The Portland Trail Blazers had success during the Damian Lillard era with a record of 422-347, resulting in eight playoff appearances. Unfortunately, the regular season success didn't translate to the postseason that often. In those eight playoff seasons, the Blazers had a 22-39 postseason record, making just one Western Conference Finals in 2019 only to get swept by the Golden State Warriors.
In the playoffs, Lillard averages 26.1 points, 6.2 assists, 4.4 rebounds, and 1.2 steals on 41/37/89 shooting splits. Those are very similar numbers to his regular season career averages, so it's apparent that Lillard wasn't the problem come playoff time.
It's the same issue that led to Lillard's departure from Portland -- his lack of a supporting cast.
The Blazers' current supporting cast is exactly what Damian Lillard needed
Not only were they not talented enough to make a deep playoff run, but the overall roster construction didn't work in terms of fit. For as electrifying the Lillard-CJ McCollum backcourt was on offense, having two undersized offensive-minded guards as your two best players isn't an effective championship formula.
The Blazers finally came to that realization in 2022 when they traded McCollum to the New Orleans Pelicans, but it was too little too late at that point.
The Blazers needed to better construct a roster that compensated for Lillard's defensive weaknesses while providing complementary pieces on offense. In other words, they needed more two-way wings and rim protectors, which is exactly what they have now.
A wing rotation of Deni Avdija, Toumani Camara, and Jerami Grant would have been perfect, providing Lillard with floor spacing and defensive help with their length and switchability. Robert Williams III and Donovan Clingan would have helped protect the paint and give another dimension on defense that Jusuf Nurkic never did, while Deandre Ayton would open up the floor a bit more with his midrange shooting.
Several players currently on the Blazers' roster that would fit well with Lillard are the ones they acquired as part of the trade, either directly or through a subsequent fallout deal, including Avdija, Camara, Ayton, and Williams.
The Blazers have been playing well with Simons, a player similar to Lillard, making it clear that Lillard would have fit seamlessly with this group. Now, Portland has the tallest roster in the NBA and is much better equipped for the physicality of the playoffs. The only issue is they now have a team full of elite role players and lack a true superstar.
Could this lead to a Lillard reunion in Portland?
One can dream that Lillard eventually makes his return to Rip City with a roster that is well-equipped for his return, reminiscent of LeBron James' second stint in Cleveland to a lesser extent.
Lillard is already 34 years old and under contract for at least one more season with Milwaukee, with a player option in 2026-27. But the good news is that shooting is typically the last skillset to go for an aging player, which is encouraging for Lillard's longevity. And he's shown no signs of slowing down, as evidenced by his ninth All-Star appearance this season.
By the time Lillard is in a position to return to Portland, the Blazers' young core should be ready to make a playoff push. Lillard did previously tell Aaron Fentress of The Oregonian that he sees "there being a time" when he plays for Portland again.
With Simons set for a significant payday after next season, the Blazers could give the backcourt keys to Scoot Henderson and Shaedon Sharpe. The Bucks have an aging core and don't appear to be a true contender. Meanwhile, the Blazers have a promising up-and-coming core, making a Lillard reunion an increasingly realistic possibility.
Lillard left Rip City in hopes of landing his first championship. Ironically, perhaps the pieces the Blazers received in return for Dame will help him win his first championship -- back in Portland, where he belongs.