Last summer Kentavious Caldwell-Pope was not 100 percent sure where he would end up in free agency.
He had a player option on the final year of his contract, and it was beginning to be clear this could be his last chance to cash in on a contract and clear that the Denver Nuggets were looking to cut some payroll. He was not coming back to Denver, it appeared.
There were plenty of teams courting Caldwell-Pope too.
According to Marc Stein on The Stein Line, Caldwell-Pope knew the Dallas Mavericks were interested in acquiring him in a sign-and-trade deal. But the Nuggets were not interested in helping out a Western Conference rival. Caldwell-Pope opted out of his $15.4 million player option and hit the market. Dallas moved on to Klay Thompson.
The Magic were happy to pick up the pieces, grabbing what they felt was a veteran guard with championship experience who could help their young roster off the court and add the shooting and spacing they so desperately needed.
Orlando received rave reviews for its offseason -- Jeff Weltman still picked up a third-place vote for the NBA's Executive of the Year -- in adding Kentavious Caldwell-Pope. It felt like a perfect match.
One season into the three-year, $66-million contract Caldwell-Pope inked, all that is left are questions. He did not fix the Magic's shooting. In fact, he seemed to become a victim of whatever is in the water that has prevented Orlando from being a decent shooting team for the last decade.
After a season where Orlando was last in the league in 3-point field goal percentage (31.8 percent, nearly two percentage points worse than the next worst team), everyone is seeking answers. How did everyone have such a poor shooting season? How did a player of Caldwell-Pope's pedigree not deliver the one skill the team needed?
Caldwell-Pope's shooting struggles were emblematic of the team-wide issues that plagued this team.
"[The season was] not as I expected," Caldwell-Pope said at exit interviews. "My performance, being able to come over here and have a great start to the season, I think I finished a little solid. Shooting-wise, it could be a lot better. That goes into a lot. I thought my season was pretty good despite everything we've been through."
A frustrating season
Kentavious Caldwell-Pope delivered the grit and defensive determination the Orlando Magic expected. But he was a 3-and-D player. He did not deliver the "3" part. He had one of the worst seasons in his career from beyond the arc.
His 8.7 points per game were the fewest since his rookie year in 2014. His 34.2 percent 3-point shooting was the worst since the 2016 season.
And even that was boosted by a late-season surge that saw him shoot 30 for 63 (47.6 percent) during the team's final 18 games to make the Playoffs and earn the 7-seed.
That did not help him in the Playoffs. Caldwell-Pope was only 6 for 23 (26.1 percent) in the Magic's five-game playoff series. That included an 0-for-6 showing in Game 2. According to NBA.com's tracking stats, all six shots were wide-open (with the closest defender 6+ feet away).
From that basic perspective, Caldwell-Pope failed to deliver on this critical skill. He had his worst season since he became a key role player on Playoff-level teams.
"I think a different environment, the style we play is different than other places he's been," coach Jamahl Mosley said during exit interviews. "He's somebody who is going to be resilient and continue to work, and continue to find being comfortable in the system now is something we'll look forward to. Exactly what we know he is capable of doing, he will do that moving forward."
Caldwell-Pope admitted it took him longer to find his place within the new team. The Magic do not have the same quality of passing as a LeBron James or Nikola Jokic. Their offense relies a lot less on passing and more on isos and individual brilliance to get guys open.
Caldwell-Pope, when asked about what went wrong at exit interviews, said some of it was about learning how to get to his spots and work with his teammates. The early-season injury to Paolo Banchero did not help him find that role either. Injuries interrupted that integration process.
Caldwell-Pope noted he was a lot more stagnant and did not move into those open spots as effectively. The learning curve to play off of Banchero and Wagner was indeed hindered. It took a while for him to find his rhythm.
That is at least part of the explanation. But he also missed shots.
Statistically, there were not many differences between his shot profile in 2024 with Denver and in 2025 with Orlando.
Caldwell-Pope shot 40.6 percent on 4.1 3-point attempts per game last year. He shot 34.2 percent on 4.3 attempts per game with the Magic in 2025.
According to tracking data from NBA.com, Caldwell-Pope made only 39.1 percent of his 2.0 wide-open 3-point attempts per game. He made 44.0 percent of his 2.2 attempts per game in the same situation with Denver in 2024.
The Magic's offense was never going to be as efficient as the Nuggets. But Caldwell-Pope also missed a ton of shots.
"Obviously, he didn't shoot the ball the way he hoped to, but more importantly, the way he had the last five years," president of basketball operations Jeff Weltman said during exit interviews. "What accounts for that? These are questions that we've been asking ourselves. It's not just him, it's our whole team. We have a roster of guys who shot career lows. Is it just adding a shooter? Is it adding a playmaker? What unlocks our existing roster and how do we best add to that roster to fix ourselves offensively and fix our shooting production?"
A team-wide issue
It would be one thing if it were just a Kentavious Caldwell-Pope problem and this was an aberrational down year. But several players had career-worst 3-point shooting seasons. The kind of improvement the Orlando Magic hoped to see from three throughout the roster never came to fruition.
The focus on Caldwell-Pope is warranted though. The Magic spent a lot of money and put a lot of faith in him to boost the team's offense. The results were marginal at best -- a 109.1 offensive rating with Caldwell-Pope on the floor compared to a 108.9 average.
It leaves the Magic asking a lot of questions.
The team kept the faith in Caldwell-Pope throughout the season, hoping the law of averages would see him return to the mean. It never truly came for him.
And it left a lot of frustration for everyone around the Magic.