Jennings' days with the Bucks might be coming to an end.
As the final buzzer sounded on the 2012-13 season for the Milwaukee Bucks on Sunday, the team thought process immediately shifted from winning a playoff series to executing the perfect offseason plan.
But what is the perfect plan?
Through free agency, the Bucks must make crucial decisions on who to bring back and who to potentially sign. In the draft, they need to make smart picks that will solidify the roster for the future. Lastly, they need to decide on a new coach after recently parting ways (h/t Charles Gardner of the Milwaukee Journal Sentinel) with Jim Boylan.
Potentially Losing an Entire Backcourt
Heading into the summer, making decisions on the future of Monta Ellis, Brandon Jennings and J.J. Redick is of utmost importance.
Conceivably, the Bucks could lose all three to the free-agent market.
And that might not be the worst thing.
After limping to a 38-44 regular-season finish and getting swept out of the playoffs by the Miami Heat, things aren't exactly heading in the right direction.
Ellis is scheduled to make $11 million next season but has an early-termination option on that deal.
Recently, Gery Woelfel of the Journal Times reported that Ellis would more than likely exercise that option and become a free agent.
On the other hand, Jennings has a qualifying offer of $4.3 million from the team for next year.
While he'll almost certainly be offered more than that elsewhere, the real question is whether or not the Bucks will match whatever that offer might be.
There was no love lost between Boylan and Jennings, so perhaps this is Milwaukee's way of saying it's committed to its starting point guard.
Which of the three should the Bucks focus most on retaining?
Finally there's Redick, an unrestricted free agent that has a lot of thinking to do prior to signing a new deal.
He must determine whether he wants to play for a contender—which likely means less money—or potentially get more money and more playing time for a team like the Bucks.
And though the possibility of all three leaving is there, the firing of Boylan might be an indication that they're going to do everything within reason to re-sign Jennings.
Don't be surprised, though, if Jennings or Redick—and possibly both—are back next season.
Potential Offseason Signings
The 2013 free-agent pool isn't full of big-name talent, but there are some names that the Bucks should take a serious look at.
Assuming Jennings gets better offers elsewhere, letting him walk and pursuing Jeff Teague may possibly be the wisest move the franchise could make.
Continuing to improve, Teague posted career highs with 14.6 points and 7.2 assists per game while shooting a respectable 45.1 percent from the field.
Unlike Jennings, Teague is a more efficient scorer and has a pass-first mentality. This allows for a smooth flowing offense that functions in an efficient manner—Atlanta was seventh in field-goal percentage.
Outside of Teague, the Bucks should look at potentially signing Andre Iguodala.
If Jennings, Ellis and Redick were gone, though, they could easily afford to pay him.
Iguodala averaged 13.4 points, 5.6 assists and 5.5 rebounds per game this year while playing great defense—something the Bucks desperately need.
And in a more featured role, he could easily find himself scoring around his 2007-08 career-high of 18.1 points per game.
If the Bucks were to continue looking for defense, Tony Allen of the Memphis Grizzlies is an unrestricted free agent.
Allen doesn't provide a ton of offense, but his value defensively is no joke, as evidenced by his 4.1 defensive win shares this season.
If they really wanted to make a splash, the Bucks could make a run the Hawks' Josh Smith.
According to ESPN's Chad Ford, the two teams were apparently very close to agreeing on a deal that would have sent Smith to the Bucks at the deadline:
Hearing Hawks pulled out of 3 way deal with Bucks & Magic that would've sent Josh Smith to Milwaukee at 2:59 p.m.— Chad Ford (@chadfordinsider) February 21, 2013
With the interest they've already shown, it's not unreasonable to believe they might continue to show it.
Ultimately, the Bucks must decide whether to go through a rebuilding phase or attempt to compete again next season. Once that choice is made, they should have a clearer picture of who to target on the market.
Depending what happens with the backcourt situation, the Bucks could go in several directions when draft day finally arrives in June.
Currently, DraftExpress, NBADraft.net and HoopsWorld each have them selecting a different player with the 15th pick.
DraftExpress has them taking Gorgui Dieng out of Louisville.
Dieng would provide the Bucks with another excellent defensive piece in the paint, but it's a pick that doesn't quite make sense with Larry Sanders and John Henson already on the roster.
NBADraft.net has them taking Giannis Adetokoubo, a 6'9" small forward from Greece, in that same spot.
With Ersan Ilysova capable of playing the three if needed and Luc Mbah a Moute still under contract, this pick wouldn't make a ton of sense for Milwaukee either.
Finally, HoopsWorld has the Bucks taking Russia's Sergey Karasev at No. 15.
Unlike the first two, this wouldn't be a bad pick.
At 6'7", Karasev would be able to slide down to the 2 if necessary, and he's a threat offensively. In the 2012-13 Eurocup, he averaged 16.1 points per game on 44.2 percent shooting from the field and 49 percent shooting from three-point range.
Clearly, he'd be a good addition if the Bucks need scoring.
If Jennings, Ellis and Redick—or any two of the three—are no longer with the team by draft night, they should look at backcourt help.
Some names that would likely still be around when it came time to pick that would be of value to the Bucks are Tim Hardaway Jr., Dennis Schroeder or Lorenzo Brown.
As for the second round, they could add a small forward like Andre Roberson or Rodney Williams if they're not intent on re-signing Mike Dunleavy.
Much like everything else, a lot of what happens during the draft depends on what happens with Jennings, Ellis and Redick.
Hiring a New Head Coach
While deciding the future of the roster is important, hiring the right head coach is of equal significance.
With Boylan out, Milwaukee's coaching search begins.
Both men are familiar with coaching roles in the state of Wisconsin.
Van Gundy served as head coach for the Wisconsin Badgers during the 1995 season after filling the assistant role for the prior two.
Meanwhile, Sampson spent two years as an assistant coach with the Bucks under Scott Skiles, meaning he likely has some familiarity with the franchise.
Van Gundy—who arguably got the shaft in Orlando—is the clear front-runner due to a resume that includes a trip to the NBA Finals in 2009 and coaching two All-Star teams.
With a group of players that buy into his system, Van Gundy could have success in Milwaukee, much like he did in Orlando.
If the team was looking to hire a fresh face, Sampson wouldn't be a bad choice.
His coaching record in the college ranks speaks for itself, and he went 7-6 filling in for Rockets head coach Kevin McHale when he left the team due to his daughter's tragic death earlier this season (h/t USA Today).
Other names that should be considered are Indiana Pacers associate head coach Brian Shaw and Patrick Ewing.
Both men have long stints as assistants and deserve a shot at coaching their own team.
Whichever choice the Bucks make, they must be patient and give the new coach the adequate time it takes to implement changes.
It's going to be an interesting offseason for Milwaukee, but following this plan should make for a smoother transition if the roster looks much different from this season.