We’ve discussed the difficult matter of extending Brandon Jennings’ contract before.

Jennings will be a restricted free agent at the end of this season. (Photo by David Liam Kyle/NBAE via Getty Images)

The deadline is October 31 by 5 PM. That’s tomorrow for those without a calender. So we won’t have to talk about it much longer. At least we won’t have to bring it up again for a few months, but we’ll definitely need to discuss the matter further, as it doesn’t sound like Jennings is going to get an extension.

The Bucks and Jennings are not going to reach an extension deal. One source close to the process said Jennings’ camp was looking for a deal in the $9 to $10 million range and the Bucks just don’t seem willing to engage that at this point. For Jennings to have a shot at a deal in that range, he’ll have to earn it on the court this year or get another team to offer it as a restricted free agent next summer.

On the local front, Gery Woelfel is equally pessimistic.

If this $9-10 million thing is serious – and who knows where that information came from – it’s a surprise that the Bucks wouldn’t be more engaged in talks. But this is as crucial a season as I can remember for the Bucks. The general manager and coach are both in the last year of their respective deals. The star player is entering restricted free agency. The second best player (well, in my mind third, but he’s often mentioned before Ersan Ilyasova), Monta Ellis, can opt out after the season. The team has missed the playoffs and finished in the dreaded ninth position in each of the last two seasons.

This is the season that will decide the Bucks future.

Perhaps Senator Herb Kohl doesn’t want to commit to a player that hasn’t shown he alone can get the team to the playoffs, regardless of what the cost is. In terms of simple market rate, $9-10 million sounds about right for Jennings. But could the Bucks look to blow it all up and start over if this season doesn’t go according to plan? Not resigning Jennings could be an indication of that sort of thinking. Keeping Jennings and Ilyasova and some of the younger players is just the sort of thing that could keep the Bucks mediocre past this season.

At any rate, it looks like Jennings will be able to test the market and bring back a deal to the Bucks after the season. Milwaukee still holds leverage of course, as they can match any deal he gets. But if Jennings has a big, breakout season, the Bucks could be kicking themselves for not locking him up now.