The Portland Trail Blazers sent Anfernee Simons to the Boston Celtics in a trade for Jrue Holiday. The veteran’s arrival could be a problem for the Blazers and young guard Scoot Henderson in Chauncey Billups’ system.
The Trail Blazers have had many talented guards play in the Pacific Northwest. Damian Lillard headlines that group of players, but they also had Simons and Henderson as his successors. Unfortunately, the Blazers have had a logjam at point guard since Lillard left.
The first issue was Simons getting in Henderson’s way, leaving the former G League Ignite guard to come off the bench. Now that Simons is on the Celtics, Henderson should have a pathway. However, Holiday was the other piece in the trade, and he plays at the one spot.
Although Holiday is 35, he remains a productive point guard. In 62 games in the 2024-25 season, he averaged 11.1 points, 4.3 rebounds, and 3.9 assists. That is still an impressive stat line, especially since he also plays elite defense.
Throughout Billups’ four-season stint with the Trail Blazers, he has favored the veteran. That happened with how he used Simons in front of Henderson and his reliance on Jerami Grant. Due to the latter’s injuries, Toumani Camara and Deni Avdija received starter minutes, but that’s another positional logjam.
In 2025-26, Henderson should be a starter. He is entering his third season, and as a top prospect in the 2023 NBA Draft, he deserves starter minutes. With Holiday on the team, that might not happen due to the expectations set by his three-year $104 million contract.
Portland can buck the trend and make Holiday come off the bench, but that might make him disgruntled. Billups’ plan for Holiday must strike a balance between being a productive player and a mentor to the younger guard.
Everyone already knows that Henderson had a tough rookie season, and that hurt his reputation. During his sophomore season, he played behind Simons, but he made the most of every opportunity.
In 10 games as a starter during the 2024-25 season, Henderson averaged 16.2 points, 6.5 assists and 3.2 rebounds. That is an impressive stretch, and he was efficient, shooting 47.5% from the field and 43.6% from distance. If Billups chooses Henderson as the Blazers’ point guard, we will see an improved version of him.
Henderson will be more confident, as he knows the coach trusts him. Billups has already stated that he wants Henderson to keep working during the offseason. That is already happening, as the young point guard had a training session with five-time NBA champion Derek Fisher.
Scoot pracuje nad rzutem z Derekiem Fisherem pic.twitter.com/OY14mlCnjo
— Lillard93 (@Lillard93) July 10, 2025
Portland had a promising 2024-25 campaign, but the Blazers are still a rebuilding team. Henderson is crucial for this long-term plan, as he and Shaedon Sharpe are the long-term backcourt. They could compete for a spot in the postseason soon, but that does not require starting Holiday.
If Henderson can showcase why he is a deserving starter, the Blazers have a star player to build around. With Sharpe as his partner, Portland will have a dynamic backcourt. They already have some crucial pieces, like a versatile defender like Camara and a high-potential center like Donovan Clingan.
They even went for an upside selection in the 2025 NBA Draft when they selected Yang Hansen with the No. 16 pick. Portland is doing a lot of good things; they only need to confirm their foundational point guard.
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