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Trail Blazers' 3 Biggest disappointments, 3 Most pleasant surprises of 2023-24 season

It was a down season, but Portland had a few ups, too.
Andrew Hanlon
Andrew Hanlon

Rip City Project

Shaedon Sharpe, Portland Trail Blazers / Alika Jenner/GettyImages

The Portland Trail Blazers won 21 games this season. That would qualify as a disappointment. But that means the third (or fourth) best odds at landing the No. 1 pick in the 2024 draft. That's a pleasant consequence.

Deandre Ayton missed a game because he couldn't get out of his driveway in an ice storm. Disappointing. He had five 30-point double-doubles in the final month of the season. Delightful.

That's the way the season went for Portland. There were some downs followed by some ups followed by some more downs followed by some more ups. Here are the most severe disappointments and the most enjoyable developments of the year for Rip City.

Trail Blazers' 3 most pleasant surprises this season

The Dalano Banton trade

Portland General Manager Joe Cronin had some options at February's trade deadline. There were some veterans ripe for contenders' picking, including Malcolm Brogdon, Jerami Grant and Matisse Thybulle. Cronin could have added to the Blazers' asset cupboard by dealing any or all of them for future draft picks or young players.

Instead, he held onto everyone and made one seemingly insignificant move, taking Dalano Banton off Boston's hands in exchange for a future top-55 protected second-round pick.

Banton arrived in Portland as a player with tantalizing physical attributes, but one who had yet to carve out a role in the NBA. He ended the season as a potential piece of the franchise's future after averaging 16.7 points, 4.8 rebounds and 3.6 assists in 29.2 minutes across 30 games.

Is the 24-year-old's sudden rise legitimate or is he simply a product of unlimited opportunities and no consequences on a tanking team? It will only cost the Blazers a $2.2 million team option to find out, which seems worth the risk.

Jabari Walker's season-ending explosion

Jabari Walker showed some promise as a rookie in 2022-23. He flashed a high-energy game with a pinch of playmaking and a penchant for carving out space on the offensive glass. Then he added some muscle during the offseason, took advantage of the injury plague that swept through Portland's locker room this year and now finds himself on this list as one of the Blazers' biggest surprises.

The Colorado product doubled his minutes and upped his stats across the board. He finished the season averaging 8.9 points and 7.1 rebounds while shooting 46 percent from the field despite taking twice as many shots as he did as a rookie.

In his final 15 games, eight of which were starts, Walker nearly averaged a double-double and added a new wrinkle that will be critical to his development - a 3-point shot. The 21-year-old hit 39.4 percent of his 2.2 attempts per game. He also pulled down 14 rebounds per game in the Blazers' final six, including 22 in a win over the Charlotte Hornets.

Scoot Henderson's home stretch

Portland's rookie point guard also finds himself in another category on this list, but like Walker, Scoot had a strong finish to the season.

Last year's third-overall pick finished his debut NBA campaign with averages of 14.0 points, 3.1 rebounds and 5.4 assists on shooting splits of 39/33/82. Considering how he started the season - barely cracking double digits in scoring, fouling out twice, missing nine games with an ankle injury and shooting 25 percent from three before Christmas - those final numbers don't look too shabby.

But Henderson got increasingly better once the calendar turned to 2024 and had a strong final 15 games of his own. Scoot scored 18.3 points per game while dishing out 7.5 assists. He added 1.4 steals and shot 42 percent from the floor and 39 percent from three.

There's plenty of room for growth after an up-and-down season, but there's also plenty of momentum heading into a critical summer for Henderson and the Blazers.

Trail Blazers' 3 biggest disappointments this season

Injuries

Portland's No. 1 issue in '23-24 was the health - or lack thereof - of its most important players.

The Blazers were deep at the guard spot heading into the season with Henderson, Sharpe, Anfernee Simons and Malcolm Brogdon. Ayton and Robert Williams III formed a promising center pairing. Jerami Grant, perhaps the team's most versatile offensive player, was returning after signing a $160 million contract.

Scoot, Ayton, Grant, Simons and Brogdon all missed at least 20 games. Williams only played six. After a strong start, Sharpe had surgery and missed the final three months of the year.

Could the Blazers have been fighting for a play-in spot if everyone had been healthy? It's not out of the realm of possibility. But it's disappointing that we'll never know.

Shaedon Sharpe's injury

Sharpe's injury stings more than any other malady the Trail Blazers had to deal with this season. His explosion at the end of '22-23 had fans, and surely the organization, excited about the leap he could make in his sophomore campaign. Sure enough, the 20-year-old was forced into a featured offensive role after Simons got hurt in the first game of the year and excelled.

Through 21 games after he replaced Ant in the starting lineup, Shaedon averaged 19.0 points, 5.6 rebounds, 3.7 assists and 1.0 steals while shooting 37 percent from three on more than six attempts per game. He averaged 4.5 free throw attempts and hit better than 82 percent of them. The jump everyone wanted from Sharpe had happened.

Then he injured a key muscle in his core. He tried to play through it but was obviously hampered. Eventually, he had surgery and never came back.

Three more months to build on an already promising second season would have done wonders for Sharpe and three more months to build chemistry with Henderson, Simons, Ayton and the rest of the Trail Blazers' future foundation would have bled right into next season. At least he's heading into the summer with a clean bill of health and the chance to make another leap in 2024-25.

(Most of) Scoot Henderson's rookie season

Yes, Henderson gradually improved. Yes, he finished the season strong. But as a whole, Scoot's rookie campaign didn't go as planned.

He was a wildly inefficient shooter, as evidenced by his 38.5 percent shooting from the field. Even more concerning is his two-point field-goal percentage: He finished fifth-worst in the entire NBA of any player who logged at least 1,000 minutes. That's extra worrisome given his ability to use his strength and explosiveness to get to the rim. If he gets there but can't finish, then what's the point?

Even his late-season surge mentioned above came with its drawbacks. In those final 15 games, he averaged nearly 5 turnovers and had a plus/minus of -12.9.

Entering the NBA at the most difficult position in basketball at just 19 years old was always going to lead to some struggles, and Henderson got better as the season went on. But in general, it was a disappointing season for who Portland hopes will be its franchise point guard.

Andrew Hanlon

Andrew Hanlon

Andrew is a Site Co-Expert for Pippen Ain't Easy. He earned a degree in Journalism from the University of Wisconsin-Oshkosh and began covering high school sports in 2014. He's covered the NBA since 2021, and his work has been featured on FanSided, SB Nation, Yahoo! Sports, Sportscasting, and GiveMeSport. He’s been in his PAE role since 2024 and previously held the Site Expert position for Rip City Project (Portland Trail Blazers). When he's not writing about, talking about, or watching sports, he can be found playing and coaching them with his five kids.