The Milwaukee Bucks will always have 2021.
No one can ever take that away from the franchise. No one can ever take that away from Giannis Antetokounmpo. The latter now appears to be pulling away from the former but it is that championship ride in 2021 that kept the flame burning even this long.
As Antetokounmpo dared himself to dream and be the best player he could possibly be, he dared the same of the Bucks and they ascended to greater heights as well. It’s the reason why Milwaukee was able to win its first championship since 1971 and it is now the same reason the two sides are drifting apart.
The Bucks want to keep Antetokounmpo. Turning 31 on Saturday, Antetokounmpo wants to win another championship. As much as Milwaukee would like to once again align and aspire to the same heights as one of the most dominant players in league history, the reality is it can’t.
What’s got the Bucks stuck between a rock and a hard place and facing the possibility of trading Antetokounmpo? Let’s take a deeper look at the decisions — good and bad — that have brought us to this point.
DiVincenzo Trade Was Step In Wrong Direction (Feb. 2022)
Bucks trade: Donte DiVincenzo, Rodney Hood, Semi Ojeleye
Bucks receive: Serge Ibaka, two second-round picks, cash considerations
Donte DiVincenzo was an important member of the Bucks’ championship season, even if he missed the majority of the team’s postseason run. He played 66 regular-season games and averaged the fourth-most minutes on the team, putting up 10.4 points, 5.8 rebounds, 3.1 assists and 1.1 steals in his trademark rugged and determined style.
Perhaps, Milwaukee believed that, in winning the title despite DiVincenzo missing all but the first three games of the playoffs, it could manage just fine without him. It’s rumored the Bucks didn’t want to be the ones to pay his next contract and this move at the Feb. 2022 trade deadline sealed that.
With the Bucks having most of their salary cap devoted to Antetokounmpo, Jrue Holiday, Khris Middleton and Brook Lopez, how they managed the margins was going to be a critical piece of contending again. Dealing DiVincenzo for a player in Ibaka who was well past making noteworthy contributions was a signal the Bucks were losing their way.
Some will argue the tax situation dictated he be moved but you’re not supposed to be playing tax-ball if you’re in contention mode. The move looks worse when remembering Milwaukee fumbled the bag in 2020 with a sign-and-trade that would have returned Bogdan Bogdanovic for DiVincenzo.
Holiday Trade Marked Beginning Of The End (Oct. 2023)
Bucks trade: Jrue Holiday, Grayson Allen, 2028 first-round pick swap, 2029 first-round pick, 2030 first-round pick swap
Bucks receive: Damian Lillard
Jimmy Butler and the Miami Heat showed no fear of the deer in eliminating the Bucks in the first round of the 2023 playoffs.
Antetokounmpo got injured during the series and that spelled doom as Butler took over one fourth quarter after another. Still, the series loss stung and was viewed as a step back from losing in seven to the Boston Celtics in the conference semis the year before.
Milwaukee and Antetokounmpo may have felt there should have been enough in place to withstand an Antetokounmpo injury in the first round, so the move for Damian Lillard was made. As it turned out, Lillard wasn’t the answer either.
Additionally, Grayson Allen was a solid role player for the Bucks and he was lost in the trade as well. Milwaukee did not get what it hoped to from pairing Lillard and Antetokounmpo together and lost a chunk of future depth in the form of the draft capital surrendered.
In hindsight, the Bucks may have traded the wrong player. Middleton’s ankles were already a cause for concern and time was running out on redeeming decent value for him. This isn’t to say Middleton could have netted Lillard but rather a different trade route may have been ideal. Holiday still had some good seasons left, as he showcased in helping the Boston Celtics to the 2024 title.
