Should the Celtics Go All in or Play the Long Game?

For years, the Celtics planned for life after LeBron. They acquired draft pick after draft pick, stacked their roster with young talent, and signed a few free agents still at the beginning of their primes, all in preparation for a potential power vacuum at the top of the Eastern Conference. And then the day came—LeBron headed west. Some other team would be the protagonist coming out of the Eastern Conference, and who, if not the loaded Celtics, would it be? Then the 2018-19 season happened, and the players clashed. With their resistance to sharing minutes with one another and their proclivity for sharing information with reporters, Boston skidded to a 49-33 record (fourth in the conference) and a second-round playoff exit.

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Watching Toronto’s postseason run must sting for Boston—not only because the Raptors are in the Finals, but because of how they built the roster that took them there. The type of dish Boston had tried for years to make in a slow cooker, Toronto nuked in a microwave and threw on the table. Trading for one year of post-injury Kawhi Leonard was an enormous risk, the type of wildly aggressive move Boston’s calculating front office hasn’t really made. Danny Ainge’s most recent blockbuster deal was trading for Irving, but the All-Star guard had two full seasons remaining on his contract, wasn’t coming off a lost season, and cost just Isaiah Thomas, Jae Crowder, a first-round pick, and some change. The Celtics have built a reputation for being two steps ahead, but they’ve never put all their chips in at once.

Now, their roster could fold in half this offseason: Kyrie Irving, Al Horford, and Marcus Morris can be unrestricted free agents, and Terry Rozier is restricted. Boston is on the hunt for a deal that would bring in Anthony Davis, which, while it would accomplish the exciting goal of bringing in Anthony Davis, would probably mean parting with the faces the Celtics call their future, likely including Jayson Tatum or Jaylen Brown. It may be time for Boston to decide whether it wants to get aggressive or double down on the long game. There are essentially three different versions of the Celtics’ future:

1. The Short-Term Superteam

The logic is simple: Convince Irving to stay, trade for Davis at almost any cost, and hope those superstars can bring the team a trophy in their first season together the same way Kevin Garnett, Paul Pierce, and Ray Allen did in 2007-08. This option might be the most appealing to the Celtics, but it is also somewhat out of their hands. Other teams are just as thirsty for Davis, and there is a year’s worth of reports linking Irving to New York. Those rumors aren’t slowing down, either; multiple reports over the past couple weeks alone suggest that he is committed to the Knicks or the Nets. But Kyrie hasn’t ruled out re-signing with the Celtics, either, wrote the Boston Herald’s Steve Bulpett on Wednesday. The timing of Bulpett’s reporting is significant, as it follows Kevin Durant’s Achilles injury in Game 5 of the Finals. Much of the speculation around the idea that Irving will sign with a New York franchise has included conjecture that KD will join him. That Durant will be sidelined for likely all of next season could change things for Irving, who turned 27 in March and may be motivated to join a team that can contend immediately.

If Boston manages to bring in Davis, Irving’s supposed desire to team up with another superstar could be filled in the place he already calls home. And on Wednesday, ESPN’s Adrian Wojnarowski said that Boston’s “best chance” to retain Irving would be to acquire Davis. But because Davis’s agent, Rich Paul, has warned that the superstar forward will enter free agency in 2020 no matter where he lands, it creates a chicken-and-egg situation: If Irving commits to staying in Boston, the Celtics will be inclined to throw more assets into a potential Davis trade. At the same time, the Celtics might have to pull off the AD acquisition before getting a commitment from Irving.

Another wrinkle: Davis and Irving are both on designated veteran exception contracts, and teams can have only one such player at a time. Irving’s contract status will change on July 1, but the Pelicans have reportedly indicated that they want to trade Davis before next week’s draft. Ainge would have to do some Cirque du Soleil–level juggling to pull this off.

Paul’s comments reportedly haven’t scared Boston, which might be ballsier watching Kawhi now. But this option does carry a stark worst-case scenario: The team can’t accomplish a fantastical Finals run, Davis walks the following summer, and there’s no Tatum or young core to fall back on.

2. The Youth Movement

The silver lining in missing out on Davis and Irving would be that Boston can stay the course with Brown and Tatum. Talk of Tatum as a prodigy quieted last season—sophomores gonna sophomore-slump—but he’s only 21 years old, and Brown is 22. Plus, Boston has four picks in this draft, at 14, 20, 22, and 51, which it could use to trade up for another young talent. (Rozier could also be re-signed in this scenario, but with Marcus Smart already extended and Rozier feeling himself this summer, he may be gone no matter what.)

This makes Boston’s timeline significantly longer, and makes certain elements of the roster (such as Gordon Hayward) no longer fit. But while this roster would be a downgrade from one with Davis, at least in Tatum and Brown there is a vision that goes beyond the 2019-20 season, and it’s a future where Brad Stevens’s developmental skills will be of use.

3. A Hybrid

For the past few seasons, Boston has simultaneously built two competitive teams: its current roster and its projected roster, the one that will materialize after its young core develops. If Davis and Irving are playing in TD Garden come October, it’s because the Celtics, to some degree, surrendered that future assurance. And if it’s Tatum hitting shots in green and white, it’s more than likely because the C’s have let their dreams of a championship next season go. It’s difficult to imagine a scenario in which Boston can continue as it’s gone, having its cake and eating it too. (Which is fine, since that cake was never good enough for a Finals appearance.)

What, if anything, could keep Boston in the comfortable situation it’s enjoyed for so much of the past few seasons? Maybe Irving could be convinced to stay if the team traded for a different player, one with a longer deal and who doesn’t require as large of a return package. Maybe Boston can lure a free agent, though the team doesn’t have max-level space to throw around. Boston is in this position because years of planning and hedging—signing the big free agent in Hayward, trading for Irving, amassing the picks that turned in Tatum and Co.—didn’t lead to the perennial Finals contender that Ainge envisioned. It doesn’t get much bigger or braver than pursuing Davis. And if there were a bigger or braver option available, Boston would be pursuing that, too.