7 NBA Teams That Waited Too Long to Trade Their Stars

Trading away NBA stars is often viewed as a disastrous last resort. But you know what can be even worse? Waiting too long to move franchise cornerstones.

Stubbornness when it comes to moving on is almost always understandable. Superstars are championship currency, and finding another one is difficult. There is also an emotional component to overcome, particularly if the player-team marriage previously resulted in a championship.

Sometimes, though, the writing isn't just on the wall. It's etched into concrete.

Situations change. Players request trades—or signal a desire for change indirectly. A franchise's championship outlook can fade with no obvious route back. Priorities shift. And so on.

Any of these cues should mark the end of a star's tenure. But as we're about to see, things don't always play out that way.

Note: We focused only on stars whose first NBA teams waited too long to move them, and limited the scope to trades made after 2020. Each player will be presented in chronological order of when they were moved, with the date determined by the first report rather than official transaction completion.

Philadelphia 76ers: Ben Simmons (February 2022)

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If you think this is about the Philadelphia 76ers not moving Ben Simmons immediately after he passed up a wide-open dunk in Game 7 of the 2021 Eastern Conference semifinals, well, you're right.

But it's not just about that.

Philly reportedly felt like it needed to choose between Simmons and Jimmy Butler in 2019. It's safe to say the Sixers chose poorly.

The decision to keep Simmons was never that cut and dry. He and Joel Embiid were far from the most intuitive offensive fit. The Sixers rolling with Simmons over Butler merely weeks after experiencing firsthand how much championship influence superstar two-way wings have is so bananas that it's actually impressive.

Strike that from the record, and Philly still let the entire Simmons holdout saga drag on for too long. Then-lead executive Daryl Morey received credit for embracing the awkwardness and using Simmons to land James Harden. But that argument rings incredibly hollow when looking at how that entire experiment ended.

Oh, and then there's the entire matter of the Sixers potentially (probably?) turning down a package from the Sacramento Kings that featured Tyrese Haliburton and was offered during Simmons' time away from the team.

Even if that offer was never on the table, Philadelphia still had other potential avenues to explore rather than committing to the ultimately underwhelming Harden path.

Portland Trail Blazers: Damian Lillard (September 2023)

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Damian Lillard and the Portland Trail Blazers both suffered from their collective refusal to act. The ground shifted beneath them long before he signed a two-year, $112.6 million extension in 2022, but neither side seemed like they wanted to be the one to initiate breakup talks.

In typical romcom fashion, the miscommunication blew up in everyone's faces.

Granted, more harm was done to Lillard. Remaining in Portland so long cost him a handful of opportunities to contend elsewhere had he forced the issue. And in the end, he was sent somewhere not on his initial list of preferred destinations.

Meanwhile, the Blazers wound up securing what has since become a solid return: Deandre Ayton; Toumani Camara; Milwaukee's 2029 first-round pick; swap rights with Milwaukee in 2028 and 2030; and Jrue Holiday, who they in turn flipped for Robert Williams III, Malcolm Brogdon, Boston's 2029 first-round pick and a 2024 first-rounder (Bub Carrington) they used in the Deni Avdija trade.

This doesn't excuse the process. The Blazers could have gotten more outright first-rounders had they acted sooner. And we should not discount the extra bites at the apple. Those Bucks picks still look good, but lottery reform dims some of the sheen.

More than anything, it was an unsatisfying way for Lillard and the Blazers to part ways. He later found his way back to Portland in another quintessential romcom move. But the toxic standoff between him and the Blazers, as well as the noxious rivalry between Miami shills and Portland fans, could have been avoided.

Toronto Raptors: Pascal Siakam (January 2024)

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For as much as many of us worship at the altar of Masai Ujiri, the former Toronto Raptors president racked up quite a few Ls while leading the post-championship charge. The timing of the Pascal Siakam trade ranks among the biggest.

Fans, media and blogpeople alike were calling for the Raptors to pick a distinct direction prior to the 2023-24 campaign. Scottie Barnes was entering Year 3. Fred VanVleet had bolted for the Houston Rockets in free agency. Both Siakam and OG Anunoby were heading into contract years.

Ideally, Toronto would have made tough calls on multiple players long before the 2023 offseason. Coming off a 41-win campaign and having already lost one core member for nothing, there should have been more urgency to capitalize on the value of Siakam and Anunoby if the organization wasn't going to back up the Brink's truck to keep them.

Instead, Ujiri and Co. waited until the middle of their contract years to move them.

The return on Siakam reflected the ill-conceived timing. The Raptors landed Bruce Brown Jr., Kira Lewis Jr., Jordan Nwora, a 2024 first-round pick (Isaiah Collier) that they flipped as part of a deal for Kelly Olynyk and Ochai Agbaji, a 2024 first-round pick that became Ja'Kobe Walter, and a 2026 first-round pick that they shipped out to acquire Brandon Ingram long before it was used to select Keaton Wagler.

Sure, the benefit of hindsight makes this look worse. But it didn't look great in real-time, either. Toronto definitely would have held more leverage moving Siakam over the 2023 offseason or sooner, when interested parties would've gotten at least one full season's worth of his services before needing to pay him.

