The Portland Trail Blazers certainly grabbed their share of the spotlight this summer, although not necessarily for the best reasons. Much of the buzz surrounding the team stemmed from Damian Lillard’s trade request after spending his entire 11-year NBA career up to this point in Portland.
Portland made a few blunders this offseason, some of which went under the radar because the main offseason focus was the Lillard news. These decisions could negatively affect the Blazers’ long-term outlook as they begin rebuilding following the seemingly inevitable Lillard trade.
But there have been other big missteps in this up-and-down offseason.
Worst offseason move No. 4: Losing Drew Eubanks
Drew Eubanks signed a two-year, $5 million deal with the Phoenix Suns this offseason. He was an underrated free-agency signing for the Suns.
In the 2021 NBA Finals, Phoenix’s lack of front-court depth was apparent and significantly affected their series loss to Giannis Antetokounmpo and the Milwaukee Bucks. Eubanks should help fix that, but now the need for a backup rim protector is evident for the Blazers.
Last season, Eubanks averaged 6.6 points, 5.4 rebounds, 1.3 assists, and 1.3 blocks in only 20.3 minutes per game. Eubanks was an excellent fit for the Blazers as a backup center with great intangibles. He was an unselfish two-way player who contributed to winning in aspects outside of scoring, including his hustle, rebounding, passing, and rim protection.
Portland’s inability to retain Eubanks in free agency on what seems to be a team-friendly contract for the Suns comes in at No. 4 for the Blazers’ worst offseason moves. Because of his age at 26 and relatively cheap contract, Eubanks would have been an ideal complementary piece for the Blazers’ retool.
Another factor that makes it worse for Blazers fans is that Eubanks is a hometown favorite who grew up in Troutdale and played his college ball at Oregon State University.

Worst offseason move No. 3: Waiving Trendon Watford
After being waived, Trendon Watford ended up signing with the Brooklyn Nets. This decision to waive Watford was a complete head-scratcher. Regardless of whether Lillard wanted to stay in Portland, keeping Watford seemed like an inevitable move the Blazers would make this offseason.
In only his second year in the NBA, Watford averaged 7.4 points, 3.8 rebounds, and 2.1 assists for the Blazers in 19.1 minutes per game. Given Portland’s porous season, emerging talents like Watford, who was undrafted in the 2021 NBA Draft, was one of the highlights.
The 6-foot-8 Watford is an ideal modern-day forward who can handle the ball, find the open man, stretch the floor, and switch in pick-and-roll situations. He was the opposite of Nurkic and gave the Blazers another dimension as a change of pace coming off the bench. As a relatively cheap contract, he fit the Blazers’ roster exceptionally well in many aspects, including timeline, position, versatility, and financial situation.
From a positional standpoint, the Blazers’ most significant roster weakness is their forwards. Why not keep Watford and have him develop with the young core, if only as a depth piece? Now that Eubanks and Watford are both elsewhere, Portland is extremely thin at their big positions. Fans are left wondering why the Blazers didn’t include the 22-year-old Watford in their rebuilding plan.

Worst offseason move No. 2: Signing Jerami Grant to a massive contract
Portland signed Jerami Grant to a massive five-year, $160 million contract this offseason. In year five of the deal, Grant will be 34 and has a player option for $36 million. He will be a negative asset in the later years when Portland’s young, promising players are just entering their prime.
The Blazers offered Grant the contract before Damian Lillard officially requested a trade. The goal with the Grant signing was to prove to Lillard that the Blazers were dedicated to building around him with veteran pieces. The plan did not work, as Lillard still requested a trade. As a result, signing Grant to such a significant contract is a mistake.
The Blazers are now in retooling mode following the selection of Scoot Henderson at No. 3 overall in this year’s NBA Draft and the emergence of Shaedon Sharpe. Grant is a great player and will likely be the Blazers’ best player this season. However, he doesn’t fit Portand’s timeline following the Lillard news. To make matters worse, he could be difficult to trade for draft picks or young assets because of the size of the contract.
From an on-court standpoint, one concern regarding Grant will be whether or not he can maintain his shooting from last season. Last year, Grant averaged 20.5 points, 4.5 rebounds, and 2.4 assists on 48/40/81 shooting splits. However, his shooting was an outlier, as he has only been an above-average shooter at 36 percent from three in his career. The contract could be even worse if Grant doesn’t maintain his elite floor spacing from last season.

Blazers worst offseason move: Overall handling of the Damian Lillard situation
The Blazers worst offseason moves listed above, particularly waiving Trendon Watford and signing Jerami Grant, made more sense if the Blazers were indeed set on building a contender around Lillard. Instead, the Blazers did exactly what they’ve repeatedly done in the past – trying to toe the line between two roster timelines. They drafted Scoot Henderson at pick No. 3 and signed Jerami Grant to a massive contract.
The decision to keep the pick and select Henderson to rebuild was likely the right move and the Blazers’ most realistic path to winning another championship. The knock on Cronin’s handling of the Lillard situation isn’t Portland’s ultimate decision to rebuild – it’s that they were so adamant that they were going all in with their chips and willing to trade young assets to get there.
This is what Joe Cronin said at the trade deadline.
— Aaron J. Fentress (@AaronJFentress) July 2, 2023
He did not follow through. And maybe for good reason. Moving forward with young talent is not a bad move.
However, that does ZERO for Lillard. He was 100% in the right to ask out.
Now, send him to his choice destination. pic.twitter.com/FRahbVDWsm
“We’re going to be ridiculously aggressive… we feel extremely obligated to put a great roster around Damian Lillard… we’ve had many conversations about how important it is for us to do right by Damian, and we plan to do that.”
Had they decided to go the rebuilding route earlier, it would have been more manageable and factored into previous moves. It was the underlying issue that contributed to the other Blazers’ worst moves this offseason.
Not only that, but it did Damian Lillard wrong by repeatedly going on record to say that the team would get him help. Lillard has been so loyal to the Blazers’ franchise when many other superstars would’ve left a long time ago and is arguably their best player of all time. He deserved more transparency throughout this entire process.

