July 1, 2023 was a day fans of the Portland Trail Blazers dreaded, but knew it was inevitable.
After 11 years with the Blazers, franchise star Damian Lillard requested a trade away from the organization.
The news sent intense shockwaves through the NBA. Lillard, one of the most loyal and dedicated players in the association, has spent his entire illustrious career with the Blazers — giving his all to the team, city and fans.
Lillard’s time with the Blazers has been nothing less than historic. He was named the 2012-13 NBA Rookie of the Year, earned seven All-NBA selections, seven All-Star selections, was named to the NBA’s 75th Anniversary Team and became the Trail Blazers’ all-time scoring leader.
On top of this, Lillard wrapped up one of his most impressive individual seasons, averaging 32.2 points, 4.8 rebounds and 7.3 assists per game — with a historic 71-point performance.
Despite making it abundantly clear that Portland is the place Lillard wants to spend his whole career, the Blazers’ front office forced the seven-time All-Star to request a trade.
For the last several seasons, the team has struggled to build a title-contending roster with Lillard. From the regimes of Neil Olshey to Joe Cronin, the front office failed at delivering a competent roster able to compete outside of the first round, or even make the playoffs.
Ownership played a substantial role in the team’s inability to craft a title-contending roster. In a league where superstars dictate the landscape of the league, investing in quality talent is essential. It has been a trend throughout Lillard’s tenure with the organization for the team’s reluctance to spend money.
After a disappointing 2022-23 season, fans looked towards the off-season for the team to use their draft capital and young assets to acquire an All-Star-caliber player. Instead, the organization made it clear that their intentions are to go younger — as Lillard wants to play with veterans and compete for a championship. This was seen when the front office opted to draft the promising young prospect Scoot Henderson with the third pick in the 2023 NBA Draft instead of finding a trade package that could land them a key contributor.
Over the last several years, the Blazers have failed to land any major free-agent names. In an effort to be transparent, yes, Portland is not a big free-agent destination, but it feels as if the organization in the last decade has refused to use money as leverage to land these top free agents.
Unfortunately, ownership has been hesitant to make significant financial commitments or sacrifices, leading to a roster that lacks depth and star power alongside Lillard.
Another prominent misstep by the front office was the failure to recognize the ceiling of the Lillard-CJ McCollum backcourt.
McCollum was a key contributor alongside Lillard, averaging 19.0 points, 3.4 rebounds and 3.4 assists per game across nine seasons in Rip City.
While both players during their time together were undoubtedly one of the best backcourts in a guard-heavy Western Conference, their scoring production wasn’t enough to put them over the top as championship contenders. The Lillard-McCollum era was lackluster on the defensive end. With Lillard and McCollum not being the best defensive backcourt — paired with former head coach Terry Stotts’ defensive schemes — the Blazers were mediocre on defense in recent years.
The Blazers have been a bottom-five team in defensive rating for the last four seasons — with the team being ranked No. 29 in their 2020-21 and 2021-22 campaign.
Though the Western Conference Finals run that saw the Blazers get swept by the Golden State Warriors in 2019 instilled hope in the pairing of Lillard and McCollum, it was clear that the team was in desperate need of defense — specifically a defensive wing. Despite the request from fans and analysts to explore alternative pairings with Lillard, the Blazers remained steadfast in their commitment to this backcourt for far too long. The front office continued with horrible contacts and questionable trades that left the team hovering at the same spot with no improvement.
The Trail Blazers have run into a number of unfavorable deals that have restricted its ability to make the necessary roster upgrades.
Even when the Blazers decided to split up Lillard and McCollum, they did not receive any valuable pieces that could help them contend aside from Josh Hart — who they ended up trading the very next season.
In 2022, when the Blazers moved guard Norman Powell — who averaged 18.0 points, 3.3 rebounds and 2.0 assists with the team — the organization traded him for Eric Bledsoe, Justise Winslow, Keon Johnson and a 2025 second-round draft pick — assets that could not help Lillard compete.
By far one of the most questionable moves during Lillard’s tenure with the Blazers was re-signing guard Allen Crabbe in 2016 to a four-year, $75 million contract. Crabbe was a valuable role player but was not worth a contract of a second- or third-option player. Crabbe went on to average 10.7 points and got traded to the Brooklyn Nets in 2017.
These trades and contracts did not help Lillard compete among the top teams in the conference and limited the team’s financial flexibility.
The expected departure of Lillard should serve as a wake-up call for the Trail Blazers front office and ownership. The Blazers were handed gold, selecting Lillard with the sixth overall pick in the 2012 NBA Draft after their last high-profile draft prospects — Brandon Roy and Greg Oden — had their careers ended early due to injury.
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The Blazers must realize that they failed one of the best guards to ever play in the NBA by not providing him with the necessary tools to succeed.
It is crucial that the Blazers learn from their mistakes and avoid making similar blunders with their promising young talents in Anfernee Simons, Shaedon Sharpe and Henderson. These young players deserve a front office that is committed to building a championship-caliber team around them. The Blazers must invest wisely, spend when necessary and make prudent decisions to ensure a brighter future once they enter the post-Lillard era.
As for Lillard, the Trail Blazers failed him — it is unfortunate he will be forever used as a blueprint for franchises of what not to do with a generational talent.
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