Danny Ainge has never been one to not make an aggressive move, and he made two within a decade.
In 2007, The former Celtics president of basketball operations swung a draft-day trade with the Sonics. Seattle sent Ray Allen and the 35th overall pick, Glen Davis to Boston in exchange for Delonte West, Wally Szczerbiak, and the fifth overall pick, Jeff Green. In July of the same year, the Celtics acquired Kevin Garnett for Al Jefferson, Ryan Gomes, Sebastian Telfair, Gerald Green, Theo Ratliff, cash considerations and two first-round picks. The deal was the largest number of players traded for one single player in NBA history, but it paid off.
The Celtics went on to win the championship in the 2007-08 season and made the 2009-10 NBA Finals. Paul Pierce and Kevin Garnett led Boston to three Eastern Conference finals in five years, but Ainge was not one to let the Celtics remain steadfast.
In the 2013 NBA draft, Boston shockingly traded its franchise stars to the Nets. The deal sent Pierce, Garnett, Jason Terry and DJ White to Brooklyn in exchange for Kris Humphries, Gerald Wallace, MarShon Brooks, Kris Joseph, Keith Bogans and three first-round picks, plus the right to swap first-round picks in 2017.
Ainge was immediately lambasted for the trade. Wallace carried a three-year, $30 million contract and the other players in the deal were nowhere near All-Star caliber players. Despite their advanced ages, Pierce, Garnett and Terry were seen as players who could still contribute to a title contender, which the Nets were projected as with the trio joining All-NBA guards Deron Williams and Joe Johnson. The team also featured rising young center Brook Lopez, All-Star Andrei Kirilenko and first-year head coach Jason Kidd.
The Nets appeared to be primed to win multiple NBA championships. But little did everyone know was Ainge was playing the long game.
Brooklyn only made it as far as the Eastern Conference semifinals — the first year of the trade — and continued to regress to eventually being the worst team in the NBA. During those years, the Celtics overachieved with Brad Stevens, and while not every pick hit for Boston, it only needed to hit on two.