The difficult question facing the Boston Celtics in the 2021 offseason

While the core of the Boston Celtics figures to remain intact for the 2020-21 season, things could get tricky next summer with so many players needing new deals.

If you’re a fan of the Boston Celtics core right now, you may be in for a rude awakening next summer. With the team set to give Jaylen Brown a raise from his signed extension and Kemba Walker‘s salary continuing to ascend, things are likely to get very murky in regards to the team’s salary cap situation.

Walker is the team’s centerpiece, and in signing him to a four-year max deal in the summer of 2019, Danny Ainge has committed to the long-time former Charlotte Hornet as his marquee superstar.

Next on the totem pole is Jayson Tatum. After struggling to make a sophomore year leap during the 2018-19 season after an impressive rookie season, Tatum has become the player many expected him to be this year before the season was suspended.

Averaging 30 points per game in February and making his All-Star game debut, Tatum’s season has gone as well as hoped for Celtics fans. He is the man-in-waiting, and figures to take over the lead spot in the C’s hierarchy sooner rather than later.

If you go by shot attempts this season, Tatum has already become the go-to guy in the offense. His total of close to 19 shots per game eclipsed Walker’s 16 or so shots from the field.

Tatum is still on his rookie deal, but he is set to see a raise before the 2021-22 season. That paired with Brown’s extension puts the C’s books on the hook for over $70 million annually between the trio of Brown, Walker and Tatum.

Then there is the Gordon Hayward conundrum. Hayward, who signed on with the team following a stellar 2016-17 season, has faltered for the most part in his Celtics stint. That said, he has shown signs of life this season and has reasonably bounced back from a devastating leg injury he suffered in his first game in green.

Hayward is due $34 million in 2020-21 via a player option he is almost certainly going to opt into. So far, Ainge has shown a reluctance to shop the former Utah Jazz star despite the fact that he plays the same position as Boston’s top two stars.

Finally, there is Marcus Smart. Smart is on a reasonably priced deal that pays him roughly $13 million annually. As one of the league’s best bargains, Smart is providing far more value than his cap figure.

That may change in 2022. In two summers, Smart is due to receive the biggest pay day of his career when his value catches up to his salary. That will be the first season that Tatum will be on his new deal, which figures to at least match Brown’s $22-26 million cap figure for the next few seasons.

With Walker’s salary ballooning to $36 million, the team will have no flexibility to spend on any new free agents. The question becomes whether or not to invest in their current core, where there is an overlap in position and skill set.

Does Ainge bring back Hayward on a new contract–likely one that starts at a lower number than his current deal–or does he let him go knowing that Smart is set to get a significant raise in 2022?

With Walker and Brown in place, and Tatum almost certainly set to cash out for his rookie-deal extension, the question then becomes this: who do you keep if you want to avoid paying a steep luxury tax, Smart or Hayward?

It’s a question Ainge will answer for the Boston Celtics next summer, via trading away one of them, letting Hayward walk in free agency, or choosing both…and paying steeply for it.