ESPN polled 20 coaches, scouts, and executives around the league to get their opinions on how the NBA offseason played out. The Portland Trail Blazers made an appearance on the survey, but for all the wrong reasons.
The Blazers received one vote for having the worst overall offseason and one vote for having the most surprising move, acquiring veteran Jrue Holiday in exchange for Anfernee Simons. That specific trade received criticism around the league, as Portland received three votes for making the worst move of the summer. That was tied with the Phoenix Suns (waiving and stretching Bradley Beal) for second, only behind the Pelicans, who recklessly traded an unprotected pick swap.
"I just don't get what they are trying to do," a West assistant coach said, via ESPN. "You can't get enough time for all of their guards."
Portland will regret the Jrue Holiday trade
Simons was a trade candidate for multiple seasons with the Blazers. He didn't fit their defensive identity and wasn't impactful enough as a two-way player to justify his next contract. Most significantly, Portland needed to clear the path for their recent top ten picks, Scoot Henderson and Shaedon Sharpe.
While Holiday is a better fit defensively, he's still an overpaid guard getting in the way of Portland's young guards. Portland was right to trade Simons, but they should've been looking more towards the future, acquiring draft capital and long-term assets. Instead, they made a win-now move, swapping one problem for another.
Of course, there are positive takeaways from this trade, too. Holiday is a perfect mentor for Portland's youth, and it's already apparent that he's embracing that veteran role before even playing a single game for the Blazers. He's also lower maintenance than Simons, particularly in terms of usage rate. So, although he's likely taking away a starting spot from the very players he was brought in to help unlock, Henderson and Sharpe should still be seeing relatively increased roles and touches compared to last season.
While this wasn't the worst offseason move, it does deserve to receive votes. The main question is just... why? The Blazers are giving their fans headaches at this point as they unnecessarily traded one backcourt dilemma for another. In the stacked Western Conference, their ceiling is a play-in team.
It will only get more difficult to upgrade (and retain) their roster with Holiday and Jerami Grant on the books for multiple years. This was a one-step-forward, two-steps-back type of move that Portland didn't need to make. Add in the fact that Damian Lillard is back with Portland, providing similar veteran leadership for significantly cheaper, and you can't help but wonder if the Blazers will come to regret this overly aggresive move.