Boston Celtics: Marcus Smart’s seen as NBA’s 4th toughest contract decision

The future, in both the short-term and long-term, of the Boston Celtics will be decided by former head coach-turned-President of Basketball Operations Brad Stevens this summer as he determines the best course of action for the offseason.

Sticking to the status quo seems like a quick way to lose confidence in fans that believe that now is finally the time time to push all of the chips to the middle of the table and acquire a star to change the fortunes of the downtrodden squad from 2020-21.

At the same time, rash decisions could likewise leave the team in an unrecoverable bind for the next several years ala the Brooklyn Nets from 2015-2019. Giving up too many picks or dealing away a core member of the team could be just as disastrous as sitting on your hands.

Stevens has several tough choices to make this summer, but perhaps none more so than what to do with his longest-tenured Celtics, Marcus Smart. Arriving just a season after Stevens did, Smart has established himself as the defensive heart and soul of the Cs.

That said, a leap to stardom has yet to occur in Boston, and it might never come. His game is that of a defensive dog that tends to do too much offensively despite his lack of diversity in his shot profile. Attacking the rim and firing up 3-pointers with volume has become his game when the postseason rolls around, and while he averaged a career-high in assists this past season, his deal represents one of the easiest to move on the roster.

Kemba Walker’s remaining two years and $74 million is seen as the most detrimental to the team’s books moving forward. That is indisputable. But Smart’s final year on his deal could be the impetus to ultimately moving Walker’s mini albatross.

In doing so, Stevens may get to avoid what could be an awkward extension conversation with Smart next summer.

Is now the time to deal him, though? Or should the Boston Celtics make a decision closer to the trade deadline?

What to do with Smart is a conundrum, one Bleacher Report’s Dan Favale recognized in naming Smart’s contractual decision the fourth most difficult this offseason:

"Upheaval within the Boston Celtics does nothing to complicate Marcus Smart’s extension eligibility. His contract situation was always going to be thorny—largely for the Celtics.Another team might be willing to go higher than $17.2 million for Smart in 2022. He’ll be only 28 when he hits the market. A four-year contract takes him through the heart of his prime. It behooves the Celtics to get him signed rather than risk losing him for nothing down the line.Jaylen Brown, Jayson Tatum and Kemba Walker (player option) are currently on the books for a combined $95.6 million in 2022-23. Tack on $17.2 million for Smart, and the Celtics will have $112.8 million committed to four players—almost the entire projected salary cap ($115.8 million). They must be willing to foot that bill or cuts costs (i.e. Kemba) for a Smart extension to make sense, all without knowing what the supporting cast will look like that far in advance. And if they aren’t going to pay him, they’ll have to at least consider moving him."

Other names on the list included Spencer Dinwiddie–who owns a player option for the 2021-22 season–, Zach LaVine, Lonzo Ball, and Dennis Schroder.

All of them could potentially be had by the Cs, who have a need at point guard long-term and could use the scoring burst possessing LaVine could bring.

Smart, though, is the problem Boston Celtics fans need to fixate on. What happens to him this offseason will set the ball in motion for the team’s roster will look like on opening night for 2021-22 and beyond.