The Milwaukee Bucks made a high-stakes decision this offseason by waiving and stretching the contract of injured point guard Damian Lillard in an effort to maintain their focus on keeping nine-time All-Star forward Giannis Antetokounmpo. This move aims to create cap space despite the team’s limited draft assets and financial flexibility. With Giannis’ contract set to expire in two years, the Bucks acted to remain competitive while hoping to secure his long-term commitment.
Giannis Antetokounmpo has remained loyal to Milwaukee despite reports suggesting he has considered his future with the franchise. His dedication led to an NBA Championship in 2021; however, the Bucks have faced disappointing playoff results ever since, exiting in the first round for two consecutive seasons.
Challenges Loom as Bucks Face Injuries and Playoff Disappointments
Adding to the uncertainty, Damian Lillard suffered a torn Achilles late in the recent playoffs, leaving him out for the upcoming season. This injury complicated the Bucks’ already precarious position as they look to avoid another early playoff elimination. Despite Lillard’s absence, the team surprised observers by waiving him and stretching the $113 million remaining on his contract over five years.
Fred Kratz of The Athletic described this tactic as a risky financial gamble.
“In early July, the Milwaukee Bucks waived and stretched All-Star point guard Damian Lillard’s contract,”
Kratz wrote.

“Lillard wasn’t going to help them next season as he recovers from a torn Achilles, and the Bucks were desperate to add talent with Giannis Antetokounmpo’s contract up in two years.”
Kratz further explained the financial implications:
“Milwaukee waived Lillard, then stretched the $113 million left on Lillard’s contract over the next five seasons, which comes out to almost $22.5 million of dead money on their books every season through 2030.”
He also highlighted how unusual this move is for a player with such a large remaining salary.
“Typically, this mechanism has been used for lower-salaried players, not ones owed anything close to as much as Lillard or Beal. The reason why: It’s not safe. The Bucks and Suns will owe money to players not on their roster through the end of the decade, harming their flexibility in the process,”
Kratz noted.
Concerning the urgency behind the move, he added,
“The Bucks were desperate to stay competitive while Antetokounmpo remains in Milwaukee.”
New Additions Aim to Boost Milwaukee’s Roster Amid Financial Constraints
With the salary cap relief gained from Lillard’s contract stretch, the Bucks acquired center Myles Turner, a starting-caliber player who fits the team’s needs, and guard Cole Anthony, who brings needed ball-handling skills. These moves provide fresh options and help the Bucks maintain their competitive edge as they try to build around Giannis.
Despite these roster improvements, external observers remain skeptical about the team’s ability to make a significant playoff impact in the coming season. The Bucks’ front office appears to be betting that these changes, combined with managing finances aggressively, will offer the best chance to secure Giannis’ continued presence and push deeper into the postseason.
Implications for Giannis Antetokounmpo’s Future and Team Success
The decisions made by Milwaukee’s management reveal the high stakes involved in keeping their franchise player, Giannis Antetokounmpo. By committing to financially risky strategies, the Bucks are signaling their determination to build a competitive team despite limitations in draft assets and salary cap flexibility.
How well the additions of Myles Turner and Cole Anthony will translate to playoff success remains to be seen, but the looming dead money from Lillard’s contract may restrict future moves. The franchise’s ability to navigate this challenging period will be critical in securing Giannis’ long-term stay and achieving greater postseason results.
Fans and analysts alike will be closely watching whether these bold decisions can reverse recent playoff failures or if the Bucks face further uncertainty around their star’s commitment in the coming years.
