John Hammond signed an extension to be the Bucks general manager through the 2015-2016 season, 3 full seasons from now. His newly hired coach Larry Drew just signed a contract for 3 years with a team option for a 4th. The Bucks just signed OJ Mayo to a 3-year 24-million-dollar contract, and Zaza Pachulia to a 3-year 16-million-dollar contract. Ersan Ilyasova signed a 5-year contract last season, but only the first 4 years and $32 million are guaranteed meaning it will effectively expire after 3 more years assuming he doesn't vastly outperform his deal and earn the 5th year. That leaves the Bucks with about 23 million in expiring contracts after the 2015-16 season. The Bucks are high on last year's rookie John Henson and his rookie deal will expire after the 2015-16 season. If he turns out to be the player they are hoping he becomes then he will certainly eat up some of that salary cap space on his 2nd contract.
Through Hammond's tenure the Bucks have done a pretty good job dumping bad contracts and the have just one currently in Drew Gooden's 5-year 32-million-dollar deal. That deal was inked in 2010 and has just 2 years remaining. The only other veteran contract on the books is a reasonable deal with Mbah-a-Moute for 4 years and $19 million which is 2 years in. Both Mbah-a-Moute and Gooden come off the books the season before Hammond's contract expires.
Udoh, Ish Smith, and Sanders will all be free agents after this season, but only Sanders is expected to stick around after this year. His value is difficult to figure. He has developed into a good player but is far from an all-star talent. The Bucks will have the right to match any offer as he will be a restricted free agent so the market will figure out what he is worth after another full season as a starter.
There are no players currently under contract past the current John Hammond contract, which bring us to the two players who will soon. Giannis Antetokounmpo was just drafted by the Bucks, but will likely not play any significant minutes for at least 2 seasons. The question is when do the Bucks sign him. Hammonds said after the draft that they intended to sign him right away and bring him in to practice/play with the Bucks, or more likely in the D league. That would start the clock ticking immediately on his 4-year rookie contract. If he stays overseas for a year or two then he would still be on his rookie deal whenever he came to the Bucks. There is a pretty high likelihood that he is a bust, as most 15th picks are. His future will not likely determine Hammond's future unless he turns into a star, in which case Hammond looks like a genius and won't have to worry about his next contract. What about the other soon-to-be Buck, Brandon Jennings.
There is no doubt the Bucks will sign Jennings, whether it is by negotiation, or by using their matching rights on another teams offer since he is a restricted free agent. He is the only marketable player on a bad team and the Bucks gain nothing by letting him walk. Kohl will not allow his only money making player to walk out the door for a few extra million dollars. That doesn't mean they will keep him for the length of the contract, as he will be trade bait the instant he signs. The only question is do the Bucks really believe in him enough to use their Bird rights on him and give him a 5-year deal, or will they just give him/match on a 4-year deal to limit their long-term exposure. My guess is the later.
So where does the 3-year plan take the Bucks? In the short term, probably to the cellar of the central division. The Bucks won only 38 games last year, and they replaced Monta Ellis with OJ Mayo so it's hard to see how this team will be better. Next season looks like a lottery season, but next year is about sorting out the young guys more than winning anything. Jennings and Mayo will hog the ball and the shots, and hopefully not destroy their trade value in the process. The question the Bucks need to figure out is if Henson and Sanders are good enough to be the staring bigs on a playoff team, or if they are just more journeymen assets the Bucks will use to make future trades.
After this season, the Bucks should have a lottery pick in a strong draft. That pick will probably be the deciding factor in Hammond's future. Hammond will have to decide about Sanders next season, and he will hopefully have enough information to decide what Henson will be. If Sanders, Henson and Giannis all pan out, and the 2014 pick is a hit, then the Bucks could return to the playoffs by the end of the 3 year plan. That seems like a lot to ask, but it's probably all Bucks fans can hope for right now.
A new stadium and an ownership change to a stable local ownership group is unfortunately about as likely, but far more important to the Bucks' future.