Damian Lillard finds himself confronted with a familiar postseason challenge he believed he had left behind with his move to the Milwaukee Bucks.

Lillard’s aspirations for an NBA championship are now at risk following Giannis Antetokounmpo’s calf injury during the Milwaukee Bucks’ victory over the Boston Celtics. Antetokounmpo’s return hinges on the speed of his calf’s recovery, as there’s relief it’s not a more severe Achilles injury.

This unfortunate timing for the Bucks, with just two games remaining before the playoffs, raises concerns about their readiness without Antetokounmpo and Khris Middleton operating at full capacity, despite their current standing as the Eastern Conference’s second seed.

For Lillard, who joined forces with the former league MVP after over a decade leading the Portland Trail Blazers, this setback is disheartening. His move to Milwaukee was anticipated to significantly boost his chances for a title.

Yet, the synergy between Lillard and Giannis hasn’t materialized as expected, and the Bucks don’t exude the dominance they’ve held in the East over the last four seasons.

This predicament echoes Lillard’s experiences in Portland, where he often grappled with roster limitations, notably during the 2019 playoffs without key players like Jusuf Nurkic.

On an individual level, Lillard’s shooting performance has dipped, paralleling the Bucks’ collective effectiveness.

Looking ahead, if the playoffs commenced immediately, Milwaukee would confront either the Philadelphia 76ers or the Miami Heat, pending the Play-In Tournament’s outcome. Both pose formidable challenges, especially considering the Heat’s historical advantage over the Bucks in recent postseasons.

While Lillard has displayed success against key opponents like Joel Embiid and Jimmy Butler in recent matchups, his playoff prospects still hinge on his team’s overall strength to contend against tough Eastern Conference rivals and vie for the championship in June.