The complicated history of Danny Ainge’s post-Big Three years

The immediate aftermath of the Boston Celtics' latest season hasn’t exactly sent Danny Ainge riding off into the sunset after it was announced that he’d be stepping down as Boston’s President of Basketball Operations.

The Celtics had no chance of beating the Nets without Jaylen Brown. But that they faced such a steep challenge in the first round as the underdog of the 2-7 matchup was an indictment by many on Ainge’s ability to construct a roster capable of landing in a more favorable position.

Unfortunately, that has been the narrative surrounding Ainge in these last few years, that he failed or wasn’t good at his job.

Never mind that he built the last Celtics championship team in 2008, one that also returned to the Finals in 2010, or that Boston will be home to two of the brightest young stars the game has today for the foreseeable future.

After fleecing Brooklyn with that trade in 2013, Boston was supposed to be the team of the future, only to watch several teams pass them by as they headed in the opposite direction.

Three conference finals appearances in four years would be enough for many teams, but the Celtics aren’t most teams. Championships are the goal for one of the most decorated franchises in all of sports. Anything less is a failure.

Ainge started strong in the post-Big Three era but couldn’t stick the landing. Contrary to popular belief, that’s not all his fault.

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When analyzing these last handful of years, it’s important to give Ainge the credit he’s unquestionably earned.

There was a consensus top-2 in the 2016 NBA Draft: Ben Simmons and Brandon Ingram. After that, the success of any player was up in the air and Ainge selected the raw Jaylen Brown.

Since then, Brown has blossomed into an All-Star, and a pillar of the Celtics' future alongside Jayson Tatum, but people weren’t exactly singing Boston’s praises when they drafted him No. 3 overall.

“Brown is a solid player for them, but you have to wonder what could have been here and if they could have capitalized on this differently,” wrote Sam Vecenie at the time, giving them a B- for the selection.

Whereas many were pining for Kris Dunn or college phenom Buddy Hield, Ainge knocked it out of the park with Boston’s highest draft pick since 1997.

The following year, Ainge had no hesitation relinquishing the No. 1 overall pick and the chance to draft Markelle Fultz, the consensus top selection. Tatum was Ainge’s guy all along. He got the best player in the draft while filling his asset cupboard a little more in the process by moving down two spots in the trade with Philly.

Boston also signed three All-Star free agents in free agency in a four-year span: Al Horford, Gordon Hayward, and Kemba Walker. For a franchise that hasn’t traditionally been a prime free-agent destination, Ainge has to get some props for playing some part in that.

Hindsight has done a number on two of those deals. Horford was a valued piece during consecutive conference finals runs. Hayward, on the other hand, never lived up to his billing as the All-Star Boston thought it was getting. And many Celtics fans are currently drumming up hypothetical trades to ship away the last two years of Kemba Walker’s contract.

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But the notion of hindsight both here and with other examples is what makes some of the Ainge criticism feel out of place. Because of the many unfortunate shortcomings that befell Boston, he had little to no control over many of them.

Is Ainge to blame for Hayward’s freak injury that prevented his Celtics tenure from being as prosperous as many had expected? Was Kemba not viewed as the perfect replacement for Kyrie Irving in the summer of 2019? The Ringer’s Paolo Uggetti certainly thought so at the time.

“The change from Irving to Walker feels seamless—swap one scoring All-Star point guard for another... Irving may be the better player, but Walker might be the better fit.”

Speaking of Kyrie, trading for him was unquestionably the right decision at the time, independent of how his time in Boston ended. Fans loved Isaiah Thomas and the lack of loyalty shown to him was horrible, but the idea of backing up the Brinks truck for a 5’9’’ point guard was the concern nobody in Boston wanted to address. Ainge made sure the Celtics never had to and upgraded at the position at the same time.

With Irving leading the way, Ainge had built a team expected to challenge the mighty Warriors in the Finals. Is it really an indictment on the team builder that the team he built had too much talent? Was he supposed to know of Irving’s shortcomings in a leadership role he hadn’t yet held as a veteran ahead of time? Would you have wanted that to be the dealbreaker in a trade anyway?

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The one area where Ainge warrants criticism is with the multitude of draft picks he had at his disposal, but maybe not in the ways you might think.

With all of Boston’s first-round picks and many others at his disposal, Ainge had the chance to improve a team that was clearly on its way to contention, if not already there. Instead, he banked on his ability to unearth a gem and failed.

He hasn’t really hit on any of his lottery or late first round picks of late. But if you have a problem with that, go look at the track record of every front office decision maker to see if theirs is any better. Odds are, it probably isn’t.

His most notable later first-round selection was Robert Williams III, who hasn’t been healthy enough to be a consistent presence despite having shown immense potential.

There is no justification for a perennial playoff team looking to improve its title odds making SIX first-round picks in the last two summers. Those picks could’ve helped acquire a player you have near-complete assurance will aid the current iteration of the team.

The majority of draft picks lose their value the more they materialize over time. A team’s first-round pick at the beginning of the season could theoretically wind up anywhere, but months of regular-season games shrinks hypothetical outcomes for better or worse and for Ainge, it was for worse.

Sacramento and Memphis finished with better than expected records in the consecutive years Boston held their first-round selections. That’s hardly a worthy excuse for Ainge’s unwillingness to relinquish them.

The same applies when it comes time for the NBA Lottery and when a team ultimately makes its selection. The more possibilities a pick offers, the more you can get for it on the trade market.

Ainge could’ve made a favorable deal in the offseason rooted in the same allure he fell for in consecutive years. He didn’t when he undoubtedly should have, and the Celtics are worse off today because of it. Players like Aaron Nesmith, Payton Pritchard, Romeo Langford, and Grant Williams could eventually eventually be a part of a strong stable of role players, but with Tatum and Brown in the fold and the clock ticking on their rookie extensions, circumstances called for Ainge to act more boldly.

Should that be the lasting image of his legacy running the Celtics for nearly two decades? It will be for some, but it should also a bit more complicated than that.