The Milwaukee Bucks had a dream regular season in 18-19. They finished with the best record in the NBA, and for most of the season had a historical scoring margin. Giannis Antetokounmpo became the NBA MVP, Khris Middleton made his first All-Star team, Mike Budenholzer won Coach of the Year, and Jon Horst won Executive of the Year. It was a major step forward for the Bucks, who had lingered around the fringes of the Eastern Conference playoffs for years.

Yet, the season left Milwaukee yearning for more. The Bucks fell to the Toronto Raptors in six games in the Eastern Conference Finals. The Bucks were an overtime defeat away from taking a commanding 3-0 series lead before losing four straight. 

Now, the Bucks are just starting to write this chapter of their history book. Antetokounmpo is signed for at least two more years and is eligible to sign a supermax in 2020. Eric Bledsoe, who is coming off a career-year, signed an extension that keeps him in Milwaukee through the 2023 season. And Budenholzer and Horst are entrenched as the combo to lead the team for the foreseeable future.

But for that future to be as bright as many hope, it’s important Horst keeps together as much of this roster as he can. Milwaukee has a tricky summer that could be full of the potential potholes that have derailed many a team on the road to contention. The Bucks have four contributors as free agents this summer and will likely be dancing around the luxury tax line when all is said and done. It’s up to Horst to keep it all in line and moving forward.

Let’s start with Khris Middleton. He went from being everyone’s favorite pick for most underrated player in the NBA to first-time All-Star. But he’ll be 28 before next season starts. Some have suggested he was only an All-Star in a watered-down Eastern Conference and that his previous years were actually better than last season. Despite all that, as a 6’8’’ versatile wing, Middleton will have plenty of suitors this summer. The Bucks may not want to go to a max contract to retain him but may have to. There are plenty of other teams who will offer a four-year max deal if Milwaukee won’t.

Another starter, Malcolm Brogdon really broke out this season. The former Rookie of the Year had a 50/40/90 shooting season, while putting up career-best numbers nearly across the board. He’s a restricted free agent, which allows the Bucks to match any offers he gets this summer. Because of Brogdon’s versatility to play either backcourt position, some team could extend him an offer that starts north of $20 million per season. That figure would force Milwaukee into an expensive decision.

Up front, Brook Lopez has fully embraced his career change from low post banger to three-point marksman. Lopez had this third consecutive season with over 100 made three-pointers, as he hit a career-high 187 triples. This is after making three total three-pointers over the first eight years of his career. The Bucks signed Lopez at the Bi-Annual Exception last year, after he was sort of the last man standing as cap space dried up around the league. Milwaukee will likely get no such bargain this year. If the Bucks won’t ante up for the stretch five, plenty of other teams will.

Re-signing Middleton and Brogdon is a simple matter of how deep into the luxury tax the Bucks are willing to go. Re-signing Lopez is about finding a workable solution to bring him back despite having only Non-Bird rights for him. That means Milwaukee has had to do some angling to create cap space to give Lopez a considerable bump over last year’s salary.

Horst started this process by shedding Tony Snell’s salary before the draft in exchange for Jon Leuer. Milwaukee saved about $3 million in the deal, but could also waive and stretch Leuer to come up with an additional $6 million or so in cap space for this summer. That’s money that could go a long way towards giving Lopez enough of a raise to keep him with the Bucks. Horst also sent away his first round pick in this past draft in the Snell/Leuer trade. This was part of the cost to get off Snell’s salary, but also cleared almost $2 million more in extra cap space for the Bucks as well.

The Bucks were unlikely to re-sign Nikola Mirotic either way, but he's already agreed to sign with Barcelona in what was a surprising pre-June 30th move.

Anytime a superstar plays for a small market team and they aren’t title contenders year in and year out, rumors abound that the superstar will eventually leave town. This has started to bubble a bit with Antetokounmpo despite his repeated desires to play nowhere but Milwaukee. The best way to keep him with the Bucks is to repeat last year’s success. And the best way to do that is to keep the band together as much as possible. It seems like Horst has put the team in position to do just that. If he can, the Bucks have a good chance to add an O’Brien Trophy to all the individual hardware they won last season.

Offseason Details

Guaranteed Contracts (7): Giannis Antetokounmpo, Eric Bledsoe, Bonzie Colson, Donte DiVincenzo, Ersan Ilyasova, Jon Leuer, D.J. Wilson

Partial/Non-Guaranteed Contracts (2): Sterling Brown, Pat Connaughton

Potential Free Agents (6): Malcolm Brogdon (RFA), Tim Frazier (UFA), Pau Gasol (UFA), Brook Lopez (UFA), Khris Middleton (UFA), Nikola Mirotic (UFA)

“Dead” Money on Cap ($4,872,604): Spencer Hawes, George Hill, Larry Sanders

First Round Draft Pick(s): None

Maximum Cap Space: $34.7 million

Projected Cap Space: $19.5 million