Milwaukee Bucks Outlook – Post Damian Lillard Era

gregory spicer – 07/18/2025 – nba offseason

The Bucks nearly broke the internet this summer when they decided to waive Damian Lillard and give him the biggest “stretched” contract of all time. Lillard had two years and $112 million remaining on his deal. The Bucks waived him and adjusted their payments to take place over five years. Now, instead of two massive 60-million-dollar years, the Bucks will pay Lillard $20 (ish) million for the next five. 

Constructing a waiver of this quantity comes with countless pros and cons, but we are going to try and break down what position this puts Milwaukee in. 

The Cons

The bottom line of this deal is that the Bucks are now stuck paying a lot of money to someone who won’t touch the court for their team. No organization has ever won a championship with over $20 million in dead money, but with superstar Giannis Antetokounmpo potentially wanting out, the expectation will be to compete. 

(Chart details the percent of cap space LILLARDS’ dead money will take up each season)

Building a contending team will likely require some magic from either the draft or the owners. The draft could allow them to find young players that develop into inexpensive, all-star caliber talent. The ownership could give the front office flexibility to get deep into the luxury tax, but even if they are given the green light to spend big, going into the luxury tax/aprons comes with restrictions. 

  • Loss of trade/signing exceptions
  • Extra tax payments from owners
  • Limitation of draft picks/flexibility

The loss of Lillard isn’t just due to the waive, though. On April. 27, Lillard tore his achilles, putting him out for the entire upcoming season. This leaves the Bucks’ backcourt in a very difficult position. With no chance of a rebuild as long as Antetokounmpo is on the roster, Milwaukee is hoping that their affordable wildcards (Gary Harris, Gary Trent Jr, Kevin Porter Jr, Cole Anthony, and Ryan Rollins) can hold down the guard positions. 

  • SG Gary Harris – 3.0 PTS / 1.3 TRB  /0.9 AST – 52% TS / 35% 3PT
  • SG Gary Trent Jr – 11.1 PTS / 2.3 TRB / 1.2 AST – 59% TS / 42% 3PT
  • G Kevin Porter Jr – 10.3 PTS / 3.7 TRB / 3.4 AST – 53% TS / 31% 3PT (40% in MIL)
  • G Cole Anthony – 9.4 PTS / 3.0 TRB / 2.9 AST – 53% TS / 35% 3PT
  • PG Ryan Rollins – 6.2 PTS / 1.9 TRB / 1.9 AST – 60% TS / 41% 3PT

The Pros

While the financial burden of Lillard’s waive and stretch is real, the Bucks still have the potential to stay relevant for the next five years. Lillard, although talented, did not play his best basketball in Milwaukee. His decline, along with players like Khris Middleton and Brook Lopez, created an inconsistent roster that couldn’t find playoff success. Lopez and Middleton’s contracts are now off the books, which, along with Lillard’s yearly salary reduction of $40 million (stretch), opens up $90 million for the Bucks. 

  •  Khris Middleton – 33,296,000 – Washington Wizards 
  • Brook Lopez – 23,000,000 – UFA to the Clippers
  • Damian Lillard – 2 yr $112 Million stretched into 5 years – $20 million AVA

The Bucks used this available money to take a new approach in building around their Greek star. They snagged center Myles Turner from their rival Pacers on a four-year, $107 million contract. At age 29, his floor spacing and defense will pair nicely with the paint-dominant Antetokounmpo. They also acquired Kyle Kuzma (age 29) from the Washington Wizards last deadline. His size and scoring give Antetokounmpo some offensive help, but his inconsistency limits how much he can be trusted. Overall, having a strong frontcourt to hold down both ends of the floor should compensate for some of their question marks in the backcourt.  

  • Myles Turner – 15.6 PTS / 6.5 TRB / 2.0 BLK – 61% TS / 40% 3PT – $20,451,750 AVA
  • Kyle Kuzma – 14.5 PTS / 5.6 TRB / 2.2 AST – 51% TS / 33% 3PT – $22,500,000 AVA

What to Expect 

The Bucks built a team that could be elite on defense and muster up enough offense to get by. Antetokounmpo is going to put up MVP numbers, and if the role players are healthy, this team will win 45-50 games. Despite that, it’s hard to give them contender status. They have no trustworthy ball-handler and no true #2 option behind Antetokounmpo. Teams without reliable backcourts haven’t fared well in the modern NBA, and this team has the weakest guard room in the league. Bucks fans can count on another solid regular season, but a deep postseason run would require a trade deadline move or miracle development from one of their wildcard backcourt pieces. 

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