Five Key Offseason Questions: Milwaukee Bucks

The Bucks broke out in a big way in 2018/19, rebounding from a disappointing 2017/18 season to win an NBA-high 60 regular-season games and two playoff series before falling just short of the NBA Finals. A deep, talented roster put together by Executive of the Year Jon Horst was led expertly by Coach of the Year Mike Budenholzer and MVP Giannis Antetokounmpo.

The Bucks’ core players are young enough to build on this year’s results and improve upon them without major roster changes, but before that can happen, the team will need to address several contract situations. Of Milwaukee’s eight most-used players in the postseason, four are free agents and another is a strong candidate to be released due to an unwieldy contract.

Here are five key questions facing the franchise this summer:

1. Will Khris Middleton be re-signed?

The answer to this question appears to be a resounding yes. When ESPN’s Adrian Wojnarowski reported last week that Middleton would turn down his player option, he added that Middleton and the Bucks planned to work together on a new deal. Since then, Middleton’s name has barely popped up in the rumor mill, a hint that teams around the league view his return to Milwaukee as the most likely scenario.

So maybe the question shouldn’t be whether Middleton will be back, but whether his lucrative new contract (which could be worth up to as much as $189MM+ over five years) will be a worthwhile investment.

Despite earning his first All-Star nod in 2018/19, Middleton probably doesn’t qualify as a “star.” The 27-year-old is one of the league’s more reliable three-and-D options, but he has only cracked 20 PPG in a season once and was up and down in the playoffs this year. In the Bucks’ six-game series loss to the Raptors, Middleton struggled to slow Kawhi Leonard and averaged just 13.7 PPG.

Still, the Bucks have little choice but to commit big money to Middleton. Milwaukee isn’t a prime free agent destination, so it’s not as if the team can go out and recruit Klay Thompson to replace him. All of the Bucks’ moves this offseason will be made with an eye toward eventually securing a long-term commitment from Antetokounmpo, and allowing the team’s ostensible second-best player to walk in free agency wouldn’t be a good look.

Middleton’s new contract probably won’t be one of the NBA’s best values over the next several years, but the Bucks can’t afford not to offer it.

2. Will Malcolm Brogdon be re-signed?

While Middleton is the easiest pick as the Bucks’ second-best player, Eric Bledsoe made a case during the regular season, and Brogdon made his own case during the postseason.

After returning from a foot injury late in the second round, Brogdon was one of the Bucks’ only reliable offensive options against Toronto in the Eastern Finals, averaging 13.5 PPG, 5.2 RPG, and 3.3 APG on .443/.382/.667 shooting. He was also the team’s most effective defender on Leonard for much of the series.

Two-way guards like Brogdon, who shot .505/.426/.928 during the regular season, are popular on the open market, and there’s a chance he’ll command a big offer sheet as a restricted free agent. The Sixers, Pacers, Celtics, and Bulls are among the teams that have been cited as potential suitors, though Milwaukee will hope that those teams get scared off by Brogdon’s RFA status and go in different directions.

The Bucks, who have potential luxury-tax concerns depending on which free agents they bring back, reportedly have a “walk-away” number for Brogdon, but it’s not clear exactly how high they’re willing to go for him. An offer sheet exceeding $20MM+ per year isn’t out of the realm of possibility, and if it happens, it’ll be fascinating to see how Milwaukee responds.

The small-market Bucks likely don’t want to go into the tax, but they may have no choice if they want to retain their core and show Giannis they’re serious about contending.

3. Will Brook Lopez be re-signed?

One advantage the Bucks have when it comes to Middleton and Brogdon are their Bird rights, combined with their relatively small cap holds. Milwaukee will have to carry cap holds worth a combined $22.5MM to retain the Bird rights for those two players, and would be able to go over the cap later in free agency to give them big raises.

The team doesn’t have the same flexibility with Lopez, who is only eligible to receive a $4MM salary via his Non-Bird rights. If they want to re-sign him, the Bucks will need to use cap room or a mid-level exception.

