Four years ago, the Celtics had just traded Paul Pierce and Kevin Garnett to the Brooklyn Nets and were completely tearing the team down to rebuild. Just two years later, they made a surprise playoff appearance. Two years after that, they finished atop the Eastern Conference in the regular season and made a run to the Conference Finals. And, just as importantly, Danny Ainge has masterminded the entire thing without giving up a single one of his prime assets.

Ainge has signed and traded for other team’s castoffs. He’s given out long-term contracts that looked questionable at the time and turned out to be major steals years later. He’s hoarded his picks and cap space to be in position to land a superstar, while also letting Brad Stevens develop young talent on his current roster.

Last season, Ainge started moving the rebuild forward in a meaningful way when the Celtics signed Al Horford. They were far enough along to secure a meeting with Kevin Durant. This summer, as he did last summer, Ainge is dreaming big again.

Boston is position in a spot where we’ve rarely seen a team. By virtue of nabbing undervalued assets like Isaiah Thomas and Jae Crowder in trades and the draft picks Ainge acquired from Brooklyn, the Celtics are good now and could be even better in the future. The NBA has never seen a team make the playoffs multiple years in a row while also picking near the top of the lottery in each of those seasons. It’s a rebuild for which there is no blueprint. For everyone who screams “Trade the picks for a star!”, you have an equally loud voice yelling back “Keep those picks and build a dynasty!”

While both approaches have merit, it seems like Boston has neared a tipping point. Last summer, they were close to landing the top two free agents on the board. This summer they’re in the mix for the top free agent (of those who might actually change teams) in Gordon Hayward. In addition, Ainge is lining up to add a second major player, with Paul George the top rumored trade target.

To get there is a complicated path and will cost the Celtics a lot of their depth and likely some of those assets Ainge has been hoarding. First, to clear enough cap space to even entertain a max deal for Hayward, Boston will have to renounce all five of their free agents. Gerald Green is on a minimum contract and could return for the same price later in the summer, so that one is no big deal. James Young’s future in Boston was sealed when the Celtics didn’t pick up his fourth year Rookie Scale option. Amir Johnson and Jonas Jerebko are good soldiers who have done everything asked of them, but every battle has some casualties.

The one free agent that will give Ainge pause is Kelly Olynyk. Olynyk was Ainge’s target in the 2013 NBA Draft and he traded up to get him. The Celtics have patiently watched him develop over the last four years into a quality big man. He was a key to their Game 7 win over the Washington Wizards in the Eastern Conference Semifinals. To dispatch him for just cap space is something no one wants to see, but is a necessary evil.

Then you get to the non-guaranteed contracts. Jordan Mickey hasn’t improved enough in his two seasons with the club for the team to worry about waiving him. Tyler Zeller was given a larger contract that most thought he would get, solely for the purposes of being a trade chip. It looks unlikely that Boston can use him in a deal, so he’s out the door as well. Demetrius Jackson, by virtue of the minimum scale change in the new CBA, is more costly to cap space to waive than he is to keep. That, and that alone, keeps him the roster.

But, even with saying goodbye to almost half the roster, the Celtics still aren’t there. They come up just shy of max cap space for Hayward or any other max free agent in his tier. That means someone else has to be shipped out of town, and that puts eyes on Terry Rozier or Marcus Smart. Both have some modicum of trade value and Boston could gain another pick for the pile and clear the necessary cap space to sign Hayward, so one of them goes. Now the team can move forward with adding Hayward.

At that point, it becomes a game of chicken with the Pacers for George. Will Ainge blink and add additional assets to an already strong offer? Or will Kevin Pritchard have to acquiesce get what he can for his departing superstar?

If the Celtics do add two stars this summer, they have precious little depth remaining. They can remedy that by using the room exception, accelerating the development curve for Jaylen Brown and Jayson Tatum (who were each draft third overall in 2016 and 2017) and filling out the roster with veterans for the league minimum. In addition, rookie Ante Zizic, who was a draft and stash player from 2016, will likely hold down a key spot in the big man rotation.

The far less likely option is that the Celtics kick the can down the road a little more, sign a targeted veteran or two to a short term deal and get back at it next summer. The challenge with that approach is that Thomas, Smart and Avery Bradley are all free agents in the summer of 2018. With all three deserving of healthy raises over their current bargain deals, this is Boston’s last real shot at meaningful cap space.

Ainge has been criticized for being reluctant to go all in to improve his roster. Many feel he wants to roll over assets and continue to be good, with an outside chance at being great if all those assets develop. His counter has been that because the Celtics have so many picks and good players on good contracts, that teams ask for the moon in trade negotiations. He refuses to overpay based on the simple logic that he can, so he should.

To be at this point, just four years after kicking off what looked like it would be a lengthy rebuild, is incredible. To even get meetings with the top free agents is something Boston couldn’t even pull off when they were good. Behind Ainge and one of the NBA’s best coaches in Stevens, Boston is a destination now. Players have taken notice of how great Stevens is, how Ainge is ruthless in pursuit of winning, and how much talent there is on the roster now with plenty of room to improve.

Everything has been leading to Danny Ainge having one big summer where his grand plan comes together. Maybe this summer is it. Maybe it isn’t. But to even be in this position is remarkable. And eventually, even if just by sheer volume of high draft picks, everything will come together at some point. In Boston the tagline goes “It’s not luck” layered over images of players hard at work on their craft. But some luck, paired with hard work and a treasure trove of assets, could put the Celtics in position for banner 18. And in Boston, good regular seasons and playoff runs are nice, but titles are all that matter. It is on Ainge to deliver the next one. 

Offseason Details

Guaranteed Contracts (7): Avery Bradley, Jaylen Brown, Jae Crowder, Al Horford, Terry Rozier, Marcus Smart, Isaiah Thomas

Partial/Non-Guaranteed Contracts (3): Demetrius Jackson, Jordan Mickey, Tyler Zeller

Potential Free Agents (5): Gerald Green (UFA), Jonas Jerebko (UFA), Amir Johnson (UFA), Kelly Olynyk (RFA), James Young (UFA)

“Dead” Money on Cap (0): None

First Round Draft Pick(s): Jayson Tatum (3^rd), Guerschon Yabusele (2016), Ante Zizic (2016)

Maximum Cap Space: $33,187,999

Projected Cap Space: $17,786,828