Atlanta Hawks: Trae Young (January 2026)

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Trae Young's exit from the Atlanta Hawks was an incredibly slow burn. Speculation about his future in Atlanta began no later than 2023, amid reported questions about the team's direction and his long-term fit.

To the Hawks' credit, there never seemed to be a clear suitor ready to fork over a Godfather package for Young. People mused about the Orlando Magic and San Antonio Spurs for years. It never came across as anything more than a thought exercise among armchair general managers, though.

Still, while Atlanta held out hope for a larger trade return or a core headlined by Young that could win, his trade value appeared to deteriorate.

He missed extensive time in two of the past three seasons. He shot 34 percent or worse from distance in three of the last four years. And most notably, the appetite for building around small, highly paid ball-dominant guards evaporated.

Atlanta wound up waiting so long that it moved Young at the absolute nadir of his value...and while he was injured. The return it received—CJ McCollum's expiring deal and Corey Kispert—amounted to little more than a salary dump.

Whatever your prior thoughts on Young, the Hawks surely could have gotten more for him had they acted during the 2025 offseason, if not even sooner.

Milwaukee Bucks: Giannis Antetokounmpo (June 2026)

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You can point to numerous occasions over the years when the Milwaukee Bucks could have moved Giannis Antetokounmpo. Fortunately for them, waiting too long didn't obliterate their return.

Milwaukee landed Tyler Herro, Kel'el Ware, Jaime Jaquez Jr., Kasparas Jakučionis, the No. 13 pick in the 2026 draft (Nate Ament), two additional first-rounders, a first-round swap and a second-round pick from the Miami Heat in exchange for their two-time MVP. The Bucks couldn't have hoped for much more if they jettisoned him in 2023 (when they instead acquired Damian Lillard), 2024 or 2025.

Of all the missed opportunities, though, the 2025 offseason looms largest.

The Bucks waived and stretched Lillard to facilitate Myles Turner's arrival on a four-year, $108.9 million deal. It was an extremely desperate move presumably made in hopes it would help retain Giannis for more than one additional season.

So much for that.

Not only did Giannis soft-launch a trade request that offseason anyway, but he also was up for grabs leading into February's trade deadline. After the Bucks failed to move him then, things turned contentious in more ways than one, culminating with Antetokounmpo openly calling out the organization for sidelining him despite his wanting to play.

Never mind the dramatics, though. Or the prospect of extracting more value out of his new team. The Bucks could have avoided putting $22.5 million in dead money on their books for the next half-decade if they acted earlier—or, rather, when they should have.

Memphis Grizzlies: Ja Morant (June 2026)

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Ja Morant's trade value began a steady-then-meteoric decline almost immediately after he won Most Improved Player, made his only All-NBA team and finished seventh in MVP voting to close out the 2021-22 campaign.

This isn't to say the Memphis Grizzlies should have possessed the foresight to move him then. He was among the most electrifying and untouchable players at the time. But they ignored plenty of signals in the aftermath of what was supposed to be a franchise-altering campaign.

There were off-court issues that resulted in two suspensions during the 2023 calendar year. There was the year-over-year descent of his rim frequency. And of course, there was the growing list of absences.

Morant left Memphis having missed 20-plus games in each of the past five seasons, including an average of 55-plus tilts since 2023-24. While the inclination to rehabilitate his value is understandable, the endeavor lasted too long. Frankly, it imploded the moment that the Grizzlies dealt Desmond Bane to the Orlando Magic last summer.

It isn't clear when Memphis would've needed to move Morant to ensure it received more than what it ultimately accepted (Jerami Grant and Kris Murray). But there were enough indications for years that this union was heading down the wrong path.

Acting sooner may have helped the return and spared the franchise an extended period of spinning its wheels.

Boston Celtics: Jaylen Brown (July 2026)

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Viewed through the lens of the 2025-26 season, the Boston Celtics traded Jaylen Brown at the peak of his value. He averaged a career-high 28.7 points per game, finished sixth in MVP voting and made second-team All-NBA.

Looking at the Celtics' return for Brown tells a different story. They received what will top out as two first-round picks, two second-round picks and 36-year-old Paul George, a capable player who is nevertheless on one of the league's worst contracts.

The fundamental question: Could Boston have gotten more if they shipped Brown out sooner? Whatever answer you give is debatable.

More went into moving Brown this offseason than the Celtics' open pursuit of Giannis Antetokounmpo. Whether analytical, financial, logistical or emotional, the dynamics that nudged him out of Beantown didn't materialize out of nowhere. Boston had enough information to make the call earlier.

"Earlier" doesn't refer to an undefined timeline, either. The Celtics entered cost-cutting mode last summer on the heels of Jayson Tatum's Achilles injury and should have acted on Brown's future then.

Yes, moving him in 2025 would have bilked Boston of a 56-win campaign. But when that collective effort ended in a first-round collapse, who cares?

Increasing their first-round pick's value in the final year before lottery reform and ahead of a loaded top of the draft would have jibed with the bigger-picture financial concerns team president Brad Stevens claims the Celtics had about the current core.

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Dan Favale is a National NBA Writer for Bleacher Report. Follow him on Bluesky (@danfavale), and subscribe to the Hardwood Knocks podcast, co-hosted by Bleacher Report's Grant Hughes.