On the surface, trading one guard for another in the Anfernee Simons-Jrue Holiday swap defeats one key purpose of trading away Simons in the first place. The Portland Trail Blazers needed to figure out their backcourt hierarchy and clear the path for former top ten picks Scoot Henderson and Shaedon Sharpe.
It may not seem like it at first, but the Blazers accomplished exactly that when they acquired Holiday. His presence as a 3-and-D guard in the backcourt could result in breakout seasons in 2025-26, particularly for Henderson.
Jrue Holiday clears the path for Scoot Henderson's breakout
At this stage in his career, Holiday isn't as much of a playmaker as Simons. Last season in Boston, Holiday averaged 11.1 points and 3.9 assists with a usage rate of 15.9. Compare that to Simons' season in Portland, who had 19.3 points and 4.8 assists with a 24.6 usage rate (second highest on the team), and it's easy to see why general manager Joe Cronin made this swap from a developmental standpoint. Holiday is taking a step back, which should help increase Henderson's on-court production.
Henderson will not only have an expanded role as a result of this trade, but he'll also be gaining another valuable mentor in Holiday.
In his introductory media availability, Holiday said he was ready to embrace the role of Portland's veteran "jerk," much like Andre Iguodala had done with him during his rookie season with the Philadelphia 76ers.
"He was a jerk. My rookie year, he was just on me. He was on me about a lot," Holiday said. "And I didn't really understand why until later. He obviously saw something in me that I guess I hadn't seen yet. And just constantly being on me and harping on me about being consistent and things that I have to do were super important."
Holiday also referred to Henderson as "the next one up," meaning he could see something in Scoot and provide similar mentorship as Iguodala did for him in 2009.
Between Holiday, Lillard, and Chauncey Billups, Henderson couldn't be surrounded by a more ideal trio of guard mentors. He's set to take that next step as a rising star in the league.
Henderson quietly showed signs of improvement last season, but they didn't jump out statistically as he wasn't made as much of a priority as he should've been. Despite investing a No. 3 overall pick in Henderson, Portland made him an afterthought in the offense, decreasing his minutes and usage rate from his rookie season. They're finally righting the ship in 2025-26 with the addition of Holiday and subtraction of Simons.
Everything is aligning for a breakout season for Henderson, and it couldn't have come at a better time, as Portland desperately needs more backcourt clarity.