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Boys, Bye: Five Big Offseason Questions Facing the Celtics

The flip never switched on for Boston. Now it heads into a summer full of franchise-defining decisions—starting with the future of Kyrie Irving.

Getty Images/Ringer illustration

We reached the darkest timeline for the Boston Celtics right around the third quarter of Wednesday’s fate-sealing Game 5 loss to the Milwaukee Bucks:

That’s bleak … but not totally unreasonable. Asset by asset, the Celtics built a team that just seven months ago was widely viewed as the best challenger to Golden State’s dynasty. But everything came crumbling down this season in a hailstorm of scoffs and cryptic comments. The innards of the team that came one win shy of last year’s NBA Finals are still here, behind all that black gunk, yet the front office heads into the offseason facing crossroads decisions with virtually every important player on the roster—starting with Kyrie Irving. Here are the five biggest questions awaiting Boston after losing 4-1 in the second round of the playoffs:

Will Kyrie Irving return?

Irving tried, aggressively, to quash the conversation about his future at various points during the season, but there’s a reason it was such a hot topic to begin with: His choice in free agency this summer has the potential to shape not just the Eastern Conference for years to come, but the entire NBA. Say what you want about his lackluster defense or his second-round shooting slump—after claiming that he was over the “B.S.” regular season and ready for the “highest level,” Irving is still a franchise-changing player who, at 27, is just entering his prime.

No team, of course, will feel the impact of Irving’s decision more than the Celtics. If he stays, Danny Ainge will be at David Griffin’s doorstep in New Orleans the next day, cue cards in hand, ready to wrangle Anthony Davis away and turn the training wheels on his contender into monster-truck tires. If Irving leaves, Ainge and Co. will still head back to the drawing board with the guts of a good young team—and probably far less stress—but without a clear answer of how to take the leap to title favorite without sacrificing the future (more on that below).

For what it’s worth, the Celtics can outbid any other team for Irving, should he indeed opt out of the final year of his contract: Boston can offer five years, $190 million, while the 29 other NBA franchises can offer a max of four years, $141 million. But while a player with Irving’s injury history will have to consider an extra year of security, recent history—Irving’s included—suggests that where and with whom a star wants to play matters far more than how long their deal lasts.

Is Jayson Tatum trade bait or the future of the franchise?

Irving may stay, Irving may go, but the referendum on Tatum’s career is coming no matter what. A year ago, the then-rookie looked like an MVP candidate-to-be, but a season of floating around on offense, settling for midrange jumpers, and getting IRL subtweeted has sent many a Tatum stan retreating into the bushes. It’s worth noting that Tatum actually improved in his sophomore season—virtually all of his raw totals are up, and while his scoring efficiency is down, expecting Steph Curry–level shooting from 3 again, even on low volume, was a bit ambitious. Punctuating any Tatum commentary, good or bad, with his age has become the internet’s favorite gag for two years running, but here’s the thing: He’s only 21—and was only 20 for most of this season. Only five players 20 or younger averaged 15 points or more this season, and Tatum had the highest effective field goal rating of anyone of them who didn’t always shoot right at the basket. Tatum hasn’t been great, but it’s worth remembering that it took Brandon Ingram only a couple of games this spring to regain traction before a fluke blood clot issue derailed the rest of his season.

The more salient question is whether the Celtics view Irving as the root cause of Tatum’s just-fine second season. If Irving stays, Tatum should start developing a taste for boudin as soon as possible; Boston can put together a satisfactory pupu platter of assets for Davis without throwing Tatum in a trade, but Tatum is the trump card should the bidding devolve into an arms race. And if Irving leaves, Boston will need to decide whether a one-season gamble on Davis, à la Toronto’s with Kawhi Leonard, is worth parting with two low-cost seasons—plus team control over his next deal—of a 21-year-old who recently helped lead the franchise to the East finals. Keeping all the young players and leaning into the spunky, switching team that broke through in last year’s playoffs has its merits, especially for a fan base that’s had to suffer through postgame treatises on What It’s All About for half a year. But Ainge has been filling his war chest to take a run at Davis for years; will anything, or anyone, keep Ainge from getting his man?

Will Al Horford return?

Irving isn’t the Celtics’ only cornerstone player who could walk away this summer. Horford, signed to a four-year max in 2016, holds a $30.1 million player option for next season, when he’ll be 33. You’d think a player of his age and experience and recent injury history would be hard-pressed to find that sort of annual value elsewhere, but a team starved for defense and leadership—say, Atlanta, Horford’s old stomping grounds?—could replicate what the Sixers did with JJ Redick in 2017 and overpay to speed up their rebuilding process. Or Horford could prioritize the security of a long-term deal at a lower cap number rather than one final year at his maximum.

Committing to Horford past this season wouldn’t seem prudent for a Boston team entering a new era one way or another, but it will need him next season in whatever iteration it ends up with. If the Pelicans take the long view and don’t seek to pair Horford and Jrue Holiday—who, for what it’s worth, share an agent—Horford would make for an ideal frontcourt partner with Davis, a center who prefers to leave the bruisings and beatings of the position to others. And if the Celtics go young, Horford can simply reprise his role as defensive anchor and help keep the team competitive as the moving trucks come and go. It is not Time Lord’s time just yet.

Re-sign Terry Rozier?

Rozier seemed marked for trade fodder ever since he flaunted his civic pride last postseason. (It definitely didn’t work out for the last pint-sized point guard.) But whether it was because the Celtics needed insurance following Irving’s surgery or a market never materialized for a lead guard with the steady hand of a baby operating a jackhammer, Rozier lasted through his final contracted year in Boston and will head into restricted free agency. The question now regarding Rozier is the same one the Celtics will find themselves asking about virtually every young player on this roster: Can he return to last postseason’s playoff form in the absence of Irving? The guess here is no, and if the Boston brass agree, their decision-making tree becomes rather simple: match or agree to any reasonable offer in order to keep the asset, like they did for Marcus Smart last year; otherwise, let the 25-year-old pick up his ironic T-shirt business in the market of his choosing.

Extend Jaylen Brown?

As if there wasn’t already enough on Ainge’s agenda, Brown, the no. 3 pick in the 2016 draft, is eligible for a rookie-contract extension before the start of next season. If you watched the Celtics this postseason, this seems like an easy call: While Tatum came and went, Brown returned to the fearless attacking style that spurred his emergence last year and reaffirmed his station as a foundational prospect—perhaps even a better one than his Jay Teammate. If Boston isn’t sold on Brown’s shooting long term—35 percent from 3 this postseason, 34.4 percent in the regular season—they could toss him in the Davis bidding. If Boston is sold, it would be wise to lock Brown up before he proves the breadth of his offensive game either playing off of Davis or in an offense with far more shots to go around.