The Milwaukee Bucks had much narrower goals to start the 2018-19 season. This was head coach Mike Budenholzer’s first season with the organization. Some of the team’s best talent was young. So maybe Giannis Antetokounmpo would develop a shot. And maybe Khris Middleton would take the highly coveted, vaguely defined Next Step. It would’ve been enough this season to just watch them check boxes on the greatness to-do list.
The Bucks outperformed from the start. They took that to-do list, crumpled it 29 feet from the basket, crossed over the entire city of Boston, yelled “WE WERE ACTUALLY ALREADY GREAT, JASON KIDD,” and drained the wad of paper. Budenholzer took many of the same Bucks players Kidd had (plus Brook Lopez) and made them move differently around Giannis. Suddenly the offense had spacing and took 3s often and shot them well. The defense utilized Giannis’s versatility and the roster’s length to earn the league’s best mark. Together, it made for the best net rating in the league. Milwaukee’s opponents found themselves squaring up with the future, a basketball-themed cowboys vs. aliens where the lead alien was actually a unicorn.
The Bucks quickly became the favorite to win the Eastern Conference. But just a few months removed from those measured preseason expectations, losing to the Toronto Raptors in six games of the East finals and not getting a chance at the defending champions feels disappointing. Something tells me the team of the future will bounce back from this. But what will it take this offseason to keep the Bucks intact?
Who is the top free-agency priority?
Re-signing Middleton is the most critical item on Milwaukee’s list this summer. With Antetokounmpo under contract until 2021 (and eligible for an extension in 2020), the second-most important piece on the Bucks is at risk of leaving. Middleton is expected to turn down his $13 million player option for next season and enter unrestricted free agency, coming off a season where he averaged 18.3 points, 6.0 rebounds, 4.3 assists, and 37.8 percent shooting from behind the arc.
“We’re gonna do everything we can to keep him,” one Bucks official told Yahoo in December. The urgency for the organization here can’t be overstated: Re-signing Middleton is a bigger priority for the Bucks than it would be for most other teams because they likely won’t have the open cap space to land a comparable talent on the open market given all of the other rotation spots they need to fill this offseason. And for players on Middleton’s level, Milwaukee isn’t a destination. So, like there are hometown discounts, there are hometown gratuities. It’s likely that the Bucks will have to offer Middleton a maximum contract, especially with so many teams holding money to burn this summer.
”Does he love Milwaukee enough to re-sign?” Bucks co-owner Marc Lasry asked ESPN rhetorically in February. “Yes. Enough to give us a real discount? No.”
Is it realistic to hold onto both Middleton and Malcolm Brogdon?
Milwaukee has more control over Brogdon, who will become a restricted free agent this summer. Missing eight weeks with a right foot injury is the last thing a player wants during a contract year, but Brogdon’s presence in the Eastern Conference finals (13.5 points on 44 percent shooting, 3.3 assists, 5.2 rebounds) made up for any missed attention.
Brogdon’s role is crucial. (Players who can shoot 50-40-90 don’t grow on trees.) If Middleton is the team’s second-in-command, Brogdon is its X factor. The Bucks’ Big 3 is clear—whether Giannis, Middleton, and Brogdon will ever be enough to win it all is not. The Bucks already extended Eric Bledsoe during the regular season; re-signing Brogdon and Middleton effectively locks Milwaukee into this core for the rest of Antetokounmpo’s contract.
Can the Bucks run it back?
The Bucks’ summer questions don’t end with two of their top three players. Lopez, signed for the veteran’s minimum last offseason, and Nikola Mirotic, a trade deadline pickup, will also hit free agency this summer. Mirtotic never fit in as well as the Bucks had hoped and was likely always intended to be a half-season rental; he is 28 and still a quality stretch-4 in a league desperate for frontcourt shooters, which will make him an appealing option for several teams this summer. Lopez, however, was an essential part of the Bucks’ success, a player whose ability to spread the floor unlocked Giannis on both ends. He may be 31, but he may also command a hefty pay raise, and the Bucks only hold his Non-Bird rights, and thus limited means of keeping him should they go over the cap.
Four players have non-guaranteed contracts next season, too: George Hill, Sterling Brown, Pat Connaughton, and Christian Wood. Hill’s $18 million salary in 2019-20 is second to only Antetokounmpo. However, if Milwaukee decided to waive Hill by July 2, Hill would receive only $1 million. (Thanks for the insurance, Vlade.) Yet, while waiving Hill seemed like a foregone conclusion when they acquired him in December, and may still be if the Bucks plan on staying out of the luxury tax, it would be a major blow to the backcourt, especially after Bledsoe’s uninspired postseason finish. The Bucks could also move Tony Snell or Ersan Ilyasova, who are guaranteed $11.6 and $7 million next season, respectively.
It’s funny that players other teams threw away are guys the Bucks needed this season and would like to have going forward, like Ilyasova, Hill, Bledsoe, and even Connaughton. Even the Bucks’ core of Giannis (the 15th overall pick in 2013), Middleton (the 39th overall pick in 2012), and Brogdon (the 36th overall pick in 2016) was mined without a single lottery pick. Will the organization will be willing to pay the price to hold onto some of their best finds, or will it try to move on and find the next versions of them? Either way, the front office will be forced to act somehow to ensure the team of tomorrow still has a bright future.