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The Milwaukee Bucks may be somewhat stingy financially, but they've spent their draft picks like drunken sailors over the past several years. Forget about necessary blockbusters like the Jrue Holiday trade; the Bucks gave away four second-round picks for a few months of Nikola Mirotic. They gave the Cleveland Cavaliers a first-round pick in a trade that was at least partially a cap dump. Malcolm Brogdon-related complaints remain warranted, but the Bucks have spared no expense in terms of external additions. 

Well, the bill eventually comes due. The Bucks remain championship-less during the Giannis Antetokounmpo era, and they're running out of ways to improve enough to change that. Two of their starters are already in their 30s and a third, Khris Middleton, will get there in August. They are down to four tradable draft picks -- all in the second round -- and are pressed so dangerously up against the hard cap that making unbalanced trades from a salary perspective is virtually impossible. 

The degree of difficulty now is significantly higher than it was over the past few seasons. The Bucks no longer have free reign to give up whatever it takes to improve. They are going to have to get creative if they plan to upgrade ahead of the postseason. Here's everything you need to know as they try to do it. 

Needs

  • Individual shot-creation: Milwaukee's post-season struggles don't need to be rehashed. For all of his gifts, Giannis Antetokounmpo is not a championship-caliber, late-game shot-creator. The Bucks hope Jrue Holiday can be. They sought insurance against the chance that he isn't by pursuing Bogdan Bogdanovic in the offseason. They couldn't seal the deal. They'd still very much like to find another ball-handler to fill the role Bogdanovic couldn't. 
  • A small-ball center: The Bucks have spent the regular season experimenting stylistically on defense, and that has largely led to more switching. Brook Lopez can't switch. Certain opponents, especially Brooklyn, are going to force them to do so. The Bucks need a non-Lopez option up front to make that style viable. Giannis-at-center lineups have historically fared well for Milwaukee, but that would still create a need at forward. If the Bucks are going to pull this off, they need a bigger, switchable defender that can shoot. 
  • Bench production: Milwaukee's starters are world-beaters. Bobby Portis has been a revelation. Pat Connaughton is finally shooting consistently. After those seven players? The Bucks have no trustworthy reserves. D.J. Augustin has declined meaningfully. Bryn Forbes can't cut it on defense. Torrey Craig can't on offense. Thanasis Antetokounmpo's energy is infectious, but he provides little else. The Bucks need to at least find an eighth reliable player. Ideally, they'll enter the postseason with nine. 

Assets

  • Untouchables: Giannis Antetokounmpo, Jrue Holiday, Khris Middleton
  • Probably staying: Brook Lopez, Donte DiVincenzo, Thanasis Antetokounmpo
  • For the right price: Bobby Portis, Pat Connaughton
  • Let's make a deal: D.J. Augustin, D.J. Wilson, Bryn Forbes, Torrey Craig, Sam Merrill, Jordan Nwora
  • Tradable first-round picks: N/A
  • Tradable first-round swap rights: 2021, 2023
  • Tradable second-round picks: 2023-24 (own), 2025 (Indiana), 2027 (own)

Cap notes

  • The Bucks are currently above the luxury tax line. They can therefore only absorb 125 percent of their outgoing salary plus $100,000 in any trade, regardless of what tier of salary they bring in.
  • By virtue of using the non-taxpayer mid-level exception (on Augustin) and the bi-annual exception (on Portis), the Bucks are hard-capped at the apron ($138.928 million). They cannot exceed that amount for any reason. At present, they have roughly $500,000 beneath that line to spend.
  • The Bucks have only 14 players on their roster. If they make a trade that sends out more players than it brings in, they must have enough room beneath the hard cap to get back up to 14 through minimum-salary deals.

Expiring contracts

  • Jrue Holiday has a $27 million player option for next season. Assuming he opts out of it, the Bucks will have full Bird rights on him, and will therefore be able to offer him anything up to the max in order to retain him. 
  • Bobby Portis ($3.8 million) and Bryn Forbes ($2.5 million) both have player options for next season, but if either opts out, the Bucks would only have Non-Bird rights on them. They could only offer either 120 percent of their 2020-21 salary without dipping into their cap exceptions. 
  • D.J. Wilson will be a restricted free agent, and the Bucks will have full Bird rights on him. They can offer him anything up to the max in order to retain him, and have the right to match any offer sheet he signs with another team. 
  • Thanasis Antetokounmpo will be a restricted free agent, and the Bucks will have Early Bird rights on him. This subjects him to the Gilbert Arenas provision, which is explained further here. In all likelihood, though, it will not be invoked. If Antetokounmpo is signed to an NBA contract next season, it will likely be for the minimum. 
  • Torrey Craig will be an unrestricted free agent, and the Bucks will only have Non-Bird rights on him. They can only offer him 120 percent of his 2020-21 salary without touching their cap exceptions.  

Possible trade targets

  • Low-end -- Lou Williams: The Clippers have little reason to send Williams to the Bucks themselves, but if they wind up dealing him elsewhere, Milwaukee should consider weaseling its way into the deal with matching salary and some second-round picks. The Bucks don't have the assets to acquire many of the best bench shot-makers in the NBA, but Lou's age and status as likely salary ballast in any Clippers upgrades makes him somewhat uniquely available to Milwaukee. 
  • Medium-end -- P.J. Tucker: His decline as a shooter is concerning to most teams, but Brook Lopez has now shot below league average from behind the arc in back-to-back seasons, so the drop there would be minimal. Aside from Draymond Green, Tucker has been the poster boy for postseason downsizing over the past several years. He can handle center duties on defense against any Eastern Conference opponent aside from Philadelphia, and like Williams, is attainable for the Bucks given his age and contract situation. 
  • High-end -- Terrence Ross: Milwaukee wouldn't sacrifice DiVincenzo to get Ross, but could they entice Orlando with the improved Connaughton? The Magic know Augustin quite well and would probably be more amenable to taking on his contract than most teams. Ross will probably command a first-round pick if he is dealt, but if not, the Bucks might be able to jerry-rig a package based around their tradable second-rounders and a couple of players. 

Possible buyout targets

Guard -- Tony Snell: He isn't getting a buyout from Atlanta, but if he gets traded in a win-now move, it's not outside of the realm of possibility that Snell gives a bit of money up to hit the market with free agency looming. A return to Milwaukee would make sense for both parties, as Snell is a far more reliable 3-and-D option than anyone beyond Milwaukee's top seven. 

Forward -- Mike Scott: Another "if he gets traded to the right team" buyout candidate. Philadelphia actually uses Scott, and his salary will be necessary trade filler for it, but his shooting would make him an intriguing small-ball five for Milwaukee even though the 76ers have hardly actually used him that way. 

Center -- Robin Lopez: The Wizards would need to go back in the tank to free Lopez, but the Bucks had him a year ago and only lost him over financial constraints. They certainly wouldn't mind bringing him back for another shot at the title.