With that reality looming comes an important decision for both Jennings and the Bucks organization. For the Bucks, the question is whether Jennings is a player whom the franchise can build around, while Brandon Jennings must decide whether Milwaukee is the best place for him.
To best predict what is going to happen this offseason, its important to look at it from both sides. Is Jennings worth as much money as he will likely command in this crazy NBA market? Also, will Brandon find another place where he can score a large salary while maintaining his ball-dominating role?
Over his first three seasons, Brandon Jennings showed improvement in his offensive game. In each season, his shooting percentage went up, reaching 41.8 percent last season after seasons of 37.1 percent (as a rookie) and 39 percent in his second year. With that, his scoring numbers also went up from 15.5 to 16.2 to 19.1 points per game.
Other than scoring, however, Jennings failed to raise his statistics in any meaningful way. His assists per game were about the same as his rookie numbers, although last year he began playing alongside Monta Ellis, who averaged six assists per game.
Brandon also stabilized at 3.4 rebounds per game, which is solid for a 6'1" guard. Finally, Jennings had slowly raised his steals per game from 1.3 to 1.6 per game, again not a noticeable difference.
This season, however, Brandon Jennings has raised his game to a whole new level. He is averaging 17 points per game on 46.7 percent shooting while adding 13 assists and a whopping four steals per contest.
Those numbers point towards a more efficient, better distributing point guard, who should be quickly locked up with a contract. If Jennings is able to continue playing like he has so far, the Bucks decision to offer him a max contract should be easy.
If, however, Jennings digresses and continues to shoot 17 times a game at under 42 percent, then Milwaukee should refrain from offering a five-year deal and see what the market offers him. If he is offered anything more than the four years and 44 million dollars that Stephen Curry received, then the Bucks should think twice about signing him.
For Brandon Jennings, the decision of whether or not to stay with the Milwaukee Bucks comes down to three factors.
The first is winning, plain and simple. Does Brandon Jennings believe he can win enough games with the Bucks? The answer for that should be yes.
Already this season, the Bucks have taken down Boston and Cleveland, with impressive showings in each. They have been able to put up points and have both promising young players as well as solid veterans like Monta Ellis. Milwaukee certainly won't be competing for a championship this season, but they have a few nice pieces and should continue to improve in the coming seasons.
Will Brandon Jennings Re-sign with Milwaukee?
The second factor goes along with the ability of his team to win games: whether Jennings can find a winning team that will allow him to play his style.
Are there any teams out there that are already in a position to win and would allow Jennings to come in and dominate the ball while shooting 15-17 times per game? The quick answer to that would be no.
While Jennings certainly wants to win, he is still young and is probably just as hungry to develop his own game and statistics. He is not yet at the point where winning a championship is the all-consuming motivation, as it may later in his career.
Finally, where Jennings ends up may come down to money. The Milwaukee Bucks can offer him an extra year along with more money than any other team.
More than that, however, Brandon may find that he is not worth a max contract and will likely be offered a deal for slightly less money. If that becomes the case, any offer less than the max will probably be matched by Milwaukee.
If Jennings continues to play how he has so far this season, he may warrant a max contract and the Bucks would likely offer him a five-year deal, something that would be difficult to turn down.
Brandon Jennings is almost certainly going to end up in Milwaukee next season. The Bucks offer him complete control of the team, as they have no other serious options, and can offer him more money.
If Jennings is able to warrant a max contract, then he will be offered extra money by Milwaukee which would be hard to reject.
If, on the other hand, he is given a contract similar to Stephen Curry, then the Bucks will still likely match the offer. The Bucks simply do not have enough assets to let Brandon Jennings go through free agency. If he leaves, it will probably be through a trade before this season's trade deadline.
Jennings will continue to be a polarizing figure in Milwaukee for years to come.