After a bold start to the offseason, the Portland Trail Blazers' starting lineup seems to be in flux (to put it gently). Joe Cronin has earned back some equity with fans as newly-drafted big man Yang Hansen thrives in Summer League, but center isn't the only position where Portland needs answers.
Portland's point guard spot -- arguably the most important position for a developing team -- will be especially competitive heading into (and possibly out of) training camp.
Any concerns surrounding recently acquired Damian Lillard's fit in the backcourt should be put on hold for the 2025-26 season as he recovers from his Achilles injury. For now, Portland must decide whether to prioritize the experience of Jrue Holiday or the potential of Scoot Henderson in their starting five. Chauncey Billups should pick the former.
Portland has a point guard dilemma
When Portland shipped out Anfernee Simons earlier this summer, they received guard Holiday in return. Holiday, a two-time champion and former lock for All-Defensive honors, is now 35. He showed serious signs of regression last season as his points (11.1) and assists (3.9) were both lows since his rookie season, a whopping 16 years ago. While one could argue those dips were the result of reduced minutes, the precipitous drop in Holiday's three-point accuracy (an elite 42.9% two years ago to a pedestrian-at-best 35.3% last season) is harder to explain.
Crazier things have certainly happened than a resurgent season for Holiday. The man is still a clampdown defender, and it's hard to imagine that three-point percentage not leveling out a bit. Still, it's safe to say that Portland mostly brought Holiday in to be an on-court mentor for its young guys (not a bad gig, considering the $104 million he's owed over the next three seasons).
The problem? The guy Holiday was brought in to mentor above all is Scoot Henderson, his exact competition for Portland's starting point guard job.
The case for Jrue Holiday to start
Heading into his third year in Portland, former No. 3 pick Scoot Henderson has yet to lose the faith of the Trail Blazers' brain trust, and especially not Chauncey Billups. But Billups knows better than anyone that point guard is the hardest position to learn. It takes time, especially at the NBA level. And if this roster has one thing, it's time.
Henderson made legitimate strides last season, perhaps not statistically, but definitely according to the eye test. There are still plenty of holes in his game, though. Remember that disastrous dip in Holiday's shooting percentage from last year? Well, Henderson averaged a nearly identical 35.4% from deep. The rest of Henderson's stats (12.7 points, 3.0 rebounds, 5.1 assists) don't much separate him from Holiday either.
Henderson has a long way to go before he's considered a bona fide starting point guard in today's NBA (a league where it seems every team has an elite player starting at the position). But again, point guard is the hardest position to learn at an NBA level, and the Portland's priority does need to be developing their young talent. But a situation where the Billups rushes Scoot into a role for which he's not yet prepared could be a nightmare for the Trail Blazers.
Plus, Portland has young players other than Henderson. Players who need a composed point guard to help them reach their potential.
Portland has a slew of young talent: Henderson, shooting guard Shaedon Sharpe, and a pair of centers in Yang Hansen and Donovan Clingan. While Henderson should still be a top priority for the team (he was the highest draft pick of all the young prospects), he is by no means their only prospect.
The development of the many has to outweigh Henderson's development alone. For this reason, Billups will eventually conclude that Jrue Holiday has to start at point guard to open the season. Holiday will play excellent defense, conduct the offense when he has to, and be a calming presence on the floor to start each game.
At least, until Scoot Henderson earns the job.