Five Biggest ‘What-Ifs’ Of Danny Ainge Era With Boston Celtics
Sean T. McGuire
Some of the biggest "what-ifs" from the tenure of Boston Celtics president of basketball operations Danny Ainge are franchise-altering.
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Danny Ainge spent more than a quarter century with the Boston Celtics organization.

Ainge, who was drafted by the Celtics in 1981, spent his first eight NBA seasons wearing green. He was named an NBA All-Star with the organization and won a pair of NBA championships. After his playing days were over and four seasons in coaching were behind him, Ainge stepped off of the television set and took the corner office. He was named the Boston’s president of basketball operations in May 2003.

Ainge spent the the next 18 years in Boston’s front office before stepping down in June 2021. Ainge did so in order to spend more time with his family and focus on his health, though accepted a job with the Utah Jazz just 196 days later. He later admitted he needed a break from Boston. But Ainge’s time in Boston, at least in the eyes of the majority, will be remembered fondly as he helped the Celtics to the organization’s 17th NBA title following the 2007-08 season.

Nevertheless, Ainge’s tenure also included a number of questions and shortcomings in the long-awaited pursuit of Banner 18. And with Ainge stepping away from the franchise, we felt it was appropriate to reflect back on some of the biggest “what-ifs” of Ainge’s tenure with the Celtics.

Here are five of the biggest “what-ifs” Green Teamers long will ask themselves:

5. What if Ainge opted to sign Isaiah Thomas to a contract extension despite injury?

Thomas was a fan favorite in Boston due to his perseverance on and off the court. The 5-foot-9 guard, who earned the nickname “King of the Fourth” given his ability to take over games for the talent-limited-but-hard-playing Celtics, was set to enter the 2017-18 season in Boston after earning NBA All-Star nods in each of the previous two campaigns. He was entering the final year of his contract, making a modest $6.2 million when NBA salaries were drastically starting to increase. In July 2016, Thomas expressed how the Celtics better “back up the Brinks truck,” referencing the large sum he hoped to earn from the organization. To that point, his contract had been a steal and some Green Teamers agreed as they wanted his success story to continue in Boston. Ainge, however, said in January 2017 there had been no extension talks because they couldn’t happen until summer 2017. And then things changed. Thomas initially suffered a hip injury March 15, 2017, two months after Ainge’s comments, but returned just two games later. He got back to his ways, averaging 27.8 points in the next 12 games, and led the Celtics to the No. 1 seed in the Eastern Conference. Unfortunately for Thomas, he reaggravated the injury during Game 6 of the Eastern Conference semifinals in mid-May and after clearly being impacted on the court was ruled out for what proved to be the final three postseason games. So, just weeks before the Celtics and Thomas might have started talking about a contract extension, the undersized guard who relied on his ability to get into the paint and finish at the rim, was dealt a career-altering injury. It ultimately led to Ainge making what at the time was viewed as a heartless decision to trade Thomas to the Cleveland Cavaliers in August 2017. The biggest reason behind the heartlessness was Thomas’ recent loss of his sister, Chyna Thomas, in April. Thomas played the night after her death in Boston’s playoff opener and scored 33 points in honor of her birthday. It was a griping moment for the organization and for its fans — another reason behind Green Teamers’ infatuation for Thomas. But Ainge’s difficult decision to trade Thomas now is viewed as a bullet dodged. Thomas has struggled to find consistency ever since that injury during 2016-17 season. He has played just 109 games since the 2017-18 season while averaging 11.7 points and shy of 22 minutes per contest.

4. What if the Kyrie Irving situation played out differently for Ainge, Celtics?

The Celtics traded Jae Crowder, Ante Zizic, Thomas and the Brooklyn Nets’ 2018 first-round pick for Irving in August 2017. It served as a major blockbuster during Ainge’s tenure. And while it was difficult for Green Teamers to look past the departure of the beloved Thomas, the talent Irving possessed quickly caused many to overlook the price. Irving, however, went on to have a tumultuous tenure in Boston. After hinting to fans that he would re-sign with the organization following the 2018-19 season, and after starring in a Nike commercial about his jersey one day hanging in the TD Garden rafters, Irving spurned the Celtics and left after just two seasons. Irving played 127 games in Boston and averaged 24 points on 49% from the field, displaying the talent which interested Ainge in the first place. But ultimately, especially with the injury to Gordon Hayward during the 2017-18 season opener and Irving being sidelined during the 2018 postseason, the Celtics were not able to make the most of his first campaign. Irving played 67 regular-season games during the following 2018-19 season but Boston ultimately was eliminated in an Eastern Conference semifinals gentleman’s sweep. It marked the end of Irving’s short tenure, which Green Teamers certainly have not forgot about. However, given the drama that has continued to follow Irving since he left Boston and signed with the Nets, perhaps it’s another situation where Celtics fans should be happy with the way it played out.

3. What if Ainge was able to sign Kevin Durant during 2016 offseason?

The Celtics put on the full court press before the 2016-17 campaign in hopes of landing the free-agent superstar. Let’s not forget the Celtics sent a crew to the Hamptons to meet Durant that summer with then-head coach Brad Stevens, Ainge, then-New England Patriots legend Tom Brady and a number of Celtics players including Kelly Olynyk — which always will be a strange development in itself. Durant previously shared how he was “really impressed” by the team’s pitch. Ainge and the Green, however, lost out to the defending champion Golden State Warriors. Durant, who was entering his age-28 season, played the next three seasons and won two NBA titles with the franchise. It’s fair to question whether Durant’s arrival in Boston could have helped the organization win a championship (or two?) of it’s own. And given the fact the Celtics still would have had the opportunity to add current stars like Jaylen Brown and Jayson Tatum, perhaps Durant’s tenure in Boston would have lasted more than the three seasons it did in Golden State. This is one Celtics fans might never get over.

2. What if Ainge didn’t attack the 2007 offseason in the way he did?

Ainge was the well-deserving recipient of NBA Executive of the Year after the Celtics won the NBA Championship following the 2007-08 campaign. The Celtics did so after trading for sharpshooter Ray Allen and Kevin Garnett during the 2007 offseason, giving Boston its “Big Three.” With Allen and Garnett teaming up with captain Paul Pierce, the Celtics won 66 games together after starting with 30 wins in their first 34 contests. The trio clicked right away and that season proved to be the most wins in franchise history since 1986. How that offseason is viewed now, however, is much different than it was at the time. The Celtics had to part with Al Jefferson, a talented big man who was becoming a fan favorite, in order to acquire Garnett. And the standalone trade for Allen was not felt to be one that would get the Celtics over the hump on its own. Nevertheless, if Ainge didn’t make the blockbuster additions he did with Allen and Garnett, it’s possible his tenure in Boston is viewed much different now.