With Halloween now less than three weeks away, teams are slowly running out of time to negotiate new deals with their extension-eligible fourth-year players. Brandon Jennings is one player that could be extended by the end of the month, though a recent Marc Stein report suggested that's unlikely. Still, Bucks GM John Hammond told Ryan Ellerbusch of ESPNMilwaukee.com (Twitter link) that the team's chances of retaining Jennings long-term are "very good."
Even if Jennings and the Bucks don't work out an extension by the end of October, Milwaukee will still have the opportunity to re-sign the point guard next summer. Assuming the team issues Jennings a qualifying offer, he'll become a restricted free agent, meaning the Bucks will have the right to match any offer sheet he signs elsewhere. According to Ellerbusch, Hammond appeared confident the Bucks could match another team's offer, which shouldn't come as a surprise — if Monta Ellis opts out of his contract next July, the Bucks could be under the cap by $25MM+.
Recent reports have indicated that agent Bill Duffy figures to push for a maximum-salary deal for his client, which Chuck Myron of Hoops Rumors opined would be mutually beneficial for Jennings and the Bucks. Still, if Jennings is holding out for a max contract, the Bucks aren't under a ton of pressure to lock him up right away. The team would still have the opportunity to retain him at that price next summer, and could potentially even save a few bucks if the 23-year-old has health issues or a decline in production in 2012/13.