This article is part of a larger series grading Joe Cronin’s tenure across five criteria: Trades, Drafting, Free Agency, Salary Cap Management, and Culture. You can find the previous articles in this series below:
Today’s piece is the first of two parts zooming in on Cronin’s drafting.
When Cronin was promoted to GM, the Portland Trail Blazers were coming off two straight years of sending their first-round picks to the Houston Rockets in 2020 and 2021 as part of the compensation for acquiring wing Robert Covington. In the summer of 2021, then-President of Basketball Operations Neil Olshey traded a lottery-protected first to Chicago as part of a three-team trade that brought in Larry Nance Jr. from the Cleveland Cavaliers.
The most notable name in the trade was Lauri Markkenan (who went to Cleveland), while the Bulls received Derrick Jones Jr. from Portland, a second-round pick from the Cavs, and are still waiting on the first-round pick from Portland to convey. If the pick isn’t conveyed by the 2028 draft, the Bulls will automatically receive the Blazers 2028 second-round pick. We’re in Year 5 of Portland having kept their first-round pick, as Cronin has stockpiled young talent for the rebuild.
In late 2021, Olshey was fired and the team was 11-18 when Lillard was to be shut down for abdominal surgery. The Blazers had been fielding the smallest starting line up in the NBA with Lillard, McCollum, and Norman Powell all standing at 6’3”, complemented by 6’7” Covington, and 6’11’’ Jusuf Nurkic. Nance Jr, was in and out of the lineup with injuries, and the bench was held together with Anfernee Simons, Nas Little, Tony Snell, and Trendon Watford.
At the helm of this crew of “win now” mighty mice, was first time head coach Chauncey Billups. Billups’ coaching experience to that point was one season as an assistant with the LA Clippers the previous year. The only youth on the team was the promising Simons, and oft injured, yet highly athletic wing Nassir Little. The team was capped out, and focused on using valuable draft capital to bring in talented veteran role players to support Lillard. Unfortunately, they collectively had too many warts to become a contender.
As Cronin took over as acting GM, the team was going off the rails. His actions immediately signaled the Blazers were going to do a major remodel. Gone were Powell and Covington, soon followed by McCollum, Nance Jr, and Snell. Portland then did something it hadn’t done once under Neil Olshey. They decided to stop the focus on being an also-ran playoff contender, and turn their attention to adding high-level young talent to the roster. Otherwise known on Blazers Edge as, “Cue the tank gif!!”
2021-2022: B+
The Blazers finished with the sixth-best odds for the Draft Lottery and sent Lillard to represent them for the selection process. Instead of cashing in on the 40% chance of jumping into the Top 4 in a draft headlined by Chet Holmgren, Jabari Smith Jr, and Paulo Banchero, they ended up falling into the seventh draft spot. It was the highest draft pick Portland earned since drafting Dame sixth overall in 2012. While dissecting draft prospects was a hot topic, much of the scuttlebutt amongst fans and media centered around using the seventh pick as the lead asset in trying to find a star to pair with Lillard. Some reports had Portland inquiring about former Toronto Raptors defensive ace, OG Anunoby. Speculative reporting announced the price was the seventh pick, along with Josh Hart and Nas Little.
This is a key inflection point in the Cronin tenure. The Blazers would trade for Jerami Grant a few days before the draft, knowing he was a year away from free agency with a publicized desire for a big payday. One could hypothesize if a trade for Anunoby was made, the Blazers could have fielded a starting lineup for 2022-23 with him, Lillard, the newly re-signed Simons and Nurkic, and Grant.
Instead, Cronin and his team committed to using the seventh pick and dialed in on a high-flying, mysterious wing prospect, Shaedon Sharpe. Sharpe enrolled at Kentucky but sat out the entire season for various personal reasons, so the only scouting film that existed on him was his high school footage. The 6’5” guard displayed elite athleticism and boasted a seven-foot wingspan. Hall of Fame Kentucky Coach John Calipari said, “[If] this kid comes back, he’s the No. 1 draft pick. In my mind, he’s the No. 1 draft pick. How can I say I know what the No. 1 draft pick looks like? BECAUSE I’VE HAD FOUR. That’s why I can say what it looks like. He can be the No. 1 draft pick.”
Draft results: Round 1; Pick 7: Shaedon Sharpe… Round 2; Pick 57 Jabari Walker
Notables drafted after Pick 7: Dyson Daniels, Jalen Williams, Jalen Duren
Missing out on the All-Star Williams, taken 12th by OKC, hurts a bit. Duren is currently having a big impact as part of the Detroit Pistons’ resurgence, averaging 18 points and 11 rebounds on a TS of 66%. Daniels, a jumbo playmaking guard and defensive savant, would have given Portland a very different kind of guard than Sharpe.
