According to reports, the Portland Trail Blazers are set to acquire Jrue Holiday from the Boston Celtics in exchange for Anfernee Simons and 2 second round picks.
Portland will re-acquire Holiday, whom the franchise originally received via the Damian Lillard trade in 2023, before quickly flipping him to the Celtics. That original deal saw the Trail Blazers net Malcolm Brogdon, Robert Williams III, and two first round draft picks.
Holiday is owed roughly $72M over the next two seasons, while Simons will join Boston on an expiring contract. When all is said and done, the Celtics will save approximately $40M in luxury tax payments next season.
The 26 year old Simons will likely absorb a good chunk of the shots that are now suddenly available in Boston following Jayson Tatum’s right Achilles tear. The Celtics are expected to remain active on the trade front in the coming weeks as they look to retool a roster that will likely be without their star player for the majority of the 2025-26 NBA campaign.
Simons averaged 19.3pts/0.9stl/4.8ast/2.7reb per game for Portland last season. The 6’3″ shooting guard isn’t afraid to launch it from deep, averaging nearly 9 three point attempts per contest over the last 3 seasons out west.
Meanwhile, Holiday is set to join a Trail Blazers team that has aspirations of shedding the mantle of “perennial lottery team” next season. From January 19th onwards, Portland went 23-18, and ranked third across the NBA in defensive rating. A streak that ownership will hope the team can build on heading into the fall.
A veteran of over 1,000 NBA games, Holiday has averaged 15.8pts/1.4stl/6.2ast/4.2reb since debuting in 2009 with Philadelphia. The 2x NBA champion has earned 3x All-NBA first team defence awards, and 3x All-NBA second team defence selections since 2018, cementing his status as one the league’s premier defenders at the guard position.
In Holiday, Portland acquires a true point guard, and likely frees up some additional looks for budding stars Scoot Henderson and Shaedon Sharpe now that Simons’ shot volume has been removed from the equation.
Both clubs will now turn their attention to the NBA Draft which kicks off on Wednesday June 25th at 8pm ET.
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