Can the Boston Celtics feasibly retain their three main wings past the 2020-21 season?

This upcoming season will determine a lot about the roster structure for the Boston Celtics moving forward. By the summer of 2021, the team will have to make a decision on whether or not they should potentially hand out three max contracts to their prized wing trio.

As the 2019-20 NBA season rapidly approaches, one of the biggest storylines pertaining to the Boston Celtics is whether or not Gordon Hayward and Jaylen Brown can have career season… in a contract year. Hayward’s free agency is contingent on whether or not he decides to exercise his $32.7 million player option for the 2021 campaign.

Brown, on the other hand, can pick up his qualifying offer come seasons end and potentially cash in on the 2021 NBA free agent bonanza. However, he will likely look to secure a longterm contract, and there will assuredly be no shortage of teams vying for the 22-year-old’s services.

Regardless of whether or not Hayward and Brown’s free agent decisions are postponed to the 2021 offseason, Jayson Tatum will too be in line for negotiations on a new deal with the Boston Celtics.

With this, Danny Ainge will have his work cut out for him in trying to decide on whether one, two or all three of the aforementioned players are worth holding onto in two years time. In the end, while their decision will certainly be based on if the organization wants to retain all three, the more pressing matter is whether or not they feasibly can.

The roster, as it stands, is top-heavy with guards and wings, but are severely lacking in their front court talent pool — specifically at their center slot. Is it a good idea for the Boston Celtics to pay three wings an excess of $30 million when, combined, the current center rotation makes under $15 million per season?

It could be. After all, the Golden State Warriors had four max players at the one through four positions and ruled the NBA until Kevin Durant and Klay Thompson suffered severe injuries during this past NBA Finals.

We all know Hayward’s ceiling, as he proved to be All-Star worthy in the season prior to his devastating ankle injury in 2017. If he can come back to such heights this season — as many are anticipating — the 29-year-old could prove himself worthy of one last massive payday. On top of this, If Tatum and Brown can become wings at the level of Durant and Thompson — while bold, it’s still in the realm of possibility — they too would be deserving of having the Brinks truck backed up.

Until that happens, the Boston Celtics need to wait and see who is deserving of the pay-dirt and who fits into the team’s longterm outlook. The 2019-20 season is the first step in finding answers to these luxury tax bill-related questions.