Ranking the Portland Trail Blazers’ 4 best offseason moves

The Portland Trail Blazers have been one of the most discussed teams throughout this NBA offseason. There was a lot of buzz around Damian Lillard’s desire to add veteran help, followed by his trade request. As a result of the trade request, Portland is now expected to shift gears and transition into a rebuilding phase.

Even before this rollercoaster offseason, the Blazers had two young players, Shaedon Sharpe and Anfernee Simons, who showed great promise. This summer, they’ve done an excellent job adding to that young core, mainly through the draft.

Here are the top four best moves the Blazers’ front office has made this offseason to start this new era.

Blazers’ best offseason move No. 4: Drafting Rayan Rupert at pick No. 43

Rayan Rupert was one of the youngest players in the 2023 NBA draft class at 19 years old. He played professionally overseas for five years, most recently for the New Zealand Breakers. Last season with the Breakers, Rupert averaged 6.6 points, 2.5 rebounds, 1.0 assists and 0.8 steals on 36/25/70 shooting splits in 19.7 minutes per game.

Rupert is 6-foot-6 with a 7-foot-3 wingspan, which means he has the physical traits and the potential to be a great defender who can guard multiple positions.

Amongst wings, Rupert had the second-longest wingspan in the draft class, behind only the Indiana Pacers’ Jarace Walker. For context, All-Defensive First Team forward Mikal Bridges has a 7-foot-1 wingspan.

Bridges could be a good comparison in terms of defensive upside. However, Rupert must bulk up to become a lockdown wing. He’s currently listed at 185 pounds, while Bridges is 209 pounds.

Given his combination of length, agility and quick hands, Rupert can guard ball handlers and wings. Portland has been missing his kind of defensive upside and versatility, particularly in its young core.

While he could be a better shooter, Rupert can contribute offensively by utilizing his length and athleticism. Portland’s plethora of athletic guards will be entertaining to watch run in transition with Rupert, although he might shrink the floor early in his career as teams dare him to shoot.

However, as one of the youngest players in the draft class, Rupert still has plenty of time to develop his shooting. Portland isn’t in win-now mode anyway, following the seemingly inevitable Lillard trade. They didn’t know that when selecting Rupert, but in retrospect, the pick makes even more sense.

Heading into the draft, Rupert was projected in many mock drafts as a late-first or early second-round pick. In ESPN’s draft projections, Rupert was the No. 17 overall prospect and referred to as a “potential lottery pick.”

The Blazers made a great selection, taking a flyer on a developmental project at No. 43. The value and upside certainly outweigh the risk associated with the draft capital spent.

Blazers’ best offseason move No. 3: Drafting Kris Murray at pick No. 23

The Blazers might have sniped the Kings in the 2023 NBA Draft. Sacramento had pick No. 24 and could’ve targeted Kris to pair with his twin brother, Keegan Murray.

Whether or not that was the case, it was a solid pick for the Blazers.

At the time, they were also in talks of trying to accumulate veterans to help them win now in an attempt to keep Lillard content. That might have factored into the Blazers’ decision to select Murray, a 22-year-old Junior, out of the University of Iowa.

Murray is coming off a Third-team All-American and First-team All-Big Ten season in which he averaged 20.2 points, 8.9 rebounds, 2.0 assists, 1.2 blocks and 1.0 steals per game on 48/34/73 shooting splits. Lillard reportedly didn’t want to play with rookies, but at least this is a rookie who is ready to contribute immediately.

This pick was perfect at threading the needle and maintaining flexibility – although Lillard ultimately still requested a trade, Murray is a great player to have to help catalyze the rebuilding process, too. He’s exactly what the team needs as a two-way forward, as evidenced by his 1.4 steals per game in NBA Summer League action. The Blazers needed wings, size and defense, and Murray checks all the boxes.

Murray’s other stats in his five summer league games were 10.0 points, 4.4 rebounds and 1.2 assists on 43/32/57 shooting splits in 24.7 minutes per game. Admittedly, his summer league wasn’t as great as some had expected. If he wants to become a starter at the NBA level, Murray must become an above-average 3-point shooter. Shooting 32 percent from three isn’t efficient enough to keep the defenses honest, as they will sag off and clog driving lanes.

Even if Murray is only an average shooter entering his rookie season, he can impact winning. He will likely not be a home-run pick; still, Murray can be the role player every team needs. He’s a pick that fits a positional need and will help shape a young core’s identity as a two-way player.

Blazers’ best offseason move No. 2: Re-signing Matisse Thybulle

Speaking of great wing defenders, the Blazers retained Matisse Thybulle, who already has two All-Defensive Second Team awards on his resume. As a restricted free agent, Thybulle signed a three-year, $33 million offer sheet with the Dallas Mavericks, which Portland decided to match. It was a reasonable contract that made sense for the Blazers to match.

At 26, Thybulle is just entering his prime. Portland acquired Thybulle from the Philadelphia 76ers as part of last season’s trade deadline deal involving Josh Hart. Following the trade deadline, Thybulle nearly doubled his production in every statistical category, mainly due to his increased opportunity in Portland.

In the 22 games he played as a Blazer last season, Thybulle averaged 7.4 points, 3.5 rebounds, 1.4 assists and 1.7 steals on 44/39/63 shooting splits. The shooting from deep was a bit of an outlier, as Thybulle is a career 33 percent 3-point shooter.

Despite some offensive limitations, Thybulle is another piece of the puzzle who meshes well with the Blazers’ core. Since their promising core of Henderson, Sharpe and Anfernee Simons are all guards, Portland needed to retain a two-way wing like Thybulle.

He gives head coach Chauncey Billups another element to his roster construction. Because of this signing, Billups now has the flexibility to either start Sharpe at small forward or bring one of the young guards off the bench in a sixth-man role and keep Thybulle as the starter.

Similarly to what made Murray a good fit, Thybulle fills a positional need as a defensive-minded wing. He’s a great complementary piece alongside the trio of guards as someone who can impact winning without needing to score.

Blazers’ best offseason move: Drafting Scoot Henderson at pick No. 3

Selecting Scoot third overall seemed close to a no-brainer, as many analysts had a clear-cut top three draft prospects in Victor Wembanyama, Brandon Miller and Henderson. The more difficult decision for the Blazers front office was what to do with the pick itself and whether they should keep it or trade it to get veteran help to surround Lillard.

Selecting Henderson comes in as the Blazers’ best offseason decision, not just because Henderson himself is an excellent pick, but also because they didn’t end up trading it.

In the long run, the Blazers’ most realistic chance at winning another championship was the rebuilding route, especially if there wasn’t an available trade for a superstar that would’ve genuinely moved the needle to make Portland a championship contender.

Henderson only played one game in the NBA Summer League, but he showcased some of the potential that makes him such an intriguing player. In only 21.3 minutes, Henderson scored 15 points and added 6 assists, 5 rebounds, 1 steal and 2 turnovers on 39/33/100 shooting splits.

Had Henderson played more, he would’ve been close to recording a triple-double in his first NBA action. He is already great at utilizing his athleticism to impact the game, including rebounding as a guard – another reason why one of his NBA player comparisons is Russell Westbrook.

The next step in the evolution of his game will be becoming a more efficient shooter, particularly from deep. However, it’s easy to see how Henderson’s game will translate to the NBA on day one. His G League experience, athletic build, and skill set have prepared him to make an immediate impact.

Henderson has set lofty expectations for himself in his rookie season, going on the record to say that he will win Rookie of the Year. Even if he doesn’t win Rookie of the Year, Blazers fans should be excited about the team’s future outlook with the promising all-star-level potential of Henderson.