Cleveland Cavaliers
Best first-round selection: 2019 - 5th pick, Darius Garland, PG
Darius Garland is good at basketball. He's a bit undersized, but he can shoot the lights out of the gym, he's athletic and quick, and he's really grown over his five years in the league. The Cavs drafted a future franchise cornerstone, and for that, Garland's the guy. Even if the Cavs end up trading Garland this offseason for one reason or another, it doesn't take away from how good of a draft pick and player he is.
Best second-round selection: 2014 - 33rd pick, Joe Harris, SG/SF
Joe Harris is a three-point marksman. The Cavs selected Harris with the third pick in the second round. He's been a lethal three-point shooter in the league for over a decade now and is easily the choice here for the Cavs' best second-round pick.
Biggest draft-flop: 2020 - 5th pick, Isaac Okoro, SF
Luckily for Anthony Bennett, his draft class falls one year short of being able to be included. For this reason alone, Isaac Okoro is the pick. He's been fine, but teams don't draft strong, athletic wings with the fifth pick to be fine. Okoro is a solid NBA player, but he was an easy reach in hindsight with Devin Vassell, Tyrese Haliburton, and Tyrese Maxey all selected well after him.