4. Reggie Jackson (2020) - signed with the LA Clippers
Despite being a late first-round draft pick in the 2011 NBA Draft, Reggie Jackson had a relatively strong start to his career. By his third season with the Oklahoma City Thunder, Jackson emerged as a starting-caliber guard in the league. Looking to give Jackson the opportunity to start for a team, the Thunder decided to trade Jackson to the Detroit Pistons ahead of the 2015 NBA Trade Deadline. After four-plus seasons with the Pistons, Detroit was looking to turn the page toward another era for the team. That led to Jackson being shopped ahead of the 2020 trade deadline.
However, after the Pistons failed to find a landing spot for Jackson, the two sides agreed to a contract buyout. With the chance to handpick the next stop of his career, this decision was going to be a huge one for Jackson - especially considering he had struggled mightily to begin the 2019-20 campaign. In hopes of getting back to his previous form, Jackson signed with the LA Clippers. In 17 regular season games and 12 postseason contests for LA, Jackson pretty clearly left his mark.
Jackson helped lead the Clippers to a strong playoff run in which they actually took a 3-1 series lead over the Western Conference Semifinals. Unfortunately, the Clippers fell apart in that series to the Denver Nuggets and were eventually eliminated in Game 7. Jackson would leave such an impact on the Clippers during that short late-season run with the team that he would go on to play the next two and a half seasons with the club. Interestingly enough, after falling short in their championship pursuits, Jackson would go on to sign with the Denver Nuggets where he would go on to win his first NBA title.
Being a late first-round pick, Jackson has had a pretty strong career in the NBA. While he had plenty of bright moments early on in his career, the second half of his career all began with signing with the Clippers after being bought out by the Pistons. It's certainly one of the most noteworthy buyout signings in recent history.