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Jrue Holiday realization keeps burning Bucks in worst possible way

The Bucks desperately need someone just like Jrue Holiday.
Portland Trail Blazers guard Jrue Holiday (5) reacts during warmups before the game against the Charlotte Hornets at Moda Center on Mar 10, 2026.
Portland Trail Blazers guard Jrue Holiday (5) reacts during warmups before the game against the Charlotte Hornets at Moda Center on Mar 10, 2026. | Jaime Valdez-Imagn Images

Former Bucks guard Jrue Holiday has been thriving this season on the Trail Blazers and it's adding regret to Milwaukee's original decision to trade him.

Since the All-Star break, Holiday is averaging 19 points, six assists, and four rebounds per game while shooting an efficient 51 percent from the field and 42 percent from three. His incredible play has rubbed salt into the wound of yet another poor Bucks decision in recent seasons.

The Bucks should have never traded Jrue Holiday

Holiday was a mainstay on the Bucks for years and played a key role in the 2021 championship squad. But he was dealt in a shortsighted move to land All-Star Damian Lillard in 2023. Lillard never found his groove or postseason success during his two years in Milwaukee and has now rejoined the Blazers along with Holiday.

Holiday originally ended up on the Celtics, where he won another championship in 2024. But they also chose to dump him and get off his contract with fears of age-related decline. Instead, he's bounced back in a major way as a reliable 3-and-D point guard. His defense remains strong as usual, and his 3-point shooting has been exactly what every team needs.

If the Bucks had kept Jrue Holiday this whole time, they might have found more playoff success in recent seasons. Certainly, they would have better talent right now that could help them compete for a playoff spot rather than looking ahead to the draft. Holiday is succeeding on a Blazers team without the best talent around him, but his skill set is adaptable to any situation.

Jrue Holiday is a perfect fit for any team

Holiday's versatility lets him fit into any team or roster. The Bucks could use him as a play initiator, shooter, and perimeter defender. He's more than solid on both ends of the ball, so there are no true downsides to having him on the floor.

Additionally, he would be a great mentor for the Bucks' young guards. Both Ryan Rollins and Kevin Porter Jr. are coming into their own as Milwaukee's future backcourt, but could use more guidance from their teammates. Having someone with a diverse skill set and experience in different roles, like Jrue Holiday, would do wonders for their development.

No matter where he goes, Jrue Holiday keeps proving teams wrong when they trade him. His contract might be hefty, and he might be 35 years old, but he's still worth the cost. He's become an ageless wonder with a highly skilled game and resilient athleticism, on top of his 17 seasons of experience. Given the Bucks' current state and recent misfortunes, no one regrets trading Holiday like they do.

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