This was not how this season was supposed to go. This is not what GM Danny Ainge envisioned when he built this roster. This was not the plan.

Boston came within a single game of making the Finals last season. The Celtics have a rising superstar in Jayson Tatum. They have a defensive anchor and ultimate glue-guy in Al Horford. They have Jaylen Brown, who has at times resembled a young Paul George or Kawhi Leonard. They have Terry Rozier, who some considered the best backup point guard in the league. They have Marcus Smart and Marcus Morris, two bulldogs who energized a relatively passive team.

Oh, and they were adding Kyrie Irving and Gordon Hayward.

Yet here we are; the Celtics are bound for Cancún, not the Eastern Conference Finals.


Boston enters this summer with the ability to approach the offseason in a variety of ways, which is both a blessing and a curse.

On the bright side, they don’t have any bad contracts on the books (see: John Wall, Russell Westbrook, Chris Paul). They have the opportunity to actually improve the roster. Other teams like the Rockets, Thunder and 76ers could enter the offseason after similarly disappointing seasons, but have virtually no flexibility to improve their teams.

On the other hand, there’s an uncomfortable amount of uncertainty surrounding this team. Kyrie Irving and Al Horford have player options; Irving is a lock to enter free agency, while Horford could go either way. Terry Rozier is a restricted free agent. Marcus Morris is a free agent. Jaylen Brown is up for an extension and will likely demand near the max. Tatum and Smart are under contract, but are floated in trade rumors daily.

Put it this way, the only certainty is that Gordon Hayward will be a Celtic next season.

So, what can the Celtics do this offseason? There are infinite possibilities and after trading Isaiah Thomas two years ago, Ainge has proven that anything is on the table.

Is an Anthony Davis trade coming?

A few months ago, nearly everyone thought the Celtics offseason plan was fairly cut and dry: resign Kyrie and trade for Davis. Boston had the best theoretical package, but they could not make the trade until this offseason. When New Orleans held onto Davis through the trade deadline, everyone assumed they were waiting for Boston’s godfather offer.

Does anybody remember who is the GM of the Celtics? Danny Ainge does not overpay in trades. He got Kyrie Irving for an injured Isaiah Thomas and the 8th overall pick.

I had my doubts back in February about Boston trading for Davis, and they’ve only grown stronger. There are three reasons why I don’t think Boston will trade for Davis this summer.

Jayson Tatum’s Value

Tatum has long been the crown jewel of Boston’s package for Davis. The 21 year old rising star led the Celtics in their playoff run last season and he dunked on LeBron James in Game 7 of the Eastern Conference Finals.

I’ll be honest, Tatum’s value did not go in the direction I expected. I thought at the trade deadline that Tatum could have another sensational postseason and prove to be too valuable to trade.

Instead, the opposite has occurred. Tatum struggled and arguably may not be a worthy centerpiece for Davis anymore. Pelicans’ GM David Griffin could use Tatum’s struggles as leverage to force Ainge to include Jaylen Brown in the deal as well. However, we know Ainge is a notoriously shrewd GM and does not overpay in trades; he will not include Tatum and Brown.

New Orleans might have Better Alternatives

Back in January, I said that Philadelphia had a better trade package if they were willing to put Ben Simmons on the table (at the time, they were not). If the Sixers lose Game 6 tonight and Simmons struggles again, maybe Elton Brand becomes willing to move on from Simmons.

The Clippers have stockpiled an impressive collection of assets and can afford to be more aggressive than Boston. The Clippers would have a better chance at resigning Davis than Boston and seems likely to add Kawhi Leonard as well.

If the Knicks win the draft lottery and the rights to Zion Williamson, New York immediately becomes a major player in any Davis trade talks. Zion’s draft rights are arguable one of the top five trade assets in the entire league.

The Lakers offer may not have changed, but Dell Demps’ petty ass is out in New Orleans and David Griffin is a big fan of Brandon Ingram.

Beauty is in the eye of the beholder, so it’s impossible to judge what Griffin believes to be the most valuable trade package. One thing is for certain: Boston is no longer the Pelicans’ only option.

Kyrie Irving’s Free Agency

Boston is now in a Catch-22. They could deal for AD as a way to recruit Kyrie to stay. But if they traded for Davis and Kyrie still walked in free agency, they’d be screwed. Davis would likely walk himself in 2020, leaving the Celtics with Gordon Hayward and literally nothing else.

On the other hand, if they don’t trade for Davis, why would Kyrie stay?

The fever dream of Irving and Davis on the Celtics is still technically possible, but it would require Ainge making the biggest gamble of his life. Considering the man just had a heart attack, I’d bet he’s going to play it safe. Anthony Davis will not be a Celtic.

What are Boston’s Other Options

If trading for Davis is off the table, and I think it is, Boston still has endless options this offseason. Resigning Irving and “running it back” seems out of the question after the way this season went. This roster will look significantly different next season.

Boston could let Kyrie walk in free agency and build around the young core of Tatum and Brown. This would alleviate the pressure on Hayward to return to All-Star form, as the Celtics championship window would be pushed back a bit.

Ainge isn’t stupid, though. If he truly wants to move on from Irving, there is a smarter way to do it. Boston could try to sign-and-trade Irving to his preferred destination; maybe New York for Mitchell Robinson or Los Angeles for Lonzo Ball. This route will allow the Celtics to build around Tatum, Brown and the young guys, while adding to the young core. At the end of the day, Irving is a valuable asset – it would be foolish to lose the asset for nothing.

This seems to be the option that most Celtics fans, or at least Bill Simmons, want Ainge to take. They are done with Irving’s me-first mentality and want Tatum to be the face of the franchise. Richard Jefferson said on The Jump today that his top priority would be executing a sign-and-trade for Irving. I would agree.

This offseason is critically important for the franchise. The next decade of Celtics basketball hinges on the decisions that will be made in the coming months. Furthermore, when two players the caliber of Irving and Davis are available (not to mention Kevin Durant and Kawhi Leonard), the future of the league is at stake this summer.