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Boston Celtics' Jaylen Brown (left) and Marcus Smart (right).
Despite having two of the league’s most elite talents, as well as an All-Defensive stalwart at their disposal, the Boston Celtics continue to float around mediocrity for the second consecutive season. Ever since their Eastern Conference Finals appearance in 2019-20, the Cs boast a win-loss record of just 52-55.
Throughout this span, the two Jays — Jayson Tatum and Jaylen Brown — have padded their stats, yet struggled to play cohesive basketball alongside one another for long stretches. Their questionable fit has led to mounds of trade speculation surrounding Brown, who is believed to be one of the most sought-after trade chips on the market. Similarly, the team’s longest-tenured player, Marcus Smart, has also been readily engulfed in trade chatter and is rumored to carry heavy interest from contending squads.
Still, despite struggling to stack “Ws” in the win column, and potential moves to be had, the Celtics have been bullish about keeping their core together, even when presented with the opportunity to add a two-time Finals MVP to the fold.
The Almost Blockbuster ‘That Never Happened’
Have the Celtics overplayed their hand when it comes to Brown and Smart? While both players continue to be a hot commodity on the trade market, their shine has appeared to lessen to some degree this season. However back in 2018, the two could have been reportedly packaged in a deal to acquire one of basketball’s very best in Kawhi Leonard, per Sports Illustrated’s Chris Mannix.
“They could have made a deal for Kawhi Leonard — my understanding, from kind of both sides of this—involving Jaylen Brown and Marcus Smart,” said Mannix, (via NBC Sports). “At least Jaylen Brown as the centerpiece of it all.”
Boston’s decision not to pull the trigger had Bleacher Report’s Zach Buckley wondering “what could have been,” highlighting the failed blockbuster among the “Recent Dream NBA Trades That Never Happened”:
You know how the pursuits of NBA superstars always wind up labeled as sweepstakes? Well, somewhere the Boston Celtics have stockpiled a lot of silver medals and participation trophies from previous chases that produced a lot of rumors but never actually landed a star in Beantown.
That was perhaps most clearly evident in the 2018 clash for Kawhi Leonard, as the two-way superstar tired of the San Antonio Spurs and immediately vaulted atop everyone’s list of trade targets. The Shamrocks, meanwhile, had the opportunity to put the best offer on the table, but they balked at including a top trade chip.
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Did Boston Whiff?
After missing the majority of the 2017-18 season with a highly-publicized quadriceps injury, there were lingering questions regarding Leonard’s future form, which Buckley notes could have played into Boston’s decision to steer clear.
If the Celtics were worried Leonard wouldn’t be the same after effectively losing a season to injury, they simply guessed wrong. He cracked the All-NBA and All-Defensive second teams immediately after this non-trade, rewarding the Toronto Raptors with their first world title for having the guts to go get him.
If Boston thought too highly of Brown to give him up, that’s a more defensible stance. He may never be as dominant as Leonard, but Brown has carved his own path to two-way stardom.
Obviously, Leonard showed little ill-effects in his return to the hardwood, leading the Toronto Raptors to the first NBA title in franchise history. Leonard’s 732 points during the 2018-19 postseason remain the third-most points totaled by a player in a single postseason in league history. However, his stint in Canada lasted only one season, as Leonard headed back to the states — inking a deal with the Clippers.
Could the Celtics have had a better chance than the Raptors of convincing Leonard to re-up as opposed to returning to his roots in Los Angeles? Buckley debates:
If the Celtics were simply scared off by Leonard’s uncertain future — he only had one season left on his contract at the time — that’s impossible to analyze, even with hindsight. Maybe Boston could have convinced him to stay and form a championship trio with Kyrie Irving and Jayson Tatum. Or perhaps both Leonard and Irving would’ve bounced at season’s end and spiraled the Celtics into a rebuild.
As far as fallout from what could have been, the Celtics still find themselves in a good spot. While they’ve failed to reach the postseason success that Leonard has had since exiting San Antonio, their betting on Brown proved beneficial. The Cal product has taken a major leap into stardom since, earning All-Star honors this past season. Plus, he’s five years the junior of the 30-year-old Leonard. Still, that’s not to say there wasn’t some second-guessing in the Celtics building regarding their decision.
“I do know that there’s some regret from some people within the Celtics organization about not pulling the trigger on a Kawhi Leonard deal last summer,” Mannix reported back in 2019.
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Vinny Somma is Heavy.com's former NBA & UFC editor. He previously served as the lead contributor for Heavy's coverage of the New York Giants and Boston Celtics from 2019 to 2022. More about Vinny Somma
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