Shaedon has been an enigma since arriving in Rip City. Some nights he looks like a future superstar. Other nights he resembles an inefficient volume shooter who struggles to impact the game in multiple ways. His dribbling skills leave a lot to be desired for a guard with his level of explosiveness, and it gets him into trouble often, as demonstrated by his negative assist-to-turnover ratio. Defensively, he’s the weakest link in the starting lineup. Even with those struggles, the team is letting Sharpe use this season as a “self-discovery” year by allowing him a superstar usage rate of 31%. The overall results have felt somewhat disappointing given the scope of the role given.
Still, the fourth-year guard is averaging a career-high of 21.8 points, 4.5 rebounds, and 2.6 assists. On the eve to the start of this season, the Blazers signed Sharpe to a four-year, $90M rookie contract extension, keeping him under the team’s control through the 2029-30 season. They have time to continue to let him show improvement, and his contract appears to be a good value. The emergence of Deni Avdija has lifted some pressure off Sharpe’s shoulders of becoming a franchise cornerstone. Expectations for who Sharpe ought to be seem to shift week to week this season. Lately it has felt as though he’s auditioning for the long-term role as the second option to Deni, rather than bursting into a superstar in the mold of Anthony Edwards or Jaylen Brown.
Shoutout to Jabari Walker who played three seasons with Portland before becoming a valued contributor during the rebuild, averaging 6.2 points and 4.5 rebounds in 16.3 minutes. His contract expired, and he was not offered a new one from Portland. He signed a two-way deal with Philadelphia last summer and is averaging 4 points and 3.5 rebounds in 13 minutes over 39 games.
To finish with Shaedon, Cronin’s gamble on the mysterious “Maple Jordan” out of Canada has been a positive part of the rebuild. Whether Sharpe can reach loftier heights remains to be seen, but he brings an unique attack that other teams must account for. It should only get seasoned and more difficult to stop with more experience. He might not become the superstar that a lot of fans have hoped for, but his floor is trending towards a valuable 2nd or 3rd option for a contender.
2022-2023: C
Note: Their draft grade could improve if Scoot brings the extra credit.
Portland’s retooled lineup raced out to a 10-4 start to the season which brought some new hope. Perhaps Billups got better? Perhaps it was proof that Dame and CJ needed to be broken up to breathe new life into the team? That fun newness wore off quickly, as the team rapidly began to fall apart. Starting Lillard and Simons together proved to be a fatalistic decision for the team’s defense. The team looked different with new players, but one thing didn’t change. The team stayed too small. Lillard began to go in and out of the lineup with calf soreness. He gave his best individual effort though and it led to a career high in scoring.
However, the system became far too dependent on Lillard. He had to score at least 35 just to give the team a chance to win each night. At the trade deadline, Josh Hart was dealt to the New York Knicks for reclamation project Cam Reddish and the Knick’s 2023 1st round pick. Hart would have been great to hang onto, but he was in need of a new contract in the offseason. After re-signing both Simons and Nurkic the previous summer, and planning to offer Grant a new contract in the upcoming summer, it made Hart a financial casualty. Bringing on the 6’8”, 23-year-old Reddish signaled that Cronin was trying to get the team younger, and felt good about calculated gambles on very talented, but flawed prospects. (see: Simons, Sharpe, Keon Johnson, and Reddish).
The veterans were shut down shortly after the trade deadline, as they were the year prior, and Portland ended up with the 5th best lotto odds. This was the ultimate draft to tank for with the greatest prospect since LeBron James at the top: 7’5” Frenchman Andre the Giant Victor Wembanyama. The Blazers sent legend Brandon Roy to the draft lottery, as the last time he went in 2007 the Blazers landed the #1 pick! Alas, Roy walked away by jumping up two spots from fifth place to bring home the third pick.
This was widely considered a Big 3 Draft with Wembanyama, wing Brandon Miller, and G League point guard Scoot Henderson headlining. With one of those three picks, the strategy question was once again raised: Should Portland use the pick to swing a blockbuster trade to help Lillard, or look to add a highly talented rookie? The pick was reportedly “shopped,” but Cronin said confidently several days before the draft that the team was planning to use the pick. Scoot Henderson landed in Portland’s lap, and it appeared they may have drafted their backcourt of the future in consecutive drafts.
Henderson had foregone college in lieu of playing in the G League for two years. He was part of a specially designed team called the Ignite, which was supposedly for the top NBA prospects to develop on. The league has since ended the program as multiple high-level prospects came into the NBA underdeveloped. Scoot’s raw numbers were modest, but what wasn’t was his rare acceleration with the ball, court vision, and aptitude for passing. Many experts labeled him a generational talent, and possibly the best point guard prospect since Kyrie Irving. Scoot and Wembanyama even squared off in a nationally televised exhibition game where Henderson shined with 28 points, 9 assists, and 5 rebounds.