Middleton Trade Reeked Of Desperation (Feb. 2025)
Bucks trade: Khris Middleton, AJ Johnson, Delon Wright, 2028 first-round pick swap, cash
Bucks receive: Kyle Kuzma, Jericho Sims, 2025 second-round pick
It was clear the Bucks were heading toward the 2024 postseason with no real shot at contention. Winning a short, tournament-style NBA Cup is one thing, taking home the Larry O’Brien trophy again was going to require a much higher level of sustained excellence. That wasn’t going to be possible with where Middleton was health-wise during the 2024-25 season.
Despite having procedures done on both ankles in the offseason, Middleton could never quite get right. In an effort to recoup someone who could be a contributor in the playoffs, the Bucks could only come up with Kyle Kuzma and Jericho Sims while also surrendering former first-round selection AJ Johnson.
This is a case of having waited too long to move on from Middleton and paying the price. He never had the type of value that was going to bring back a star but there was a period between 2021 and 2023 he would have netted someone quite a bit better than Kuzma.
It may have also been prudent to find value for Brook Lopez while they could before he left in free agency this past summer.
Waiving, Stretching Lillard Was Death Knell (July 2025)
Bucks use the waive-and-stretch provision on Damian Lillard, with $22.5 million of dead money on the books each year through 2030. Bucks use the flexibility acquired through that move to sign free agent Myles Turner to a four-year, $109 million contract.
It’s hard to even call this a Hail Mary. The writing was on the wall once Lillard ruptured his Achilles last postseason. In one way, it’s admirable general manager Jon Horst did everything in his power to maneuver and build a bit of a different roster.
The reality, with the power of hindsight, is coming up with the short end of the stick on the Holiday and Middleton deals while Lopez declined and departed in free agency left this team with an insurmountable task in order to contend for a championship.
Here we are now, with the Bucks 10-13 and 10th in the Eastern Conference. Antetokounmpo has a right calf strain and will reportedly miss two to four weeks, which means they could very likely be out of the playoff picture by the time he returns.
Missed Opportunities In The Draft
2022: Selected MarJon Beauchamp 24th overall
Some of the players the Bucks missed out on in the vicinity of this pick include Nikola Jovic, Peyton Watson and Andrew Nembhard. As mentioned previously, considering the franchise’s lack of flexibility, the moves around the margins are critical and nailing late first-round picks can sometimes be pivotal.
What the Bucks would give for any of the players above, especially Nembhard and Watson.
2024: Selected AJ Johnson 23rd overall and Tyler Smith 33rd overall
Johnson was traded as part of the Middleton deal but that should have been a tougher negotiation. Kyshawn George was selected with the very next pick, Terrence Shannon Jr. went 27th and Ryan Dunn was picked 28th. While Tyler Smith was the choice at 33, Ajay Mitchell went 38th and Jaylen Wells went 39th. Smith isn’t even on the roster anymore either.
All the pieces matter. The less Milwaukee had to work with, the more it needed to stretch every dollar — and not in the sense of the Lillard move.
No Real Future To Build Toward
Cash strapped and draft strapped is a horrible place to be but the Bucks find themselves there. Milwaukee’s pick in 2026 is possibly its best opportunity for the next little while as it will be either their own pick or New Orleans’. The Pelicans will also receive the more favorable 2027 first-round pick courtesy of the Holiday trade years ago. And the Bucks gave up swap rights for their 2028 pick.
Milwaukee won’t have a first-round pick in 2029 and the 2030 pick has Portland owning swap rights. The Bucks have no second-round picks for the next five years — unless the Utah Jazz somehow pick between 56th and 60th in the upcoming Draft.
The Bucks did a lot but also missed out on some meaningful opportunities. They will argue they did the best they could with the information available at the time. It’s all moot as Antetokounmpo is focused on what he has in front of him right now.
Antetokounmpo will have a lot of time to think as he sits out with the calf strain. It will also give the Bucks plenty of time to sink further down the standings and likely push their superstar to make the one request they’ve tried everything they could to avoid.
Things didn’t work out the way they’d hoped after 2021 but they’ll always know they did what they could.
