After the Boston Celtics 2021 season ended with a desultory first-round playoff loss to the Brooklyn Nets, who are the latest and greatest NBA super squad orchestrated by elite players, Danny Ainge announced that he will be retiring as President of Basketball Operations of the Boston Celtics. Ainge will be replaced by current Celtics head coach Brad Stevens. Stevens will start the process of searching for a new head coach.

Ainge was hired by Wyc Grousbeck and Steve Pagliuca in 2003. For eighteen years, Ainge has led the Celtics. It was Ainge’s ability to assemble a super team (Kevin Garnett, Paul Pierce, and Ray Allen) that allowed the Celtics to add banner #17 to the rafters at TD Garden. In Ainge’s tenure, the Celtics have hired only two head coaches: Doc Rivers and Brad Stevens. Without question, Ainge’s run was successful. He assembled a championship team, took on the challenge of rebuilding the Celtics after their championship window expired, and then the last few years have been rather mystifying – and probably personally frustrating to Ainge.

Succumbing to the Nets in five games, it was evident that the Celtics were nowhere near the talent level of the Brooklyn Nets. The megawatt NBA marriage of Kevin Durant and Kyrie Irving brought the Brooklyn Nets instant championship credibility, which attracted The Bearded One, James Harden, to this off-Broadway NBA production.

While the Brooklyn Nets have been ascending, Ainge’s Celtics have faced growing pains and what can best be described as a disappointing 2020-21 campaign. In no small way, the success of the franchise was deeply affected by the decision of Kyrie Irving to leave Boston at the conclusion of the 2018-19 season. In Kyrie’s two seasons in Boston, the talented point guard struggled to become the face of the franchise. He struggled to connect with younger players, such as Jayson Tatum and Jaylen Brown, and the locker room was deemed a toxic environment. As a leader, Kyrie had failed. The Kyrie Irving Experience would end with a second-round playoff loss to the Milwaukee Bucks, who were a franchise on the rise with the development of the supernova, Giannis Antetokounmpo.

When Kyrie decided to leave the Celtics, Ainge was left with no plan. The addition of Kyrie Irving had given the Celtics an elite player. An elite player who would ideally recruit other elite players to Boston. In a tough and ruthless business, where there is more personal drama than at a Kardashian ex-husbands reunion, the Celtics were left feeling the sting of what might have been. Ainge still had Gordon Hayward and two future stars in Tatum and Brown, but a player of Kyrie’s stature could have launched the Celtics on a very different trajectory.

When Ainge looks at his final years as President of Basketball Operations, he will look at four factors that significantly contributed to his stress levels:

1. Kyrie Irving’s Decision to Ghost Boston
2. Gordon Hayward’s Decision to Bid Au Revoir to Boston
3. The Decline of Kemba Walker
4. Can Jayson Tatum and Jaylen Brown Play Together?

Each of these factors still affect the Celtics today. Kyrie’s decision to flee Boston triggered Ainge’s decision to add Kemba Walker to the mix. Boston’s version of Kemba Walker is not the Kemba that thrived in Charlotte, but this version is a 31-year-old player on the decline, who struggles to stay healthy, and is the team’s highest-paid player.

The decision of Gordon Hayward to move away from his college coach, Brad Stevens, and land in the arms of Michael Jordan in Charlotte was another factor that plagued the Celtics. Hayward’s offensive presence, with his ability to move without the ball and create spacing for his teammates, was never duplicated. Hayward added cohesion to Stevens’ offense. Hayward’s move to Charlotte was motivated by a desire not be the fourth offensive option in Boston, but the first or second option in Charlotte.

And what has to be the most vexing question that caused Danny Ainge countless sleepless nights, can the 23-year-old Jayson Tatum and 24-year-old Jaylen Brown play together? Can these two emerging NBA superstars find a way to exist together and win a championship? The answer to that question isn’t clear.

Where is the track record of young NBA superstars choosing to sublimate their ego in pursuit of the Larry O’Brien Trophy? There isn’t. These mature decisions are usually made by players later in their careers, who have experienced a larger sample size of struggle and heartbreak.

Brad Stevens will have some interesting and challenging decisions to make as the next President of Basketball Operation. It should be an exciting time to be a Celtics fan.

And for Danny Ainge, he was a beloved Celtics player and then only enhanced his Green Team legacy by bringing another championship banner to Causeway Street. If only Kyrie Irving had loved being a Celtic as much as Danny Ainge.