Portland Trail Blazers star point guard Damian Lillard is about as faithful as they come in the NBA. Since entering the league in 2012, Lillard has put the Blazers on his back carrying them each season. He has become the face of the franchise.

This season, he has been averaging 28.4 points, 4.2 rebounds and 7.5 assists per game, but he has been producing like this for years now.

There is more to great players than the number of championship rings on their finger. That is why no one thinks Robert Horry is the GOAT even though he has more rings than Michael Jordan. Nevertheless, the long-running narrative is that there is a blemish on a player's legacy if he does not come away with at least one championship. Lillard is well on track to being one of these players.

While the Portland front office is not terribly run, one would think that Lillard would have received more help by now. The last All-Star teammate Lillard had was LaMarcus Aldridge before he left for the San Antonio Spurs, although one can make a case that CJ McCollum has been playing like an All-Star.

The Blazers have been a good team for years, but with an amazing player in Lillard, they could have been something more. Sure, the team has good regular-season records, but they are never in conversations to win the Finals or even make it out of the Western Conference.

McCollum is beloved by fans, but if the front office traded him for a player that complemented Lillard better, then maybe Portland could have been a contender. The backcourt of Lillard and McCollum is incendiary, but they regularly get exposed in the playoffs for their lack of defense and size.

Article Continues Below
More Portland Trail Blazers News
Los Angeles Lakers forward LeBron James (23) drives to the basket during the second half against Portland Trail Blazers forward Toumani Camara (33) at Moda Center.
NBA rumors: Lakers insider drops eye-opening Blazers intel on potential trade candidateJulian Ojeda ·
Michael Porter Jr. photoshopped in Trail Blazers jersey (number 1)
Trail Blazers trade proposal for Michael Porter Jr. after postseason strugglesBailey Bassett ·
Austin Reaves (number 15) photoshopped in Trail Blazers jersey
Trail Blazers trade proposal for Austin Reaves lands Lakers a centerBailey Bassett ·
Malik Beasley playing basketball. Pistons logo in background.
Ranking 4 best Malik Beasley free-agency destinations if he leaves PistonsBailey Bassett ·
The Houston Rockets invested heavily into Fred VanVleet during the 2023 offseason. Houston gave the point guard a three-year, $128 million deal in a move that was meant to turn the Rockets from a rebuilding team into a championship contending one. The signing did just that, as the Rockets finished the 2024-25 regular season as the two-seed in a stacked Western Conference. VanVleet was the veteran presence and 3-point shooter that the team desperately needed, and he still might have a role with the Rockets going forward. Houston has a team option on his contract for next year, and they very well may pick it up. The Wichita State product reportedly wants to stay in Houston, but the point guard would be set to make over $44 million next season under his current contract. The Rockets and their guard recently pushed back the deadline on Houston's decision with VanVleet, and although reports suggest that they are interested in writing up a new, long-term deal, it isn't necessarily a guarantee that VanVleet will be playing for Houston next year. The Rockets blew him away with an offer he couldn't refuse back in 2023, and another team could so the same when/if he hits the open market this offseason. If VanVleet does become an unrestricted free agent, which teams outside of Houston would make the most sense for him to sign with? 1. Orlando Magic Jalen Suggs and Franz Wagner recently signed big deals with the Orlando Magic, and Paolo Banchero will be getting a mega contract extension here soon. Because of that, the Magic no longer have money to blow like they have had in recent years. That will make a deal for another big ticket free agent hard to pull off, especially considering the team signed Kentavious Caldwell-Pope last year. If Orlando can make the money work, though, then Fred VanVleet would be a great fit with the Magic. The Magic finished dead last in 3-point shooting this season, and VanVleet has made at least 2.5 deep balls per game in every season since 2018-19. VanVleet can hit shots form behind the arc off of the bounce or in catch-and-shoot situations. The Rockets were heavily reliant on his shooting expertise, so the guard would have plenty of familiarity getting up deep shots with high volume if he signed with the Magic. While undersized, VanVleet is a pesky defender, so he'd fit right in with a Magic team that has one of the best defensive units in the league. VanVleet could play alongside Suggs and give opposing teams fits. Ultimately, though, the Magic just need more shooting to get to the next level, and VanVleet is arguably the best shooter who could be available on the open market this offseason. 2. Brooklyn Nets A more realistic option for a VanVleet destination would be the Brooklyn Nets. The Nets are set up to have the most cap space this offseason, and they have a major need at point guard. With D'Angelo Russell and De'Anthony Melton hitting free agency this offseason, the Nets don't have a true point guard under contract for next season. Brooklyn needs to spend big this offseason, and they'd be smart to offer VanVleet a contract big enough that he'd have no choice but to leave Houston. VanVleet averaged 14.1 points per game last season, which was his lowest mark since 2018-19. He is trending the wrong way, but he still has enough left in the tank to give the Nets a few good seasons. 3. Portland Trail Blazers In the same way that the Rockets were looking to take the next step in 2023, the Portland Trail Blazers could use VanVleet's presence to get over the hump. The Trail Blazers have plenty of big man depth, as centers Deandre Ayton, Donovan Clingan, Robert Williams, and Duop Death are all under contract next season. Portland also has a lot of wing depth. Deni Advija started to look like a star late this past season, Toumani Camara is an elite defender, Shaedon Sharpe is a freakish athlete, and Jerami Grant is a proven scorer. The team is thinner in the backcourt, though. Anfernee Simons is a solid scorer, but Scoot Henderson has looked like a fringe draft bust since being drafted third overall. Portland shouldn't give up on Henderson completely, but there wouldn't be any harm in signing another guard. Like the Magic, the Blazers were one of the worst 3-point shooting teams in the NBA. VanVleet would improve that weakness, and in a stacked Western Conference, Portland needs all of the help they can get if they are to compete for a playoff spot.
Ranking 3 best Fred VanVleet free-agency destinations if he leaves RocketsBailey Bassett ·
Ranking 5 best Darius Garland trade destinations if Cavs blow it up
Ranking 5 best Darius Garland trade destinations if Cavs blow it upJulian Ojeda ·

Lillard has similarities to Golden State Warriors superstar Stephen Curry. Both did not come from a college basketball powerhouse, have similar frames, can light up the scoreboard, have tight handles, and make plays for their teammates.

Ideally, Portland finds their own version of a Klay Thompson, someone who can defend the best perimeter player on the other team, play with low usage, and be deadly from deep, especially in spot-up situations.

Speaking of personnel choices, while Portland regularly does not draft high–because of their regular-season success–they have not had a homerun selection since McCollum. Nassir Little and Anfernee Simons have shown flashes of potential, but they are just that … flashes (at  least for now, but until when?).

In the 2017 draft, they ended the night with the wrong Collins, getting Zach Collins from Gonzaga instead of John Collins from Wake Forest. The latter would have provided athleticism, scoring, and can serve as a reliable small-ball five.

Lillard has said on numerous occasions that he is not going anywhere and wants to retire as a Blazer. The organization owes it to Lillard to give him a better supporting cast and try harder to match his individual success with team success. The Dallas Mavericks were able to do it for Dirk Nowitzki; hopefully, Portland can do the same.