I know the saying goes: "Don't dwell on the past," but since it's the offseason and the Raptors are approaching a pivotal turning point for the franchise, I can't help but reflect on some of the missteps and what-ifs. One move I look back on with deep regret — hindsight being 20/20 — is the Raptors' decision to draft Malachi Flynn in the 2020 NBA Draft, right before Desmond Bane was selected immediately after him.
Now, to be fair, you can't really come down too hard on the Raptors for their choice with the 29th overall pick in the draft; at that stage, it's either a hit or a miss — it's that straightforward. I also can't say many people expected Desmond Bane to be a game-changer, just as I held confidence that Malachi Flynn would flourish with the Raptors. But flourish with the Raptors, he didn't.
Raptors drafting Malachi Flynn in 2020 was a major misstep
Flynn's time in Toronto was largely marked by stifled development and a lack of true breakthrough. I didn't expect Flynn to become a superstar, but even in a limited role as the secondary point guard off the bench, I can recall very few instances where he looked like he was solidifying a long-term spot within the Raptors' pecking order.
It wasn't until new head coach Darko Rajakovic began utilizing him that I felt Flynn was gradually finding his footing and starting to become a part of Toronto's plans. However, Toronto eventually included Flynn in the OG Anunoby trade to New York, and he was later shipped out to Detroit. Fast forward to 2025, and Malachi Flynn is no longer in the NBA — he's playing overseas.
On the flip side of things, let's take a look at what Desmond Bane has accomplished since being drafted 30th overall in the 2020 NBA Draft. He quickly established himself as a key young contributor for the rising Memphis Grizzlies, becoming part of a promising core alongside Ja Morant and Jaren Jackson Jr.
Bane had a breakout year in the 2023-24 campaign, averaging 23.7 points on 46.4% shooting from the field, 38.1% from three, along with 4.4 rebounds, 5.5 assists, and one steal per game. He largely stepped into a primary role in the absence of Ja Morant. Last season, Bane continued to prove his effectiveness — scoring at will, playing solid defense, and showcasing his playmaking skills. To everyone's surprise, however, he was traded in a blockbuster deal to the Orlando Magic this summer, where his value blew expectations out of the water.
Bane was moved in a deal that sent four first-round draft picks from Orlando to Memphis, along with a first-round pick swap, and two players: Kentavious Caldwell-Pope and Cole Anthony. For a guy selected 30th overall, Bane has certainly surpassed expectations. While it’s narrow-minded to assume his career would have unfolded the same way if he had landed in Toronto, you can't discount that Bane was truly the real deal coming into the NBA — even if he was an older prospect and largely off Toronto’s radar.
You can't win 'em all, but I doubt there's a Raptors fan out there who doesn't feel this one stings just a little bit.