Eight questions the Celtics will have to answer in 2020

After a tumultuous 2019, the Celtics' outlook for 2020 looks bright. However, the long-term direction of the franchise will be defined in the coming months as several crucial choices will need to be made that impact the present and the future. A closer look at the decisions that will need to be made as the calendar turns to 2020.   

1. Is it time to cash in on draft assets or keep flipping them to keep a strong stash in place? No team in the NBA has done a better job of assembling an impressive collection of draft capital over the last seven years. However, a potential end date is coming on that return in 2020 with the team’s final two excess first-round picks (from MIL and MEM) both projected to convey at this point for the 2020 NBA Draft.

The Celtics already have 13 players under contract heading into next season so there will be little room to add multiple rookies to the fold for a team that intends to be a contender. Will the front office look to kick the can on a few of these assets down the line to keep the war chest intact for if/when another All-Star becomes available via trade? Or will they look to consolidate some of the picks in June or at the trade deadline to land an elite prospect or a valuable veteran piece? The decisions on those fronts could have a lasting impact on the franchise for decades.

2. What parts of the roster are expendable? There was a lot of mixing and matching this offseason with eight new players added to the fold after a huge offseason overhaul. Despite a steady run of bad health luck, the dust is beginning to settle a bit in terms of what supporting pieces on this team are essential. Grant Williams has carved out a role as a versatile small-ball big and high IQ defender. Brad Wanamaker has made the most of his opportunity as a heady backup guard. Romeo Langford has emerged of late as a valuable defensive wing. Enes Kanter’s rebounding has been a huge boost for the offense. As the C’s get healthier and try to fill some of their holes across the roster potentially via trade, the question is going to be what players are expendable if a roster spot or spots need to be opened. Will a center like Vincent Poirier (signed through 2021-22) get the boot despite limited opportunity so far. Or does a wing with a lower financial commitment/upside like Javonte Green get shown the door despite an impressive season so far? One other possibility would be moving a rookie (Carsen Edwards?) instead of a draft pick to help get a deal done and open up a roster spot. Poirier seems like the most likely candidate to go given the depth chart ahead of him at center but there are a number of paths here.

3. Are the Celtics good enough to justify a notable trade-deadline addition? The Celtics have surpassed even Brad Stevens' expectations when it comes to win-loss record to begin the year. They remain the second-best team in the East and third overall in the NBA with favorable advanced metrics that line up with their stellar record. It’s been a mixed bag of results against elite opponents (8-7 vs. +500 opponents) but many of those contests have come when the team has been shorthanded or facing a back-to-back. While it’s fair to assume that the C’s won’t be touching their top five players in any trade situation over the next month, there are enough necessary assets to add a valuable bench piece across the rest of the roster. Is Danny Ainge willing to go into his draft stash to add a piece? Could a younger player on the roster (Rob Williams? Carsen Edwards?) be used as trade bait as the C’s try to make a strong push to win in the present? The looming return of Kevin Durant to the East next year provides another obstacle down the road as the East looks like it will only get tougher in the years ahead given the age of the top talent. Will one more rotation piece make a difference for this team in taking down the likes of the Bucks or Sixers? We should have a better answer in the next month.

4. Is Theis/Kanter/Williams a workable center rotation for the postseason? To the surprise of many, the center position has been far from a weak spot for this franchise so far during the 2019-20 season. Brad Stevens has masterfully rotated through the Theis/Kanter/Grant Williams/Rob Williams combo on most nights, adjusting for matchups and whether the team needs an offensive/defensive burst. Kanter has even held up well in tough matchups against Joel Embiid on multiple occasions. The talent level in the East at the big spots is elite among the other top five teams in the conference however and ultimately matching up with those bodies is what is going to matter for this team in April and May. This group has shown it can do it on good nights but there are clearly weak spots here that can be exploited, especially on the defensive end with no clear-cut combo of elite size and defensive acumen. Even if the C’s roll with what they have for the rest of the 2019-20 season, how they fare in the playoffs will influence whether the center position remains a low priority in terms of the payroll or if a more dependable piece is targeted there via trade in the summer.

5. Can Marcus Smart regain his respectable 3-point shooting form? The hot shooting that Smart began his season with is a distant memory now after Smart’s 3-point percentage cratered to 32.8 percent before his eye infection. The reserve guard is still attempting a career-high 6.2 attempts from downtown so it’s evident that confidence is not an issue at all despite his misfires. Injuries likely took a toll on Smart for a few weeks before he sat out which dragged the percentages down but his career track record (31.2 percent) still shows that consistency is a big issue. Boston’s offense becomes far more lethal if he can force opponents to respect him on the perimeter and put up something closer toward a league average (like his career-high 36.4 percent shooting from deep last year). If not, Smart may lose out on more chances in the closing five, particularly if Brad Stevens keeps a true center in the mix for those minutes.

6. Is Kanter trade bait or a key piece of the puzzle? Stevens has done everything he can to put the center in favorable matchups for the first 30 games of the regular season and Kanter has responded with some of the best rebounding of his career and efficient scoring. Still, Kanter has remained a serious drag on Boston’s defense in certain matchups, as evidenced by the Raptors’ demolition of the C’s on Saturday night. Kyle Lowry and Fred VanVleet feasted against Kanter in the pick-and-roll and the center will have a target on his back any time he’s on the floor in a seven-game series. Can the Celtics do enough to cover up those flaws with the personnel and scheming around Kanter? Or will Stevens’ emphasis on defensive-first personnel convince the front office to flip Kanter for assets that lead to a more defensive-minded big/rebounder to take Kanter’s spot? The team is going to need a big body in Kanter’s mold no matter what to survive in the East, the question is whether he will be playable enough in those spots to live with defensively.

7. How much longer will Gordon Hayward’s career last in Boston? The 29-year-old has a massive player option looming for the 2020-21 season and has seen some of his best young teammates blossom into stardom around him. Hayward has looked like an All-Star himself during his limited healthy time on the floor, creating a potentially very intriguing conundrum for him and the franchise heading into the summer. Hayward will have to choose between locking in some long-term security and competing for a championship (something free agency in 2020 may not provide due to teams with limited cap room). Danny Ainge will have the ability to offer a long-term extension as well, but is Hayward going to be able to help maximize the young stars that this team is committed too? The next few months will provide a good answer to that.

8. Is Hayward/Brown/Tatum/Walker a sustainable championship core? The answer looked to be no from most analysts in the preseason but nearly every player in this group has exceeded expectations while healthy during the first 30 games of this season. Whether or not that is sustainable throughout 2020 is a fair question but the early signs are promising. The Celtics have the resources to keep this group together for at least the next two seasons (before Tatum’s contract extension kicks in in 2021). After that? Beyond a Hayward paycut, it’s going to be very tough to justify unless this team is a clear-cut contender every year. It’s too early from ruling that out as a possibility but the Celtics will likely use 2020 as a time to figure out whether that is a realistic path or pivot toward building around a core that is financially sustainable and competitive for the long-term.