Tue Jun 24 20:00:00 UTC 2025: ## Bucks Alumni in Motion: Middleton Stays Put, Holiday on the Move (Again)

**Milwaukee, WI** – Two familiar faces from the Milwaukee Bucks’ recent championship past find themselves in contrasting situations this offseason. Khris Middleton, a key member of the 2021 title team, will remain with the Washington Wizards after picking up his $34 million player option, ESPN reports. Meanwhile, Jrue Holiday, another vital piece of that championship puzzle, is headed to the Portland Trail Blazers in a trade with the Boston Celtics, according to USA TODAY.

Middleton, who was traded to the Wizards in February after over a decade with the Bucks, will look to contribute to a rebuilding Washington squad that finished with the worst record in the Eastern Conference last season. The three-time All-Star’s tenure with the Wizards was hampered by a knee injury, limiting him to just 14 games. Despite his recent injury struggles, Middleton’s legacy in Milwaukee remains secure, ranking among the franchise’s all-time leaders in points, games played, and three-pointers made.

Holiday, on the other hand, finds himself on the move once again. Just two seasons removed from helping the Celtics secure their own NBA championship, Holiday is being traded to Portland in exchange for guard Anfernee Simons and two second-round draft picks. The Celtics are reportedly looking to shed salary ahead of the NBA Draft and free agency. Simons will bring scoring punch to the Celtics with Jayson Tatum likely out for the season.

This marks the second time Holiday has been traded to Portland. He was initially sent to the Trail Blazers by the Bucks as part of the Damian Lillard trade in September 2023, only to be rerouted to Boston four days later. Holiday had previously signed a four-year, $134.4 million extension with the Celtics, leaving his future with the Blazers uncertain. It is to be seen whether Holiday will remain in Portland or whether he will be traded again.

Holiday, acquired by Milwaukee in 2020, played a crucial role in the Bucks’ 2021 championship run, forming a formidable trio alongside Giannis Antetokounmpo and Middleton. His tenacious defense and impactful plays endeared him to Bucks fans during his short time in Milwaukee. His future remains uncertain as the offseason continues, but his legacy in Milwaukee will endure.

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