3. Kyle Lowry
The Memphis Grizzlies drafted Kyle Lowry 24th overall in 2006, but after two and a half seasons as a backup, he was traded to the Rockets in a three-team deal. Lowry continued coming off the bench in Houston behind Aaron Brooks before breaking out in 2010 just after signing a four-year $23.5 million deal to stay with the Rockets.
The six-foot point guard lasted just two seasons as the Rockets' starter. An infection during the lockout-shortened 2011-12 season cost him 16 games, and the Rockets decided to move on following that campaign.
Houston traded him to the Toronto Raptors in July 2012 for Gary Forbes and one first-round draft pick. The selection was used in the James Harden deal, so this worked out, but Kyle Lowry took off in Toronto. He made six straight All-Star appearances from 2015 to 2020 and spent nine seasons as their starting point guard, including leading the franchise to its only championship in 2019.
The Houston Rockets swung a deal for James Harden to make this look better, but they could have massively regretted letting Kyle Lowry go as he entered his prime. He had issues with head coach Kevin McHale, but those could have been worked out. Instead, the Rockets moved on and had to watch Lowry hoisted the championship trophy in 2019.