Few people in Portland want to write, “It may be time to trade Damian Lillard.” Even fewer people want to say those words out loud.
But that time may have arrived; it may be time to trade Damian Lillard. Not for Portland’s benefit; they have benefited quite a lot from Mr. Lillard both on and off the court. This trade should only take place if it genuinely helps Mr. Lillard and he agrees to it.
This isn’t the first time the city of Portland had to wonder if it was time to trade their beloved superstar when the clock on their career began approaching midnight, and the supporting cast was not doing a great job of keeping them.
February 8th, 1995 was nearly three years removed from the Portland Trail Blazers’ most recent NBA Finals appearance, and it was the last time Clyde Drexler would be seen in a Blazers uniform. He was 32 years old then and would turn 33 that year.
Lillard is 32 now and will turn 33 this summer. Modern athletic equipment and training methods allow players to perform at 32 like they are 25, but eventually, age and time catch up with everyone. Lillard, at 32, is arguably younger than Drexler was at 32, but there is still no denying he is getting older, and the end of his career is getting closer with each passing season.
Portland was a legitimate title contender in the early 1990s, going to the Western Conference Finals for three consecutive years and advancing to the NBA Finals twice. They had one of the best all-around players in the league in Drexler and a very good supporting cast. Drexler was drafted in 1983, Jerome Kersey in 1984, and Terry Porter in 1985. Kevin Duckworth was traded for in 1986, Buck Williams was traded for in 1989, and Cliff Robinson was drafted in 1989. That was an all-star roster, and new head coach Rick Adelman helped them take the league by storm in 1990, advancing to just their second NBA Finals in team history and the first since 1977. They would get to the conference finals the following year and would return to the NBA Finals in 1992, and they have not made it back since.
Drexler knew what it was like to be on the same level as the elite teams in the league, and he knew they were better than most of those teams. You don’t get to the conference finals three years in a row and make the NBA Finals twice in a span of three seasons if your team isn’t a legitimate world-beater. Drexler knew his team could beat any team on any night on any court in any city; that’s not a feeling Lillard has known during his career.
Lillard is regarded as one of the best players in the league, but he has never been on a team that anyone would confuse with being on even footing with the elite teams in the league. And he definitely hasn’t known what it feels like to know your team is better than most of the elite teams.
The 1990s Trail Blazers were tough and deep, and they knew how to win against even the best competition. The last several years of the Trail Blazers have been entertaining, but that’s about it. They aren’t tough, they don’t have a lot of depth, and they don’t get many wins in the playoffs. Teams know they can focus on Lillard, and the rest of the roster won’t be able to keep up. In the one conference finals appearance of Lillard’s career, they were swept and have not made it past the first round since.
Portland finished their 2022-23 season with the 26th worst record in the NBA, missed the playoffs for the second consecutive season, and will be in the draft lottery next month. They won’t know where they draft until the lottery teams are announced on May 16th, but they know they will have a top 10 pick at the very least as they are currently in the 5th spot in the draft based on the record and by rule cannot fall more than four spots. They will have their own pick in the first round and a first-round pick from the Knicks, which will be in the last ten picks based on New York’s record.
Those picks, along with a trade package for Lillard from another team, could be what they need to build a new roster around Anfernee Simons, Shaedon Sharpe, and Jerami Grant. Or those picks packaged together could lure a couple of players here via trade.
Portland GM Joe Cronin has stated that they are building towards a championship, but they haven’t been clear about what kind of timeline they are working with. Lillard has voiced that he needs veteran help rather than waiting for young players to develop, so unless the Trail Blazers’ front office intends to make big moves this summer, this team isn’t going to be ready to compete until around the time Lillard turns 35 and may have to rely on another star to be the leader on the court if his body struggles with the grind of professional basketball at that age.
Something Portland and Lillard need to consider is that adding star players doesn’t always result in a championship. Franchises LeBron James has played for have had good luck forming teams that way and launching themselves into title contention, but most of the league has been unable to buy themselves a title.
The Trail Blazers infamously passed on Kevin Durant in the 2007 draft, and Durant instead went to Seattle (now Oklahoma City). Many folks have wondered what it would be like if Durant landed here and automatically assumed it would have meant at least one title in Portland. But those same people need to be reminded that (a) nothing is for certain and (b) if Durant was drafted in 2007, Portland likely doesn’t have the draft capital needed to select Lillard in 2012. Careful of what you wish for.