Fortunately, those modest cap holds for Middleton and Brogdon give Milwaukee some options. If they retain those two cap holds and the non-guaranteed salaries of Pat Connaughton and Sterling Brown while waiving George Hill (who has a $1MM partial guarantee on his $19MM salary), the Bucks could create about $13MM in cap room. That’d be enough to make a strong offer to Lopez, who could theoretically sign for up to four years.

It looks to me like this is the Bucks’ Plan A. Using their cap room on Lopez, then going over the cap to lock up Middleton and Brogdon would allow the team to retain its three most important free agents, while losing Hill and Nikola Mirotic. Milwaukee would have the room exception (worth about $4.76MM) to make one more non-minimum signing in that scenario.

The only problem? If we assume a max salary for Middleton, and, say, a combined $32MM cap hit for Brogdon and Lopez, the Bucks would be over the projected $132MM tax line with three more roster spots still to fill.

4. Are there other ways for the Bucks to create additional spending flexibility?

In my view, the Bucks should be willing to go a little ways into the tax for this roster — the Raptors showed last season that paying that price for a talented squad can pay off in a big way. But I’m not the one paying the bills in Milwaukee.

Let’s say the Bucks would rather stay out of the tax, but still want to do all they can to re-sign Middleton, Brogdon, and Lopez. What options would they have?

The first would be to waive and stretch Jon Leuer. By acquiring him from Detroit in exchange for Tony Snell, the Bucks picked up a player on an expiring contract rather than one with two years left on his deal, which makes the idea of a waive-and-stretch far more palatable. Doing so would trim Leuer’s cap hit for 2019/20 from $9.5MM to about $3.2MM without too seriously impacting future seasons.

The other option for the Bucks would be to shop Ersan Ilyasova. The veteran stretch four has a solid season, but struggled to make much of an impact in the team’s most important playoff series vs. Toronto, and could lose some of his minutes next season to a more versatile two-way player like D.J. Wilson.

Ilyasova is earning $7MM annually and his 2020/21 salary is non-guaranteed, making it a fairly team-friendly contract for clubs in need of a floor-stretching big man. It’s not unreasonable to think the Bucks could find a taker for Ilyasova without needing to attach a significant asset.

Moving on from Leuer and Ilyasova could allow the Bucks to avoid the tax — or it could give them even more spending power under the cap if they’d rather try to turn those savings into another rotation player.

5. What outside reinforcements could the Bucks realistically add to their roster?

Even if the Bucks are able to re-sign Middleton, Brogdon, and Lopez in the scenario we’ve outlined above, they’d have holes to fill. Hill and Mirotic were solid contributors. Snell won’t return, and Leuer is unlikely to play a role in Milwaukee. If the club moves on from Ilyasova, his minutes would also need to be replaced.

In Connaughton, Brown, and Wilson, the Bucks have some young players who could be ready for larger roles. But a team with title aspirations would want to add a little more veteran help to solidify its rotation.

At the stretch four spot, it’s worth keeping an eye on former lottery pick Frank Kaminsky, who will reportedly become an unrestricted free agent. The Bucks have been linked to him in the past, and an underwhelming 2018/19 season in Charlotte may limit Kaminsky’s earning power on the open market, putting him in Milwaukee’s price range. JaMychal Green, Mike Scott, and Anthony Tolliver are among the other options that could intrigue the Bucks.

In the backcourt, Hill will be tough to replace. Even though he’s probably not worth his $19MM salary, his ability to handle the ball, make catch-and-shoot threes, and defend his position was valuable for the Bucks. It’ll be tough to find a player on the cheap who is quite that well-rounded.

Ish Smith and T.J. McConnell could be targets, but neither is a great shooter. I like the idea of Darren Collison or Seth Curry in Milwaukee, but they”ll receive plenty of interest and will likely get larger offers. We’ll have to wait to see what the Executive of the Year has up his sleeve to fill out the Bucks’ rotation.

Check out the Milwaukee Bucks’ offseason salary cap outlook right here.

Salary information from Basketball Insiders was used in the creation of this post. Photos courtesy of USA Today Sports Images.