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Chucky Hepburn could be a good fit with Raptors facing cap challenges

July 12, 2026
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LAST VEGAS — The NBA is in kind of a weird place — and no, this story is not about the Kawhi Leonard saga. That is its own category of weird. 

What I’m referencing is how on one hand the business is booming in ways that are almost unimaginable from even a decade ago, let alone a generation or two ago. 

Don’t worry, I’ll get around to how this affects the Toronto Raptors at the NBA’s Las Vegas Summer League in a minute, but allow me some context first.

As a simple shorthand for the robustness of the NBA economy: the Raptors’ longest-serving NBA player this coming season is Jakob Poeltl, who will be playing his 11th season in 2026-27. 

He was drafted in 2016. At the time, the NBA salary cap was $70 million, or $85 million when adjusted for inflation. For 2026-27, the salary cap is $165 million, more than double or nearly double, depending how you look at it. 

Either way it’s a lot of money, which is how Poeltl has $104 million remaining on his contract — a topic for another day. 

The NBA splits its basketball-related income evenly, for the most part, with the 30 owners sharing about half of the $11.68 billion the league took in last year and the league’s players dividing the remain $5.84 billion. 

But somehow, there still isn’t enough money. 

Earlier this week, San Antonio Spurs star Victor Wembanyama raised some eyebrows when he signed a five-year contract extension for $252 million. The shock wasn’t the amount of the contract; it was that it wasn’t enough.

By waiving a bonus structure that would make him eligible for a $303-million contract if he made an all-NBA team, won MVP or Defensive Player of the Year — hardly a stretch given he was first-team all-NBA and Defensive player of the Year last season — Wembanyama has given the Spurs more wiggle room to sign players that can help him win a championship. He’s taking less so the Spurs can do more. It’s admirable, but raises the question of how teams can share in nearly $6 billion in revenue and not have enough money to sign the players they need, so the players end up taking less.

One of the biggest moves of this off-season was the Boston Celtics’ decision to trade five-time all-star Jaylen Brown to the Philadelphia 76ers. Even with Brown coming off an all-NBA season and scoring a career-high 28.7 points per game, Boston judged that the three years and $183 million left on his contract would put them into too much of a bind when it came to building out the rest of their roster. 

The villain here is the way the NBA’s salary-cap structure — in particular the penalties that are incurred for going over the first apron in team payroll ($209 million this year) and especially the second apron ($221.7 million) — has effectively put a hard cap on team spending. 

So, what about all this is relevant to the Raptors at Summer League? 

Well, you might have heard the Raptors are planning (hoping?) to acquire Leonard. And if they do, they will have almost no financial flexibility this season. And if they sign him to a two-year extension worth about $123 million, they’ll be just as limited next season, maybe even in a tougher spot.

In that scenario, finding good players who can play on cheap contracts is a must for the Raptors.

Summer League is a good place to find them. 

The 23-year-old point guard is very much trying to feel his way back to game sharpness after being out since early January following knee surgery that ended his rookie season. The heady six-footer made a good enough impression playing point guard for Raptors 905 that Toronto kept him on his two-way contract all the way through his rehabilitation and kept him on a two-way deal for this upcoming season. 

He struggled with his shooting for the second straight game, although he was still effective as the Raptors outlasted the Houston Rockets 102-89 on Saturday to even their Summer League record at 1-1. Hepburn scored just two points and was 1-of-5 from the floor but had eight assists and was a team-best +25 in the win. 

Hepburn excels doing things smaller point guards have to do to have a chance to be successful: pressuring up the floor to force opponents into mistakes; manipulating the defence to create good looks for teammates in the second half of the shot clock when the first actions have failed; and generally getting his team organized on offence and preventing opponents from doing the same. He’s struggled shooting here but shot 38 per cent from three in the G League before his knee injury. His goal, he says, is to prove he’s a knockdown three-point shooter. It would fit perfectly with his ball-handling and pick-and-roll game. 

But Hepburn’s game is more than numbers. 

As a returning player and given his point-guard DNA, Hepburn is being counted on to lead the Raptors at Summer League, a role he’s more than comfortable with. 

“Just having been around the organization already, kind of been knowing what we’re going through, I’m trying to have that voice out there,” said Hepburn. “And I have to find my voice as well because I know that obviously that’s going to be needed up top (with the Raptors’ NBA team), too.”

He certainly understands his job description. Last year while he was injured, he said he spent a lot of his down time watching smaller guards find ways to excel in an NBA setting. He came to appreciate how teammate Jamal Shead was so good at drawing offensive fouls while navigating screens. He’s done it four times in two games in Las Vegas.

“That’s a great thing being hurt, I got to learn from guys like Jamal Shead, how he guards, and how he he’s able to create offensive fouls just doing little things like that from a shorter point guard perspective are winning plays that that organizations love,” said Hepburn. 

Realistically, Hepburn’s opportunities with the NBA version of the Raptors will be relatively limited this season. Toronto has Immanuel Quickley and Shead ahead of him on the depth chart and they can always use Scottie Barnes as an oversized point guard when required. But one injury can change that. 

And in the long view? The Raptors could be in the market for a point guard, especially a cost-effective one. It’s simple NBA economics.

The Raptors aren’t likely going to be in a situation like the Celtics were this season where they felt they had to deal Brown, a former Finals MVP. 

But presuming Leonard is on board, they will have about $182 million tied up in just seven players on guaranteed deals. And that’s without RJ Barrett on the books. He will become an unrestricted free agent after 2026-27 if the Raptors don’t offer him a contract extension. 

Will they have enough, for example, to sign Shead, the culture-setting, third-year guard who has such a find for them in the second round of the 2024 draft? 

You would like to think so, but in the ‘apron era’ where superstars are taking pay cuts and teams are trading Finals MVPs, the Raptors’ top-heavy payroll could create problems. Shead — who will be a restricted free agent after 2026-27 — might have to go elsewhere to get paid what he is worth. It’s the same kind of economic pressure that meant Toronto had no real shot at keeping Sandro Mamukelashvili this past off-season . 

It might be a little easier next summer because Shead will be a restricted free agent, giving the Raptors the right to match any other offer, but they might not have the means to do it. 

It’s the harsh reality of the present-day NBA,, where teams are spending more than ever, but somehow still have to make tough decisions around the margins. 

It’s why Summer League is important and why Hepburn is a player worth paying attention to as the games unfold in the desert. 

For the second straight game, Collin Murray-Boyles watched his Summer League teammates from the bench with a splint on his right index finger. It’s not considered serious, but he is day-to-day with no word on if he’ll be available when the Raptors play on Monday. It’s a similar story with second-year guard Alijah Martin, who has a sore knee. 

After a spectacular Summer League debut, rookie wing Allen Graves was a little more subdued against the Rockets. The first-round pick held his own with nine points, three rebounds, a steal and two assists in 27 minutes, but it was a step down from his 22-point, 13-rebound, three-steal, two-block outing on Friday. Speaking with him afterward, he acknowledged that playing for the second time in as many nights may have had his batteries down just a little bit. 

Seth Lundy hit six of nine threes and led all scorers with 23 points. The 26-year-old free agent shot 41.9 from three as a rookie in the GLeague in 2023-24 but has had his progress derailed since then due to a severe ankle injury. The six-foot-four wing has looked smooth and athletic in two games in Las Vegas so far.  



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