The Boston Celtics have always had a knack for building great teams. From the Red Auerbach era to the current regime led by Danny Ainge, their savvy moves have resulted in winning a league-best 17 NBA championships.

It is quite surprising, then, that even with all the things they’ve done, their last NBA title was more than a decade ago. Since their last Larry O’Brien trophy in 2008, three teams have won at least two titles (the Los Angeles Lakers, Miami Heat, and the Golden State Warriors), with the Celtics only having one finals appearance and four conference finals appearances to show for it. While other teams would love to have the Celtics’ resume over that span of time, it seems uncharacteristic for a storied franchise, especially in a sports city like Boston.

Ainge has been Boston’s President of Basketball Operations since 2003, but the former Celtic’s trades for Ray Allen and Kevin Garnett in the summer of 2007 immediately vaulted Boston into title contender status. It brought in quick results as Boston clinched the NBA title (over their archrivals the Lakers no less) that very season. It was with the best single-season turnaround in league history.

His legacy-defining move, however, would arguably be the trade he pulled off with the Brooklyn Nets on June 28, 2013, which sent Garnett, Paul Pierce, and Jason Terry to the Nets for Gerald Wallace, Kris Humphries, Marshon Brooks, Kris Joseph, Keith Bogans, first-round picks in 2014, 2016, and 2018, and the right to swap 2017 first-rounders. Celtics fans initially were up in arms with that trade as it meant that they shipped away the core that won them the 2008 title and set them into a rebuild.

From that trade alone, however, Ainge was able to select Jaylen Brown with the third overall pick in 2016, Jayson Tatum in 2017 with the third overall selection (after trading the first overall selection to the Philadelphia 76ers for their pick), and used the 2018 first-round pick to acquire Kyrie Irving from the Cleveland Cavaliers. Trading back from the first overall selection in the 2017 NBA Draft to select Jayson Tatum was a ballsy move that gave them a star and also threw a wrench into the 76ers’ process.

The early returns were promising as then-rookie Tatum and the rest of the young Celtics took LeBron James and the Cavaliers to seven games in the Eastern Conference Finals despite losing Gordon Hayward to a gruesome leg injury in the first game of the season (coincidentally against Cleveland).

Their rookie returns post-Nets trade also paled in comparison performance-wise against the Lakers and merit-wise when matched against Philadelphia, whose tandem of Joel Embiid and Ben Simmons could not lead their team past the Eastern Conference Semifinals.

However, even as the likes of Tatum, Brown, and Marcus Smart developed, the team could never get over the hump. While the Celtics have played in three of the last four Eastern Conference Finals, they have struggled this season.

Currently, the Celtics are in seventh place at 23-24, yet they are tied with the Miami Heat and are a game ahead of the Indiana Pacers. This may have been partly due to the early season absence of Kemba Walker and the loss of Tatum, Grant Williams, Tristan Thompson, and Robert Williams to the NBA’s COVID-19 protocols.

Their most recent loss to the New Orleans Pelicans (who are 12th in the Western Conference) exposed the lack of depth and sloppy play that is otherwise surprising considering how long head coach Brad Stevens and his system have been in place. It also didn’t help that Ainge’s latest trade deadline acquisition in Evan Fournier missed all his 10 shot attempts in his debut.

The numbers also show that the Celtics are right in the middle of the pack on both ends of the floor. They are 15th in the league in points allowed (111.3), while they are 16th in points per game (112.3). Boston is naturally a deliberate team considering the skillsets of Tatum and Walker, with their pace of 98.0 good for the 20th in the NBA.

Ainge’s trades may have been the stuff of legend, but his free agency track record has not panned out as expected. His signings of Walker, Hayward, and Al Horford have largely been misses. Hayward’s return from injury made him feel like an odd man out, while Horford helped make the Celtics good, but not great. Meanwhile, Walker has so far struggled mightily even as he is surrounded with more talent than his days with the Charlotte Hornets.

Perhaps the knock on the Ainge regime more so in the past 10 years has been the relatively slow transition from accumulating to reaping the fruits of his shrewd moves. The Lakers themselves had Kobe’s twilight years, a six-year playoff drought, brought in LeBron and AD, and won a championship during that same stretch.

Even the Nets were able to form another “Big Three” with Irving, Kevin Durant, and James Harden in a span of two seasons. They’ve suddenly emerged as the favorites to win the Eastern Conference after also signing former All-Stars Blake Griffin and LaMarcus Aldridge to round out their rotation.

While the onus on winning lies with the players and the coaches, Ainge will have to make the right decisions with a win-now mindset as his franchise cornerstones inch closer to their peaks. Adding veterans to shore up depth would naturally be the next move, but finding players complementary to Tatum, Brown, Smart, and Walker would be of greater importance.

Teams are more often than not judged by the championships they win and titles have so far been more dreams than reality for the Celtics. The objective is as clear as day, but Danny Ainge and the Boston Celtics will have to figure out how to get over the proverbial hump enroute to an NBA championship. After all, other teams that were previously way behind the curve have already surpassed them and won titles to boot.