In 2021, the Portland Trail Blazers were one of the teams in the running for Orlando Magic's Aaron Gordon. Instead, they came away with Robert Covington and Norman Powell in separate deals, two players they proceeded to sell low on by trading them to the Los Angeles Clippers for pennies on the dollar (Eric Bledsoe, Justise Winslow, Keon Johnson, and a second-round pick).
Portland's draft capital was scarce after trading two first-round picks for RoCo, similar assets they used to initially offer for Gordon, who was viewed as their No. 1 target. But there was still a possibility of the Blazers being able to pair Gordon and Covington if they were willing to part ways with some of their young talent.
The Trail Blazers missed out on Aaron Gordon
Here's what Yossi Gozlan, who was writing for HoopsHype at the time, wrote on Portland's situation:
"In the absence of first-rounders, Portland can offer some of their young players such as Gary Trent Jr., Anfernee Simons, or Nassir Little as incentives. However, they may not want to part with any of these players at this moment as they are high on them."
He adds, "One other player the Magic could have interest in is Derrick Jones Jr. ($9.3 million), who would probably be the odd man out of the Trail Blazers starting lineup with Gordon in."
Gozlan does note that the Magic may be able to get more from Gordon elsewhere, but their actual trade of Gary Harris, R.J. Hampton, and a 2025 first-round draft pick wasn't far off from the Blazers' assets.
Fast forward to 2025, and it looks like both the Blazers and Magic would have been better off trading with one another. Harris and Hampton have been underwhelming, and Denver's 2025 first-round pick is projected to be the No. 25 selection. They still have yet to address their playmaking and shooting woes and, ironically, have been linked to Simons this summer.
For the Blazers, adding Gordon would have helped solve the most significant roster problems that plagued them throughout the Damian Lillard-CJ McCollum era: their lack of size and reliable wing depth. Portland had regular-season success but wasn't built to be a sustainable playoff team, and adding Powell into the mix didn't help solve any of these problems.
Additionally, the Blazers' starting lineup already had enough offense to compensate for Gordon's inconsistent shooting.
Trading for Gordon may not have been enough to firmly put Portland into contention, and it's also worth noting that Gordon is a perfect fit in Denver with a style of play that complements Nikola Jokic. Still, one NBA championship and two Gordon game-winners later, we can't help but wonder how things would have played out.
Maybe it would have been enough to keep Lillard in Rip City.