NBA Daily: The Boston Celtics’ In-Flux Future

A year ago, the entire NBA knew what team had the most on the line in the 2018-19 season. After trading DeMar DeRozan, All-Star, franchise cornerstone and fan-favorite, for Kawhi Leonard on the last year of his contract, the Toronto Raptors had to win and win a lot.

The consensus conclusion was that, if Toronto could at least challenge for the title, be that by reaching the NBA Finals or perhaps even losing in a competitive Eastern Conference Finals, then Leonard may have reason to stick around. If not, he was assuredly set to leave.

Of course, the Raptors won the Larry O’Brien Trophy and Leonard left, anyway. Toronto got its prize, making the trade worthwhile; Leonard nonetheless underscored how imperative winning immediately was.

On the surface, no franchise faces such a pressing necessity for success. Dig deeper, though, and one contender may already be facing an expiring clock on its current core.

The Boston Celtics currently enjoy a wing-centric, young roster. Point guard Kemba Walker may be the newest signee, but two years ago that hype surrounded Gordon Hayward. When Hayward signed a four-year contract for $127.8 million, it was presumed there was no chance he would decline his player option worth $34.2 million in the final year, 2020-21. Then minutes into his Celtics tenure, Hayward suffered a gruesome ankle injury and all previous assumptions went out the window.

Healthy enough to at least play last year, Hayward was distinctly Boston’s fourth or fifth offensive option. His up-and-down season finished with averages of 11.5 points, 4.5 rebounds and 3.4 assists with a harsh 33.3 three-point percentage. He clearly had not returned to his previous form. If those struggles continue, then Hayward will absolutely pick up his player option.

A few times toward the end of last regular season, however, Hayward flashed semblances of his former self. He scored 30 points at the Golden State Warriors in less than 28 minutes, including going 4-of-6 from deep, in early March. In back-to-back games — Nos. 79 and 80 for the Celtics — he scored 25 and 21 points, going 14-of-19 from the field combined, adding 15-of-16 free throws. Even if Hayward was not pouring in the points, he contributed, snagging 10 rebounds to go along with 13 points in a late March loss to the San Antonio Spurs. And that aforementioned 30-point game, it came along with seven rebounds and four assists.

That was the player Boston signed, the player robbed from the viewing public by a freak injury on 2017’s opening night.

There is a reason to think those highlights were more than just flashes, but rather precursors of that player’s return. When Paul George suffered his compound fracture in the summer of 2014, his subsequent late-season cameo for the Indiana Pacers did not look promising. In 2015-16, he racked up the counting stats but did not show the continued development once expected. George shot 37.1 percent from deep and had an effective field goal percentage of 49.0. A year later, those numbers jumped to 39.3 percent and 53.4 percent, respectively. They have remained closer to that range in the two years since.

If Hayward follows a similar timeline, needing a full season on the court between his injury and his return to All-Star status, it could put Celtics president Danny Ainge in a tough position.

Hayward will be 30, now with an injury history, and looking at the potential to be one of the top free agents in the summer of 2020. The other candidates are Kyle Lowry, DeRozan and Anthony Davis, and it would be a decent surprise if any of the three left their current teams.

A productive 2019-20 could make Hayward ponder one more big deal. It probably would not be a four-year contract, given his age and that worrisome ankle, but there may be a three-year offer waiting for him a la Paul Millsap’s current deal with the Denver Nuggets. Signing a rejuvenated Hayward to a three-year, $90-100 million contract with a team option in the final season would not be seen as a bad deal by many.

But it would be a deal the Celtics would not be able to afford unless Ainge wanted to part ways with either of his young jewels, wings Jayson Tatum and Jaylen Brown. In this hypothetical, presume both Tatum and Brown sign maximum rookie contract extensions. If Andrew Wiggins can get one, they each should. Their 2021-22 contracts, plus Hayward’s theoretical, Walker’s freshly-inked and Marcus Smart’s current deals would cost …

Walker: $36.0 million
Hayward: ~$33 million
Brown: ~$31.6 million
Tatum: ~$29.3 million
Smart: $14.3 million

TOTAL: $144.7 million in a year when the salary cap is currently projected to be about $125 million with a luxury tax threshold estimated at $151 million.

Not to mention, Ainge would still have the rest of his roster to fill.

The decision would be an easy one for Ainge, the ultimate asset stockpiler. Tatum and Brown on long-term deals are better assets than a 30-year-old Hayward on a short-term deal. Despite his relationship with Boston head coach Brad Stevens, Hayward would presumably be heading to the third team in his NBA career.

This creates a dichotomous dynamic for the Celtics in 2019-20. Their best chance at contention comes with Hayward at his efficient best, fitting well with quickly-developing Tatum and Brown, all around the offensive centerpiece of Walker. That ideal construction would also short-circuit their chances of keeping Hayward around in 2020-21. Even if he does not find the skillset that made him a max contract free agent in the first place and thus picks up his player option, the clock is ticking on Hayward’s time in Boston.

The Celtics will not be able to feasibly keep all three of Hayward, Tatum and Brown to new deals as their current ones roll off the books.

Boston is not as all-in on this season as Toronto was a year ago, but the Celtics have more to worry about than anybody else in the NBA. Their best chance at playoff success has a one-year shelf life.