As a Celtics fan myself, I will have to say the Paul Pierce and KG trade with the Nets made by the mastermind, Danny Ainge back in 2013. #InAingeWeTrust
Now as for the details:
On July 12, 2013, the Brooklyn Nets officially announced they had acquired Kevin Garnett, Paul Pierce, Jason Terry and D.J. White from the Boston Celtics in exchange for Gerald Wallace, Kris Humphries, MarShon Brooks, Keith Bogans and their unprotected first-round draft picks in 2014, 2016 and 2018. The Celtics also received the right to swap first-rounders with the Nets in 2017.
(ESPN)Forsberg/Mazzeo: The legacy of the Celtics-Nets blockbuster
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Now at the time I was infuriated when I saw this trade. We had given up 2 legends for benchwarmers and a crap load of picks. (I didnt understand the value of these draft picks). We were just coming off a season where we were one win away from the finals. Now all we were left with was Rondo and role players.
From the Nets side, it seemed like a reasonable trade. They had good starters and entered win-now mode so they decided to pursue two experienced veterans. Unfortunately for the Brooklyn Nets, they were unable to capitalize.
Now fast forward just 2 years, Rondo has been traded but the Celtics after acquiring Isaiah Thomas, are now in the Playoffs. They have drafted a future superstar in Marcus Smart. Now lets look at present day.
The Celtics are just 2 games behind first place in the East. They have drafted another athletic wing in Jaylen Brown who is just a rookie right now.
They own the rights to the Nets pick of the 2017 draft which will definitely be the #1 overall (In a very talented draft) since the Nets are easily the Worst Team in the NBA. These picks have also put them in position for trades for superstars to make the elite contenders. (Examples- Paul George, Jimmy Butler, Demarcus Cousins but none of them happened but were possible.) The Celtics will certainly be elite championship contenders in 1–2 years.
Unfortunately for the Nets, they will struggle for a long time. Danny Ainge deprived them of their draft pick so even when they are the worst team in the NBA, they receive no compensation.
Easily the best move I have ever seen.
I may have made some mistakes, feel free to correct me in the comments.