Summary
Leonard had some big moments for the Trailblazers in the 2019 playoffs, hitting shots and making plays in the pick-and-roll. Unfortunately for Leonard, those moments have been few and far between during his career, and Leonard fell out of Miami's rotation in the 2020 playoffs, despite starting for essentially the entire regular season, as the Heat went smaller with Crowder at the four and gave all the backup center minutes to Kelly Olynyk. Leonard was traded to Oklahoma City mid-way through the season, and was waived by the Thunder. He also was suspended briefly for some comments he made in a Twitch live stream, which could affect his market as a free agent this summer.

Leonard fit in nicely as the stretch big to play alongside Bam Adebayo, even if it only worked during the regular season, and that could provide a template for other teams to value Leonard in a similar way. While Leonard has shot great at 42% or better from three each of the last four seasons, he did so on a low number of attempts, and has often been a little gun-shy to let it fly from deep.

Leonard has some really defensive limitations, as he is very slow-footed and does not provide rim protection either, but has looked improved on that end. If Leonard ends up hitting free agency this summer, he will also be coming off a season in which he missed essentially the entire year, so that could hurt his value.
 
Cap Considerations
Leonard was waived by the Thunder this season, and has yet to be signed by an NBA team. Teams will have multiple ways to sign Leonard as even teams without cap space could possibly use any of the Non-Taxpayer MLE, Taxpayer MLE, or possibly even the Room MLE or Bi-Annual Exception to sign him. There's also a chance that Leonard could be had for the minimum.