Market is set

For those of you who are interested in the long term future of the Bucks, and I'm talking to both of you, there was a signing today that Buck's fans should notice. Ty Lawson signed his 4 year extension for 48 million today with the Nuggets. Lawson was one of the members of the 2009 draft also known as the point guard draft, because 5 of the top 10, and 10 of the top 21 players drafted were point guards, including the Buck's Brandon Jennings at #10. This signing is significant because while Lawson was the 7th point guard drafted that year, his numbers compare favorably with the best PGs in that draft. It can be debated how good Jennings is, and how much he deserves, but I think it is reasonable that his next contract should be in the same ballpark as Lawson.
Jennings had expressed interest in exploring his options in free agency earlier in his career, which was no surprise given his big city roots, and the Bucks likely role as 2nd class organization. It was somewhat surprising when Jennings recently discussed publicly that he wanted to get an extension done before the 10/31/12 deadline for 2009 rookies. Milwaukee has a lame duck coach and GM, and their 2 biggest stars in Jennings and Ellis can be free agents after this year, so my guess is they will wait on signing Jennings. Jennings will be a restricted free agent so the Bucks can always match any deal he gets.
The danger in waiting is that Jennings has a great year, that also turns out to be a career year in 2012-13.  Some other team desperate for talent offers him a max deal which the Bucks then have to match or lose their only marketable star. The Bucks then end up with a Mike Redd situation where they have a very good player who just isn't worth a max deal, but whose contract is restrictive enough they can't bring in any other major talent. They then find themselves back in salary cap hell.
Here's hoping Jennings signs a reasonable contract extension before tomorrow's deadline.