Coming out of the Raptors’ first preseason tilt with the Miami Heat, I was very impressed with what I saw from second-year guard, Chucky Hepburn.
Hepburn got just over 25 minutes of playing time, where he put up 11 points on 4-for-6 shooting, five rebounds, two assists, and recorded four steals. While these preseason games hold a level of importance for the main roster guys to produce effectively in early samples, I think for those further down the pecking order like Chucky Hepburn, the run they get in these samples are even more of a crucial opportunity for them to show out and prove to the coaching staff/front office personnel that they belong with the organization.
And right there alongside others like Tyreke Key, Nimari Burnett, Malachi Smith, and Jaden Bradley — it was their chance for the taking to put in strong audition tape. But like I said earlier, I thought Hepburn stood out the most from the bunch and presents real upside as another sneaky Raptors gem lying in wait.
Going undrafted in the 2025 NBA Draft, the Louisville product signed a two-way deal to join the Toronto Raptors. Heralded as a defensive standout, where he was crowned ACC Defensive Player of the Year, Hepburn looked like a prototypical Raptors pickup who matched up perfectly with their defense-first culture. Sure, Chucky is on the smaller side at just 6-foot tall (some prior reports of 6'1 or 6'2) and more of a tweener guard than a true one or two, but with some very important reps in the G League and internal development — it presented a path for Hepburn to evolve into a difference-maker at the pro level.
Unfortunately, Hepburn suffered a key setback back in January, having undergone surgery to repair a torn meniscus in his right knee, which kept him on the sidelines. But he looks back to game speed again, and while still on a two-way agreement with the Raps — Toronto has shown before that if a two-way contracted player can impress enough, they could easily get bumped with the main roster and converted into a standard contract.
Can Chucky Hepburn carve out a path to Raptors relevance this season?
With the Raptors’ guard depth where it is right now (Immanuel Quickley and Jamal Shead), the third-string spot is wide open for the taking between Chucky Hepburn and Alijah Martin. You could throw Jaden Bradley into the mix, too, but I think he’ll spend more time with the 905. Martin didn’t suit up for the Oct. 3 game, and he’s also been on my radar before as another untapped gem on the cusp of breaking out. Still, it’s hard to argue against Hepburn’s case: he could be another pesky, hard-nosed defender for the Raps, despite his size and frame.
The depth of this Raptors squad has been a focus, with everyone pointing to the usual group of youngsters poised for bigger roles: Jamal Shead, Ja’Kobe Walter, Collin Murray-Boyles, and even Jamison Battle. Hepburn might be on the outside looking in when it comes to a concrete rotation spot, but if he can keep showing offensive growth while staying a menace on defense, the Raptors will have another quality guard to explore alongside IQ and Shead.
The conversation gets a little juicy when you consider that Shead’s spot is secure thanks to his winning intangibles and floor-general instincts, but I still have major questions around his upside to impact the game offensively. If Hepburn proves to be consistent and efficient in small samples, the Raptors could expand that guard rotation to three names and find ways to use all of them.
Shead can be the usual stout playmaker with a high IQ, whether off the bench or in specific defensive lineups. IQ likely keeps his starting spot and still has folks believing in his upside as a shooter, while Hepburn could help bridge the gap and provide some extra buckets without straying from the team’s defensive culture.
I know Hepburn is far from a sure thing, and I don’t want to make him sound like a world-beater based on one game. But given what the Raptors have discovered in-house before, it’s not entirely far-fetched to imagine Chucky finding that same kind of success if he gets a fair shot. Does he need to be a rotation lock on opening night? Not exactly. But do I want to see him stick around long enough to show the Raptors why he was worth their time and belief? Absolutely.
At the end of the day, that’s how you maximize two-way spots: not just by filling a requirement, but by finding a potential breakout down the line. And at the very least, he's a gem to unleash with the 905 and their aspirations.
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