4. The infamous Brooklyn Nets-Boston Celtics swap
In 2013, the Boston Celtics pulled off one of the biggest highway robberies in the history of the NBA. The team found a desperate trade partner in the Brooklyn Nets and made the perfect trade, sending Kevin Garnett and Paul Pierce for a slew of draft picks.
It is not like Pierce and Garnett were still at the top of their game at the time, either. This is not simply a hindsight great trade. Sure, it imploded more than we could have expected for the Nets, but the Celtics knew what they were doing and pulled it off seamlessly.
Pierce was heading into his age 36 season and was on the decline and only spent one year on the Nets before playing three more years on other teams as a mere role player. Garnett was heading into his age 37 season and played a year in a half in Brooklyn, averaging 6.6. points and 6.7 rebounds per game.
In return for two aging veterans, the Celtics ended up with the 17th overall pick in 2014, the third overall pick in 2016, the first overall pick in 2017 and the eighth overall pick in 2018.
The Celtics used these picks to either parlay it into other talents (trading for Kyrie Irving), as well as getting even more draft capital as well as the face of the franchise (swapping 1 and 3 in 2017 for Jayson Tatum).