And in holding off on extending his contract, Milwaukee gets the best of both worlds: It can keep the third-year guard if this ends up being the season he establishes some offensive consistency, or it can let him walk of the inconsistencies continue to plague him.
In the end, the risk of extending Jennings wouldn't have been worth it for Milwaukee. That isn't to say that Jennings isn't good, or that he doesn't have the potential to be. That's sort of the problem: He does have the potential, without a doubt. The question is whether or not he'll ever live up to that potential.
Count this as Jennings' final audition.
Last season, the Bucks were a team that was on the verge of making the postseason but couldn't quite get there, falling four games short of Philadelphia and finishing in ninth place in the Eastern Conference. If they're going to get where they want to get in 2012-13, Jennings figures to be one of the key players they will rely upon to make it happen.
Last season, he played the most minutes of his career—35.3 per game—and averaged 19.1 points, 5.5 assists, 3.4 rebounds and 1.6 assists. He shot about 42 percent from the field and 33 percent from three.
Objectively, his stat line looks pretty solid for a third-year player. But the Bucks' struggle with whether the former first-round draft pick can incorporate the kind of consistency into his game that he needs in order to justify the kind of contract extension he feels he deserves.
The Bucks also struggle with Jennings' commitment to the team. According to Pro Basketball Talk's Brett Pollakoff, Jennings has expressed an interest in playing for a "big-market team," and the Bucks certainly don't want to extend a player who isn't going to be content sticking around for the long term.
Maybe a really good season—a playoff season—is what it will take to compel Jennings to want to stay in Milwaukee. And if that happens in 2012-13, all the more reason to have some serious contract talks once the season ends.
Jennings seems like the type of young player you don't want to let get away. Considering how much Jennings would probably be expected to be paid if he signed an extension, though, the Bucks couldn't afford to take that risk without first getting more certainty that it would pay off.
If Jennings and the Bucks can get to the postseason, perhaps he will have proven himself worthy of a new contract. But if he and Milwaukee fall short again—and if the inconsistencies persist—it may be time to move on.