Celtics

Kevin Garnett, Jayson Tatum & more: Ranking ‘Trader’ Danny Ainge’s 5 best trades for the Celtics

Danny Ainge retired as President of Basketball Operations for the Celtics on Thursday. Photo by Pat Greenhouse/Globe Staff

In his 18-year tenure as President of Basketball Operations for the Celtics, Danny Ainge never shied away from big moves.

His tendency toward bold deals sometimes served him well and sometimes came back to bite him. The Celtics won the championship in 2008 thanks to Ainge’s willingness to spend major assets, and the team fell apart in 2019 when the Kyrie Irving experiment failed.

Ainge’s reputation as a deal-maker earned him the moniker “Trader Danny,” which was often mocked when he didn’t come through with franchise-changing maneuvers.

So now, at the end of his tenure in Boston, what were Ainge’s best trades? Here are five that will define his time with the Celtics.

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1. Al Jefferson, Ryan Gomes, Sebastian Telfair, Gerald Green, Theo Ratliff, and two first-round draft picks for Kevin Garnett (2007)

Many NBA fans now will tell you this deal was one-sided. Some even suggest Kevin McHale did Ainge — his old teammate — a favor.

That’s revisionist history. At the time, this deal was considered a major haul for the Timberwolves. Al Jefferson had All-Star potential, and the combination of young prospects and picks was enticing.

But with the trade, Ainge completed the trio that made up the Celtics’ Big Three for the next six years, claiming one title in 2008. If Garnett had stayed healthy in 2009, and if Kendrick Perkins hadn’t gotten injured in the 2010 Finals, they might have won more. Ainge also held on to Rajon Rondo, who helped the Big Three stay in contention long past 2008.

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2. Kevin Garnett and Paul Pierce (and other pieces) for three unprotected picks plus a pick swap (and other pieces) (2013)

Ainge’s second-best move was the trade he made to fully tear down the championship team he himself created, which is pretty impressive front-office work. In exchange for two franchise legends, Ainge ultimately brought in the two Celtics — Jaylen Brown and Jayson Tatum — who will lead the Celtics into the future. He also acquired the pick that ultimately was the cornerstone of the deal that brought in Kyrie Irving.

The Irving deal, of course, blew up in his face. But as Ainge steps away and Brad Stevens takes his place, the Celtics are in good standing largely because of Tatum and Brown.

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3. Delonte West, Wally Szczerbiak and Jeff Green for Ray Allen and Glen Davis (2007)

Placing the Ray Allen trade on this list is difficult because Allen wasn’t as impactful as Garnett, but the Garnett trade wouldn’t have happened without Allen and Paul Pierce in place. Garnett reportedly had no interest in playing for the Celtics until the Allen trade made it clear he would be joining a contender.

Fans questioned the wisdom of the Allen trade at the time, but in conjunction with the rest of his moves that offseason, it proved to be one of Ainge’s more prescient decisions. He had a vision of a super team, and he found a way to create it.

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4. Marcus Thornton and a late first-round pick for Isaiah Thomas (2015)

Ainge made a surprise move at the trade deadline to bring in a scoring guard the Celtics had long admired.

No one could have predicted what would happen next — that Thomas would become one of the most beloved Celtics players of the decade over the next three years, leading the Celtics to the playoffs three times including one run to the Eastern Conference finals. Ainge himself likely didn’t foresee the extent to which Thomas would excel.

But Thomas was a borderline MVP candidate in Boston acquired for a pick the Celtics didn’t really need. The IT era, despite its brevity, was electrifying and memorable even if it never led to a championship.

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5. The No. 1 pick in the 2017 draft for the No. 3 pick and a second lottery pick (2017)

This trade, of course, was the precursor to the Celtics taking Jayson Tatum with the No. 3 pick. The only reason it’s this low is because the Celtics would likely have taken Tatum anyway — he was reportedly always the Celtics’ top option.

But the process Ainge went through was a testament to his ability as a GM. The Celtics made it seem like they might take Fultz, and in doing so, they were able to wrangle the pick that ultimately became Romeo Langford out of the Sixers. Whether or not Langford turns into a major contributor, Ainge’s foresight to not only select Tatum but also to acquire future assets in the process will stand as one of his better moments as a talent evaluator.

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