When the NBA season started, the Celtics were roundly considered the favorites to come out of the East and face the Warriors in the NBA Finals. They were fresh of a conference finals appearance run made without stars Kyrie Irving and Gordon Hayward. The year didn't exactly turn out that way, however, with Boston losing to Milwaukee in the second round of the postseason and the Raptors emerging out of the East on the back of Kawhi Leonard's play.

This result, along with a season full of issues, has created some regret within the Celtics front office, Chris Mannix of Sports Illustrated reported during the The Crossover podcast. He explains what would have been necessary to complete the deal and digs into why some in Boston wish they had taken a swing at Leonard. 

(Listen to the latest Crossover podcast here. The following transcript has been edited and condensed for clarity.)

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Chris Mannix: I do know that there is some regret from some people within the Celtics organization about not pulling the trigger on a Kawhi Leonard deal last summer.

Rohan Nadkarni: A lot of teams should regret that.

Mannix: My understanding from kind of both sides of this is it involved Jaylen Brown and Marcus Smart or Jaylen Brown at least. Jaylen Brown is the centerpiece of it all. They didn't do it in part because I don't think they wanted to tie themselves to two players that are going to be unrestricted free agents this summer. He was 19 at that time, they had no idea what Kyrie was going to do, but think about what the Celtics would be with Kawhi and Kyrie on that team. The kind of force they would be on both ends of the floor.

Kyrie is coming off maybe his best season as a player. He had a great basketball season. It was kind of tarnished by what he was doing off the court, but he had a great season as a basketball player. I think there's some significant regret within the organization in Boston about not rolling the dice to go get Kawhi Leonard.