While his 2009 draft mates Ty Lawson and Stephen Curry have finished signing their contract extensions in the offseason, Brandon Jennings and his party are still undecided.
The fact that the Bucks and Jennings did not come to an agreement shows that either the organization is still unsure of Jennings as the future franchise centerpiece, or that Jennings hasn't shown enough interest in staying in Milwaukee.
It has been reported a month ago that Jennings is willing to weigh his options in the offseason and suggested that he might want to play for a big-market team, as opposed to the Bucks (via Chris Broussard of ESPN).
Although Jennings' numbers have been relatively steady this year, he's shown improvement in his decision-making and passing since he came into the league. By not trying to sign him to an extension would hurt the Bucks in the long-term, since they will probably be forced to match a much bigger contract that another team is definitely going to offer him.
He's only 23 years old and is already a borderline All-Star, so it won't be a surprise if some team out there coughs up a hefty chunk of money for him. A small-market team like the Bucks will certainly have trouble deciding whether or not to put their fortune into Jennings.