Damian Lillard’s long-time agent, Aaron Goodwin, recently suggested that the Milwaukee Bucks failed to maximize Lillard during his client’s two full seasons with the team.

“He never really had an opportunity to play as he has played the first 12 years of his career,” Goodwin told ESPN’s Jamal Collier. “He played to win in the system that he was in.”
Lillard’s scoring numbers dropped while playing for the Milwaukee Bucks. After averaging 32.2 points per game in his final season with the Portland Trail Blazers, the 35-year-old guard failed to average at least 25 points at Milwaukee, although he did win an NBA Cup with the team last December.

Two first-round exits later, the Milwaukee Bucks decided to pull the plug on Lillard by waiving and stretching his contract to make room for the free agent signing of Myles Turner for four years and $107 million.
Milwaukee Bucks Rumors: Damian Lillard almost got traded last season
In the same ESPN article, it was indicated that the Milwaukee Bucks considered trading Damian Lillard at the trade deadline last February. However, the team went on to swap Khris Middleton for Kyle Kuzma.

“The Bucks’ offseason could have taken different paths had Lillard stayed healthy — from tinkering around the margins of the roster to add a new starting center to complement a growing relationship between Lillard and Antetokounmpo or potentially trading Lillard,” Collier wrote.
“That was a last-ditch strategy, a source told ESPN, the team could have explored in effort to find another star to pair with Antetokounmpo. With Antetokounmpo in his prime, the Bucks were on the prowl for ways to improve their roster. When the opportunity to sign center Myles Turner away from Indiana presented itself, Milwaukee made the move,” he added.