Will the Boston Celtics’ cautious pursuit of Kawhai Leonard prove to be a historic mistake?

Some NBA observers believe that’s the case after the Celtics’ disappointing regular season gave way to a second-round elimination from the NBA playoffs, while Leonard and the Toronto Raptors are one win over the Milwaukee Bucks away from an NBA Finals tilt with the Golden State Warriors. That current Eastern Conference dynamic might have changed had the Celtics risked more last July during trade talks with the San Antonio Spurs.

Rival NBA executives told The Athletic’s Jay King the Celtics erred in failing to approach the San Antonio Spurs’ demands for the All-Star forward. Boston reportedly declined to include any of its budding or current stars in its trade offer to San Antonio, whose head coach Gregg Popovich determined to remain competitive after Leonard’s departure.

The Celtics instead loaded draft picks into its package and took young forwards Jaylen Brown and Jayson Tatum off the bargaining table, according to King’s sources.

“… the Celtics never indicated they were willing to put top young players Jayson Tatum or Jaylen Brown into a trade package.”

San Antonio ultimately accepted Toronto’s offer of DeMar DeRozan, Jakob Poeltl and a first-round pick in the 2019 NBA Draft in exchange for Leonard and Danny Green.

One rival NBA executive now questions the judgment of Celtics president of basketball operations Danny Ainge.

“Assuming what we know (about their pursuit) is true, it was questionable at the time,” the executive said. “Now, it looks worse.”

Another executive described the Celtics’ approach to the Leonard trade talks as an “obvious backfire.”

A third executive graded apparent error as an 8 out of 10 in magnitude.

The injury problems that torpedoed Leonard’s 2017-18 season and the manner with which his relationship with the Spurs broke down almost certainly concerned the Celtics. Brown and Tatum also had just helped the Celtics reach Game 7 of the Eastern Conference Finals, and Boston probably believed it wouldn’t be prudent to risk future success on Leonard, who was entering the final year of his contract and reportedly was set on joining one of his two hometown clubs, the Los Angeles Lakers and Los Angeles Clippers, this summer as a free agent.

Nevertheless, second-guessers are prevalent in today’s NBA, and the Celtics aren’t immune to their criticism.

Thumbnail photo via John E. Sokolowski/USA TODAY Sports Images