The Portland Trail Blazers appeared to have righted the ship following a down 2021-22 season following Damian Lillard's season-ending abdominal injury. Adding Jerami Grant to a Lillard, Anfernee Simons, and Jusuf Nurkic-led core looked like a stroke of genius, especially as the Blazers came out of the gates scorching hot.

However, the all-too-familiar apparition of Blazers injury woes came to haunt them once more. Lillard missed a stretch of games, and the Blazers blew a few winnable games against tough opposition as they slowly tumbled down the congested Western Conference playoff picture.

Damian Lillard's presence alone guarantees that the Blazers remain semi-competitive nonetheless. Thus, despite their drop-off, they very much remain in the thick of the playoff hunt. If anything, the Blazers needed to add depth, particularly on the frontcourt, with Jusuf Nurkic currently nursing a calf injury. That should help Portland maximize Lillard's stellar play as of late, as Dame has been carrying the franchise he so loves on his back in a manner reminiscent of his carry job during the 2019-20 campaign.

Instead, the Blazers decided to semi-punt on the season, trading away two valuable role players in Josh Hart and Gary Payton II for a haul of Cam Reddish, Kevin Knox, Matisse Thybulle, a 2023 first-rounder from the New York Knicks, and a plethora of second-round picks.

While Thybulle could be a useful defensive piece alongside Lillard, Reddish and Knox have both failed to impress at their previous stops. These three, simply put, are not better players than either Hart or Payton. The picks they received are helpful for sure. But for a Blazers fan, it's hard to come to the conclusion that their team got better following these trades.

Nevertheless, selling off on Josh Hart (an impending free agent) and Gary Payton II (a recent free agent acquisition) aren't bad moves on their own. But a closer look towards the Blazers' dealings show that they made a serious blunder amid all the trade noise.

Blazers 2023 NBA trade deadline mistake: Failing to disclose the true severity of Gary Payton II's core injury

Following a strong 2021-22 season with the reigning champion Golden State Warriors, Gary Payton II, a man who has bounced around the fringes of the NBA for so long, was able to secure a three-year, $26 million deal with the Blazers. The Warriors did not want to let Payton go; his defense, hustle, and timely shot-making all proved valuable as the Warriors unexpectedly claimed their fourth ring of the past decade.

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The Houston Rockets invested heavily into Fred VanVleet during the 2023 offseason. Houston gave the point guard a three-year, $128 million deal in a move that was meant to turn the Rockets from a rebuilding team into a championship contending one. The signing did just that, as the Rockets finished the 2024-25 regular season as the two-seed in a stacked Western Conference. VanVleet was the veteran presence and 3-point shooter that the team desperately needed, and he still might have a role with the Rockets going forward. Houston has a team option on his contract for next year, and they very well may pick it up. The Wichita State product reportedly wants to stay in Houston, but the point guard would be set to make over $44 million next season under his current contract. The Rockets and their guard recently pushed back the deadline on Houston's decision with VanVleet, and although reports suggest that they are interested in writing up a new, long-term deal, it isn't necessarily a guarantee that VanVleet will be playing for Houston next year. The Rockets blew him away with an offer he couldn't refuse back in 2023, and another team could so the same when/if he hits the open market this offseason. If VanVleet does become an unrestricted free agent, which teams outside of Houston would make the most sense for him to sign with? 1. Orlando Magic Jalen Suggs and Franz Wagner recently signed big deals with the Orlando Magic, and Paolo Banchero will be getting a mega contract extension here soon. Because of that, the Magic no longer have money to blow like they have had in recent years. That will make a deal for another big ticket free agent hard to pull off, especially considering the team signed Kentavious Caldwell-Pope last year. If Orlando can make the money work, though, then Fred VanVleet would be a great fit with the Magic. The Magic finished dead last in 3-point shooting this season, and VanVleet has made at least 2.5 deep balls per game in every season since 2018-19. VanVleet can hit shots form behind the arc off of the bounce or in catch-and-shoot situations. The Rockets were heavily reliant on his shooting expertise, so the guard would have plenty of familiarity getting up deep shots with high volume if he signed with the Magic. While undersized, VanVleet is a pesky defender, so he'd fit right in with a Magic team that has one of the best defensive units in the league. VanVleet could play alongside Suggs and give opposing teams fits. Ultimately, though, the Magic just need more shooting to get to the next level, and VanVleet is arguably the best shooter who could be available on the open market this offseason. 2. Brooklyn Nets A more realistic option for a VanVleet destination would be the Brooklyn Nets. The Nets are set up to have the most cap space this offseason, and they have a major need at point guard. With D'Angelo Russell and De'Anthony Melton hitting free agency this offseason, the Nets don't have a true point guard under contract for next season. Brooklyn needs to spend big this offseason, and they'd be smart to offer VanVleet a contract big enough that he'd have no choice but to leave Houston. VanVleet averaged 14.1 points per game last season, which was his lowest mark since 2018-19. He is trending the wrong way, but he still has enough left in the tank to give the Nets a few good seasons. 3. Portland Trail Blazers In the same way that the Rockets were looking to take the next step in 2023, the Portland Trail Blazers could use VanVleet's presence to get over the hump. The Trail Blazers have plenty of big man depth, as centers Deandre Ayton, Donovan Clingan, Robert Williams, and Duop Death are all under contract next season. Portland also has a lot of wing depth. Deni Advija started to look like a star late this past season, Toumani Camara is an elite defender, Shaedon Sharpe is a freakish athlete, and Jerami Grant is a proven scorer. The team is thinner in the backcourt, though. Anfernee Simons is a solid scorer, but Scoot Henderson has looked like a fringe draft bust since being drafted third overall. Portland shouldn't give up on Henderson completely, but there wouldn't be any harm in signing another guard. Like the Magic, the Blazers were one of the worst 3-point shooting teams in the NBA. VanVleet would improve that weakness, and in a stacked Western Conference, Portland needs all of the help they can get if they are to compete for a playoff spot.
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All in all, landing with the Blazers was far from the worst outcome in the world for the 30-year old guard. For a team built around two score-first guards, Payton's defense-first game was sure to play a prominent role. Never mind that Payton missed the Blazers' first 35 games due to a core muscle injury; once he was off the mend, he was sure to provide a spark the Blazers so desperately need.

And for the most part, Payton has done what the Blazers thought he would do when they signed him. But with the Blazers deciding to recoup assets for some pieces that don't make too much sense for a middling team, it wasn't the worst idea in the world for Portland to give up on their offseason acquisition not even a year after signing him.

But that's where crap starts hitting the fan. Shams Charania of The Athletic reported that Payton failed his physical with the Warriors; the difference between the Dubs and the Blazers' evaluation of the 30-year old guard's health was night and day. The Warriors' medical staff couldn't fathom how Payton was playing through the injury while Blazers general manager Joe Cronin said that they wouldn't allow him to play if he wasn't medically cleared.

As a result, the trade is now at risk of being scrapped altogether. That won't be a good outcome for any team involved in the four-team trade. It's hard to imagine the Warriors, Detroit Pistons, and Atlanta Hawks jumping for joy following this unfortunate turn of events.

Of course, this is not to say that the Blazers did this on purpose. But it's difficult to feel too much sympathy for the Blazers in this scenario. If the reports are correct and the Blazers, indeed, were forcing Payton to play through the pain by making him take a strong painkiller called Toradol, then that is malpractice. There's no use in sugarcoating things.

Not only might this put off prospective trade partners in the future, it might also further dampen the Blazers' chances of acquiring impact players via free agency. After all, who would want to play for a franchise that might be putting their players at risk of further injury?