The Trail Blazers' revised swap of Anfernee Simons for Jrue Holiday could be disastrous for their long-term outlook, and Portland's lack of patience in their rebuild approach is to blame.
According to NBA insider Jake Fischer, the Boston Celtics are having difficulty finding a trade partner to flip Simons and appear to be heading into the 2025-26 season with him still on their roster. That said, we'd still much rather be in Boston's situation than Portland's regarding which guard to have.
Simons is on an expiring $27.7 million contract, while Holiday is currently set to be the Blazers' highest-paid player on a three-year, $104 million deal. He's already 35 years old and has shown signs of declining play, averaging 11.1 points and 3.9 assists last season.
Jrue Holiday trade exposes Blazers' roster-building flaw
Portland must extend its young core in the coming seasons, notably Toumani Camara, Shaedon Sharpe, and Scoot Henderson; this could be challenging to navigate under the new CBA with Holiday and Jerami Grant on the roster. They'll be ready to compete in the Western Conference by the 2027-28 season with an ascending young core. However, they will also have difficulty upgrading their roster externally as they will have to pay 37-year-old Holiday $1 million for every year he's been on planet Earth.
Maybe this all works out, and Portland can flip him yet again, getting more value than Simons' grim market appears to be. But the risk doesn't outweigh the reward for Portland, as Holiday could soon be viewed as a negative asset, if he isn't already.
Holiday is still an impactful two-way player with championship experience. But it made much more sense for a contender to trade for him -- a team that was a piece away and willing to sacrifice their financial flexibility to get them over the top.
Portland may have been a Holiday piece away from a play-in spot. That experience can be valuable for a young core; then again, Holiday will also likely be blocking a starting spot from said core, essentially defeating the purpose.
Although the Blazers could've shipped Simons earlier when he had more value, they were wise to trade him rather than committing to a long-term extension, which would've limited their ceiling and flexibility. Another reason to trade him was to clear the runway for Henderson and Sharpe in the backcourt.
But these issues haven't been solved with Holiday in the mix -- they're just overpaying for a different, older guard.
Joe Cronin may believe that Portland's youth is ready to catch up to Holiday's timeline after their surprising midseason turnaround. New ownership on the horizon could also play a role in their aggressive win-now moves. However, whether the Holiday trade was driven by an overly optimistic GM or external pressure, both reasons stem from Portland's lack of patience. The unnecessary rush to accelerate Portland's rebuild threatens to trap them in purgatory.