On July 27, 2013, Boston Celtics General Manager Danny Ainge completed one of the greatest heists the NBA has ever seen, most notably trading Paul Pierce and Kevin Garnett to the Brooklyn Nets for five players and an eventual four first-round picks. Seven years later, the book has closed on Ainge’s opportunity to capitalize on the deal that he will be remembered by as an executive, and it’s time to retire the “Trader Danny” nickname he earned as a result of it. 

The full terms of the deal between the Celtics and the Nets included Boston sending Pierce, Garnett, Jason Terry, DJ White and a 2017 first-round pick which was eventually traded to the Los Angeles Lakers who selected Kyle Kuzma. The Nets sent Keith Bogans, MarShon Brooks, Kris Humphries, Kris Joseph, Gerald Wallace and what turned into four first-round picks to the Celtics. 

This trade was the first in Ainge’s mission of acquiring draft capital and assets in what appeared to be a plan to cash in his chips for a star. The team acquired first-round draft picks in 2014, 2015, a pair in 2016, 2017, 2018, 2019 and two more in 2020. Meanwhile, the team also used their own pick in each of those drafts. It’s been near impossible for Ainge to navigate the 15-man limit of an NBA roster with his avidity for the draft.  

Only three first-round picks have been shipped out of Boston during this stretch. The 2017 pick that became Kuzma went to Brooklyn in 2013. The 2015 trade that brought Isaiah Thomas included a 2016 selection in the package to the Phoenix Suns. The most recent came in 2017 when a 2018 lottery pick went to the Cleveland Cavaliers in exchange for Kyrie Irving. 

In the meantime, Boston has been able to watch the value of their acquired draft picks rise over the years. Owning potential picks from the Nets, Lakers, Los Angeles Clippers, Dallas Mavericks, Memphis Grizzlies, Philadelphia 76ers and Sacramento Kings at some point left the organization in a constant position to be in the mix for a young star. 

Among the players Ainge was reportedly in discussions about over the years included Anthony Davis, Blake Griffin, Kevin Love, Jimmy Butler, Kawhi Leonard and most recently James Harden. Boston appeared to have the trade chips available to make a move in a lot of these scenarios, but as has been the case lately, Ainge was comfortable enough with his roster and his draft picks to the point where he was unwilling to risk them. 

The team scored with the selections of Marcus Smart, Jaylen Brown and Jayson Tatum and have made trades to bring in players like Thomas and Irving. Ainge even made a few splashes in free agency signing Al Horford, Gordon Hayward and Kemba Walker to max contracts. It would be a far cry to say that Ainge has been complacent, but there’s no doubt that he failed to maximize the pieces he had at his disposal. 

Whether it be the Celtics led by Thomas, Evan Turner and Avery Bradley, the Celtics led by Irving, Hayward and Horford, or the Celtics led by Tatum, Brown and Walker, these have always been good-not-great rosters. The progression of being gritty, overachievers to a talented team with internal issues to simply being young and inexperienced has been a rollercoaster. Nobody has been happier to get back on the ride than Ainge, however. 

The landscape of the NBA has shown that a team usually needs at least two superstars if they want to have a chance at the Larry O’Brien Trophy. After both Irving and Horford left in free agency last offseason, the team was left with a mix of unproven players with Tatum, Brown, Hayward and Walker. By season’s end Tatum had asserted himself as a superstar in the league but this proved useless with the team’s supporting cast.  

Following a loss in six games to the Miami Heat in the Eastern Conference Finals it was obvious all eyes would be on Ainge this offseason. The team was going to be in the market for a starting center, three-point shooting off the bench and another potential star to pair with Tatum. All options appeared to be on the table outside of dealing Brown or Tatum. With three first-round picks, Smart, Walker and Hayward seen as trade bait, there was plenty of opportunity to improve the roster. Especially after the Bucks, Heat, Nets and 76ers had all made moves to get better for this off-season. 

According to multiple reports, the team had conversations to move up into the top six picks in this year’s draft with four different teams. These could’ve been in preparation to then flip the pick to the Houston Rockets for Harden, but no desirable deal presented itself on draft night according to Ainge. Instead, the Celtics selected Aaron Nesmith out of Vanderbilt University with the 14th pick and Payton Pritchard from the University of Oregon with the 26th pick. 

The last chance to make an impact move this offseason fell in the lap of Ainge but the opportunity was squandered. Hayward was facing a $34.7 million player option for next season, but the overwhelming sense was that he wouldn’t be with the team by the start of the season.  

The market for the former All-Star appeared to be confined to the Charlotte Hornets, Atlanta Hawks, Indiana Pacers and the New York Knicks, with the Pacers drawing the most interest from all parties involved. Being from Indiana, it made the most sense for Hayward.  

A sign-and-trade with the Pacers also made perfect sense for Boston. The Celtics and Pacers were both teams whose payrolls exceeded the cap, but the NBA allows teams to remain over the threshold if it’s done by way of a trade since the salaries have to be matched by both sides. Indiana did not have the cap space to sign Hayward outright so the only way to bring him in was through the Celtics. 

According to Gary Washburn of the Boston Globe, the Pacers had offered Myles Turner and Doug McDermott in exchange for Hayward. This would have immediately addressed the team’s need for a center and bench depth. However, Ainge was asking for either T.J. Warren or Victor Oladipo instead of McDermott. 

As the negotiations and prolonged offers began to roll in for Hayward, receiving $70 million over three seasons from the Knicks and $120 million over four seasons from the Hornets. The forward eventually opted to sign as a free agent to the Hornets, subsequently leaving the Celtics handcuffed in terms of the salary cap as they were forced to watch their third All-Star in two seasons walk out the door for nothing. 

Hayward’s departure means that his $34.7 million is off the Celtics’ books, which brings them back below the salary cap. This dramatically decreases the number of possibilities for the team as opposed to if they had traded him to be able to keep their payroll where it was. 

After missing out on Harden, Turner, and Denver Nuggets’ big man Paul Millsap, Ainge signed center Tristan Thompson to a two-year, $19 million contract in what appears to be the biggest move the team will make this offseason. Leaving the team in the no man’s land of the Eastern Conference. 

Now that all the draft picks have been spent and the team has extended both Brown and Tatum, seven years of trade rumors, free agent signings and more draft picks than Ainge knew what to do with haven’t amounted to what Celtics fans hoped they would back in 2013. Boston remains in a state of limbo trying to break into a class with the Lakers and the Milwaukee Bucks.   

There’s no doubt that Ainge has hit big on a few trades and draft selections, but what’s even more obvious is the fact that Boston overplayed their hand when it came down to their young players and overwhelming number of draft picks acquired since 2013. 

The trade with Brooklyn was supposed to be the first move in launching the Celtics back into championship contention. Ainge has traded for 10 first round picks and watched four former All-Stars come and go since the blockbuster. Despite reaching the Eastern Conference Finals in three of the last four seasons, the team appears to be comfortable with the current roster while the rest of the conference continues its pursuit of the Bucks. “Trader Danny” may have been the General Manager of the Celtics in 2013, but in 2020 it’s just Danny Ainge. 

Photo Courtesy of Christopher Evans