Portland waited with bated breath while Adam Silver announced the Charlotte Hornets picked Brandon Miller. Yes, it happened! Portland was going to end up with the player some said would have been the number 1 overall pick in a non-Wemby draft. But, what about Dame? Simons, then Sharpe, and now his replacement in Henderson were supposed to be the answer to getting a Lillard-led team over the hump? Dame asked to be traded on the first day of free agency, and the retool officially transitioned into a rebuild.
Draft Results: R1;P3: Scoot Henderson… R1;P23: Kris Murray… R2;P43: Rayan Rupert
Notables drafted after: Amen Thompson, Keyonte George, Toumani Camara
Thompson deserves consideration as a massive whiff by Cronin, as he is an integral part of a Houston team looking to contend for a title. It should be noted that Cronin passed over two guards in back-to-back drafts that might have been immediate smoother fits next to Lillard. 6’8” Dyson Daniels and the 6’7” explosive Thompson. Both are tremendous defenders and playmakers. George has been a surprise value for the Utah Jazz after being drafted 16th. He’s averaging 24 points and 6 assists in his 3rd season. Questions remain if he’s good enough to build around. Toumani Camara would likely be a Top 10 pick in a redraft instead of the 52nd. The Suns did an excellent job drafting him.
Scoot came to Portland riding a wave of hype and sky-high expectations in trying to backfill the shoes of the team’s most iconic player. Billups gave him the ball and he started the first nine games of the 2023-24 season. To say he underwhelmed would be an understatement. The game was too fast for him to process, and while he showed he could get into the painted area rather easily, once he got there, his decision making often froze. Turnovers plagued him. His jump shot, a concern coming in, showed to be as rough as he displayed in the G League. He was benched for veteran Malcolm Brogdon, who helped buoy the team as it started over with a vastly new-looking squad.
Henderson would look better later in the season, after dealing with an early season ankle sprain. Scoot would go on to start in 32 out of 62 games played. His rookie line: 14 points, 3 rebounds, 5.4 assists on TS of 49% and 3-point shooting of 32%, with an assist-to-turnover ratio of 1.55. The hyped 3rd overall pick didn’t even gain a spot on the NBA’s first or second All-Rookie team. Ouch!
He’d come back in 2024-25 looking like he was dealing with the same struggles, but started to turn things around in January. He had a great month shooting the ball with an outlier TS of 64%. The efficiency began to dip back down until he suffered a concussion in March that ended his season. He played in 66 games, starting only 10 of them. His numbers looked better across the board as a starter, but incumbent combo guard Anfernee Simons stayed entrenched as a starter for all 70 of the games he played.
Scoot Henderson has not played in the 2025-26 season due to a hamstring tear suffered days before training camp opened. His future as a Blazer is unclear, but there are several current candidates on the roster outside of Scoot who can function as the team’s point guard. His uphill climb to gain relevance and traction in Portland continues.
Kris Murray was a safe plug-and-play pick with the 23rd selection, gained when Josh Hart was sent to the Knicks. The 6’8” forward struggles with shooting the 3, but he’s a heady player who gives great effort on defense and makes the right reads on offense. He has one season left for Portland to decide his future, but he appears quite expendable on this team.
Rayan Rupert was so highly thought of by Cronin, the team offered him a guaranteed contract as a second-round pick. The 6’6” wing with a ridiculous 7’3” wingspan looks the part of a good NBA player. He moves very smooth, has solid defensive instincts, can do a little playmaking, but lacks any semblance of consistent offense. Portland kicked the tires on him as an interesting prospect, and he’s still very young. But Rupert currently looks like an afterthought as his contract expires at season’s end.
Cronin made the choice that most GMs in his spot would have when drafting Scoot. However, after a checkered two-and-a-half years of performance and injuries, many questions remain unanswered about Henderson. Thompson meanwhile, is averaging 18.5 points, 7.7 rebounds, and 5.1 assists and is a reigning All-NBA Defense First Teamer. Scoot is going to have to return as a different player with one year left on his rookie deal for his selection at number 3 to justify itself. Amen Thompson’s progress and impact will be a ghost that chases Scoot (and Cronin’s decision) until he proves otherwise. We’re officially two and a half years in, and the Blazers don’t have a lot to show from their highest draft pick since 2007.
Keep your eyes peeled both for part 2 of Joe Cronin’s draft grades (where I’ll round out the latest two drafts and share my overall grades for Cronin during his tenure), and for my grades on Cronin’s management of Free Agency, the Salary Cap, and Culture.
