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Milwaukee Bucks to Get Some Salary Cap Relief After Damian Lillard Returns to Portland Trailblazers

Originally posted on WI Sports Heroics | By Robin M Adams | Last updated Jul 17, 2025 9:06 PM ET

Nearly two years ago, the Milwaukee Bucks sent Jrue Holiday and multiple draft picks to the Portland Trailblazers for now nine-time NBA All-Star point guard Damian Lillard. The move shocked the NBA world, mostly because everyone believed the Miami Heat was the only team Lillard had any interest in playing for. It also excited Bucks fans (though they were saddened to see Holiday leave) because it meant Lillard and Giannis Antetokounmpo would combine to form one of the league’s most dynamic duos.

And while Lillard and Giannis did dominate the regular season in each of the two seasons that they were teammates, they barely saw the floor together in the NBA Playoffs. Giannis was injured near the end of the 2023-24 regular season and missed Milwaukee’s entire opening round loss to the Indiana Pacers.

Lillard, who missed weeks due to blood clots towards the end of the 2024-25 season, tore his Achilles during the team’s first round loss to Indiana this past postseason.

The Milwaukee Bucks Waived Damian Lillard, Who Will Return to the Portland Trailblazers

Milwaukee Bucks to Get Some Salary Cap Relief After Damian Lillard Returns to Portland Trailblazers 1 Feb 6, 2023; Portland, Oregon, USA; Portland Trail Blazers guard Damian Lillard (0) drives the lane against Milwaukee Bucks guard Jrue Holiday (21) in the second half at Moda Center. Mandatory Credit: Jaime Valdez-USA TODAY Sports

After Lillard’s injury, the Bucks were faced with the tall task of building a competitive roster around Giannis without much salary cap space to work with. Even though trading Khris Middleton during the year last season helped bring them under the second apron, they still had no room to sign external free agents to anything other than veteran minimum deals.

With Lillard likely out for most, if not all, of 2025-26, and with it becoming increasingly obvious that he would not pick up his player option for 2026-27, the Bucks decided to waive the nine-time All-Star, and stretch out his $112 million cap hit over the span of five seasons.

In doing so, they agreed to pay Lillard a little over $22 million a year, but saved tens of millions of dollars on the salary cap, taking them below the threshold and giving them the ability to sign Myles Turner and several of their own free agents.

On Thursday, it was reported that Lillard was returning to the Trailblazers on a three-year $42 million contract. This decision made sense as he was never shy about how hard being so far away from his kids was while he was with the Bucks. Now he gets to end his career with the team that drafted him and with whom he spent 11 seasons. He also gets to be there for his family.

The Milwaukee Bucks Will Get Some Small Salary Cap Relief After Damian Lillard Signed with the Portland Trailblazers

Milwaukee Bucks to Get Some Salary Cap Relief After Damian Lillard Returns to Portland Trailblazers 2 Apr 25, 2025; Milwaukee, Wisconsin, USA; Milwaukee Bucks guard Damian Lillard (0) reacts after making a basket against the Indiana Pacers in the second half during game three of first round for the 2024 NBA Playoffs at Fiserv Forum. Mandatory Credit: Michael McLoone-Imagn Images

According to ESPN’s Bobby Marks, Lillard’s deal with Portland will also save Milwaukee some money, albeit not a lot, on their salary cap in each of the next five seasons.

The set-off is applied after the season pic.twitter.com/TylOjkywTO

— Bobby Marks (@BobbyMarks42) July 17, 2025

As one can see from the graphic above, Lillard’s cap hit over the next five seasons went from $22.5 million a year down to $20.2 million, a savings of $2.3 million annually.

And while that may not seem like a lot (and it isn’t), the Bucks can use every bit of salary cap relief possible as they continue to try and build competitive rosters around Giannis.