In a move that continues to haunt the Boston Celtics, the team’s decision to trade away their No. 30 pick in the 2020 NBA Draft has emerged as one of the franchise’s most regrettable missteps in recent memory. The player selected with that pick? None other than Desmond Bane, now widely regarded as one of the NBA’s premier shooting guards and a cornerstone of the Memphis Grizzlies before his recent trade to the Orlando Magic.
The trade, executed to offload Enes Freedom’s salary in a contract dump to the Memphis Grizzlies, seemed pragmatic at the time. Boston’s roster was already brimming with young talent, and the front office likely viewed the No. 30 pick as expendable. However, as ESPN’s Zach Kram aptly noted, this decision has aged like milk left out in the summer sun. “Nobody expected the No. 30 pick to develop into the sort of player who’d one day command four first-round picks in a trade,” Kram wrote, underscoring the magnitude of Boston’s oversight.
Desmond Bane, despite being slightly undersized for a two-guard, has proven himself a rare gem—a two-way force who combines lockdown perimeter defense with a silky-smooth shooting stroke. A career 41% 3-point shooter, Bane’s ability to stretch the floor and guard multiple positions would have made him a seamless fit in the Celtics’ system. Imagine a lineup featuring Bane alongside stars like Jayson Tatum and Jaylen Brown—a tantalizing blend of defensive tenacity and offensive firepower that could have elevated Boston’s already formidable roster.
Instead, Bane has thrived elsewhere, first becoming a linchpin for the Grizzlies and now poised to transform the Orlando Magic’s backcourt with his scoring and shooting prowess. His trade to Orlando this summer, in exchange for a haul of assets, only amplifies the sting of Boston’s initial decision to let him go. As Kram put it, “Bane would have been a perfect fit in the Celtics’ system,” offering the kind of high-volume shooting and defensive grit that mirrors the contributions of Derrick White—yet with the added advantage of youth and a longer career runway.
At the time of the trade, the Celtics’ rationale was understandable: clear cap space, streamline the roster, and prioritize immediate competitiveness. But in hindsight, the move feels like a gut punch. Bane’s development into a player worth multiple first-round picks has left fans and analysts alike wondering what could have been. Would Bane’s presence have accelerated Boston’s championship timeline? Could he have been the missing piece in their quest for consistent dominance?
To their credit, the Celtics have hardly been derailed by this blunder. The team hoisted the 2024 NBA championship trophy and remains a powerhouse with a bright future, poised to contend for titles for years to come. Yet, the what-ifs linger. Bane’s skill set—his ability to knock down threes at a high clip while holding his own defensively—would have complemented Boston’s core perfectly, potentially making an already elite team unstoppable.
As the NBA landscape evolves, the Celtics’ decision to trade away Desmond Bane stands as a cautionary tale of the risks inherent in draft-night deals. While Boston’s championship pedigree remains intact, the missed opportunity to nurture a homegrown star like Bane will likely remain a sore spot for fans, a reminder of the one that got away in the pursuit of short-term roster flexibility.