Instead of being teamed with LaMarcus Aldridge and Brandon Roy, Durant was teamed with Russell Westbrook and James Harden. They quickly became a title contender, making the NBA Finals in 2012. Durant never won a title in OKC, but he did appear in one NBA Finals and a couple of conference finals before leaving. He signed with Golden State in 2016, where he teamed up with Steph Curry, Klay Thompson, and Draymond Green. He won consecutive titles and had a chance at a third before an Achilles injury sidelined him. He then went to Brooklyn, where he was reunited with Harden and later teamed up with Kyrie Irving. The superstars were not able to get past the second round. Durant was traded to Phoenix in February, where he will team up with Chris Paul, Devin Booker, and DeAndre Ayton. We will have to wait and see if his newest team gets him back to the game’s biggest stage.
Golden State won two titles with Durant and another two without him. Their core of Curry, Thompson, and Green was drafted and developed there. While they have been associated with forming super teams, they actually built their team much the same way Drexler’s Blazers were made and continue to be the team to which other franchises are measured in today’s NBA. Golden State went the organic route, winning a title in 2015, and only took a detour toward a super team after Cleveland formed one with LeBron James and defeated them in 2016. Once they added Durant, they beat Cleveland in the Finals in consecutive seasons. After Durant left, Curry and Thompson dealt with major injuries but made it back to the Finals in 2022, won another championship, and have a chance for another one this year.
Harden had a stop in Philadelphia alongside Joel Embiid, but they never made the NBA Finals. Westbrook was teamed with Paul George in OKC, but they never made the NBA Finals. Chris Paul was teamed with DeAndre Jordan and Blake Griffin with the Clippers but never made the NBA Finals. Paul was traded to Houston, where he would team up with Harden, but they never got past the conference finals. Paul was then traded to OKC in exchange for Westbrook, and neither team made it to the NBA Finals. Paul was traded to Phoenix to team up with Ayton and Booker, and they made it to the NBA Finals but lost to Milwaukee. They will add Durant to their lineup and see if they can make it back and win it all this time.
The Lakers signed LeBron James, traded for Anthony Davis, and won a championship in 2020. They struggled to get back to the playoffs, so they traded for Russell Westbrook, but that trio also struggled. Westbrook was traded to Utah, who released him. He signed with the LA Clippers, where he will reunite with Paul George, who was traded to LA to team up with Kawhi Leonard. George and Leonard got the Clippers to the conference finals in 2021 but have not yet advanced to the NBA Finals.
It is not always superstars teaming up; there are recent examples of star players teaming up to chase a championship. Minnesota traded for center Rudy Gobert to pair with forward Karl-Anthony Towns. We’ll see what they can do in the playoffs, but they finished as the 8th seed in the West this year. Dallas traded for Kyrie Irving to pair with Luka Doncic; they finished as the 11th seed in the West and missed the playoffs. Last season New Orleans traded for CJ McCollum to pair with Zion Williamson and Brandon Ingram. They lost in the first round last year and did not qualify for the playoffs this season.
The moral of this story is that it costs a lot of assets to get these players moved to your team, and there is no guarantee at all that it will lead to a better result than the team is already getting. Lillard deserves to play alongside another superstar, and if he wants to do that in Portland, they should make the moves necessary to make that happen. They have a roster that can’t compete for a championship, and they know that. But they have a superstar who is the face of their franchise that they need to take care of, and they know that also. Lillard is fiercely loyal, an honorable trait in a human being. He deserves to have his loyalty and play on the court rewarded with an improved roster and to know what it feels like to play in an NBA Finals game.
Clyde Drexler won a championship in Houston after losing two NBA Finals with Portland. I’m sure that title would have felt better if it had been won here, but at least he knew how it felt to lead his team to the biggest stage in the NBA, and Lillard deserves to know what that feels like as well. If he can find out what it’s like to play in the NBA Finals for Portland, that would be ideal. Still, suppose Cronin doesn’t think he has the assets to make Lillard’s supporting cast championship-worthy. In that case, he should be honest with Lillard about that and let him decide where he wants to play, provided they have the appropriate trade compensation for one of the best point guards in the NBA with a few years left in his prime.
