Bucks regret – Milwaukee’s rebuilding years trace back to a 2023 trade that sent Jrue Holiday out and brought Damian Lillard in. Holiday’s production, defense, and leadership—averaged over three seasons, capped by All-Defense and an All-Star nod in 2023—show how far the Buck
When the Bucks traded Jrue Holiday away to make room for Damian Lillard, the mistake wasn’t obvious in the moment. The plan sounded clean: add a superstar point guard to raise the team’s playoff offense.
But the season that followed told a harsher story. Milwaukee’s perimeter defense struggled without the former lockdown stopper it had counted on at the point of attack. The Bucks didn’t just lose a guard who could fill a stat sheet; they lost a defensive foundation.
Holiday had spent three years as Milwaukee’s starting point guard. and during that stretch he averaged 18.5 points. 4.7 rebounds. and 6.8 assists per game. His impact wasn’t measured only in numbers. He was an All-Defensive selection every year he played in Milwaukee. In 2023, he also became an All-Star.
That’s the part Milwaukee can’t easily replicate now. After the trade for Lillard. the Bucks’ backcourt slid into a cycle of “maybe” players—guards the team hopes it can move again. The fall has been incremental, but it’s still a fall. The franchise’s situation and Giannis Antetokounmpo’s reported disillusion with the team are now often tied to that decision—specifically. the choice to include Holiday in the 2023 trade for Lillard and the way it shaped the years that followed.
The trade itself was built around bringing in Lillard, described as an All-NBA point guard, to boost Milwaukee’s playoff offense. Holiday was the piece that left. And in hindsight, the key problem was how much the Bucks underestimated what he provided on defense.
Milwaukee could have had a backcourt built around both Lillard and Holiday, with Giannis Antetokounmpo still anchoring the roster. Holiday can play the shooting guard spot as well as point guard. and the argument has always been that pairing him with Lillard would have offered more defensive stability—and enough shooting—to make the offense work.
Now the Bucks find themselves searching for their next version of Holiday, but the roster doesn’t hold a match. They do have guards. but they can’t count on any one of them to deliver Holiday’s production and leadership. The closest figure mentioned is Ryan Rollins—a strong defender with promising offensive upside.
Still, the gap is clear. Getting Rollins to Holiday’s level in Milwaukee would be a tall task. And even if that development arrives, putting together the right entire team to compete for a title is even harder.
Holiday’s next step after leaving Milwaukee also offers a contrast that Milwaukee leadership has to live with. The very next season after the trade, he won a title with the Celtics. That championship came while he played more of an off-ball role, a reminder that he can win in multiple systems.
If Milwaukee needed a blueprint for what it gave up, the Boston title was it. Holiday’s versatility has been a defining strength. and that Celtics success—right after departing Milwaukee—stands as a sign of what the Bucks may never be able to replace exactly. only build around through time. patience. and smarter alignment.
For a franchise trying to climb out of rebuilding, the lesson isn’t just that trading Holiday changed the lineup. It’s that the Bucks didn’t just trade a guard. They traded away a defensive constant. a steady leader. and a two-way player whose value showed up immediately once he was gone—and kept showing up elsewhere after he left.
Bucks Jrue Holiday Damian Lillard Giannis Antetokounmpo Milwaukee Bucks trade NBA playoffs Celtics title Ryan Rollins NBA All-Defense All-Star 2023