Why the Raptors should chase Haywood Highsmith on the buyout market
What has this season come to? Am I really about to sit here and write an entire piece convincing you that the Raptors should ‘chase’ a guy who just got waived from one of the worst teams in the league? To pick him up from a team that just cut him to make room for Ochai Agbaji, the guy the Raptors shipped out to balance the budget? You’re darn right I am. And no it’s not just because the Raptors have been one of the worst shooting teams in the entire league. Well, it’s mostly because of that. But It’s also because he would provide more than shooting, he would fit like a glove with this team.
Highsmith, out of Wheeling University, went undrafted in 2018 and opted to sign a two-way contract with the Philadelphia 76ers. Over the next three years he bounced between the Delaware Blue Coats (the Sixers G-League team) and various teams overseas before eventually landing a ten-day contract with the Miami Heat. Then another one. And then another one. Eventually he landed a guaranteed contract, and played a combined 213 games across four seasons with the Heat (including 80 starts) before tearing his mensicus on August 8th, 2025. On August 15th, he was shipped to the Brooklyn Nets in a salary dump trade. Newly healthy and ready to contribute there will be a plethora of teams looking to add the versatile wing.
Why do I tell you all this?
Because doesn’t that sound like a prototypical Raptor? A guy who worked his way from the bottom, earning his place in the league after years of battling? A guy who has something to prove after the Heat salary dumped him and the Nets waived him just as he was ready to play? That sounds like a Raptor to me. We’ll get into the actual basketball fit next, but in terms of work ethic I think he’ll fit right in.
I don’t think there’s any argument that the Raptors biggest struggle this season has been shooting the ball. The team ranks 25th in three point accuracy and that’s because every player that’s supposed to be a shooter, can’t hit the broad side of a barn. Only Brandon Ingram, Immanuel Quickley, and Sandro Mamukelashvili have maintained above-average efficiency.
Highsmith has proven his ability to consistently knock down outside shots. In fact, his three point percentage has actually risen as his attempts have gone up over the years. In the 2024-25 season, Highsmith played in 74 games (starting 42) for the Heat, and hit 38% of his 3.1 three-point attempts per game. While that is influenced by shooting 44% from the corners, he also hit 34% from above-the-break, which would rank 5th amongst the Raptors regular rotation (6th when you include Jamison Battle). None of these are eye-popping numbers, but they’re solid and they’re consistent. And right now the Raptors could use some consistency.
At six-foot-five, his 220lb frame allows him to impose himself in a way that Gradey Dick or Ja’Kobe Walter are incapable of doing, and it affords him the opportunity to play in a wider variety of lineups. He’s an above-average finisher at the rim, and finishes strong through contact, converting 27.8% of his shooting fouls into and-ones. He runs the floor well too. Last season he scored 1.14 points per possession in transition, which would be tied with Dick for 5th best on the team. His efficiency would rank 5th as well.
Defensively, he has above average steal and block rates (for his position) and he’s decent on the offensive glass. For the Heat last season the team was half a point better defensively when he was on the court, nothing groundbreaking, but he’s not a liability. In the Raptors ultra-switchable defensive lineups he could slot right in.
Realistically, the buyout market isn’t netting you a fix-all player. It never does. Maybe Highsmith doesn’t crack coach Darko’s rotation, but he would be an option. A different look. Depth in a roster that hasn’t gotten what it’s needed from it’s bench guards (outside of Shead). Besides, what’s the risk? You sign him to a minimum contract and it doesn’t work out, who cares? Now, maybe you could convince me the Raptors would be better off converting one of the two-way guards — Alijah Martin or AJ Lawson — to a standard contract. But Highsmith provides a higher level of experience, he’s been to the highest levels of playoff basketball, he scored 18 points in Game 1 of the 2023 NBA Finals!
Anything the Raptors would need of him he does well, and he would add another level of versatility, consistency, and experience they don’t currently have. If the Raptors are looking to add playoff-ready talent from the bargain bin, they won’t find anyone more readily available and primed to slot into the Raptors rotation than Highsmith. Get it done Bobby.
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