No. 1: Kevin Love
The first name that likely popped into the heads of many Cavaliers fans upon clicking on this list was that of Kevin Love. The former Minnesota Timberwolves big man (and current member of the Miami Heat) joined the Cavs via trade the same summer that LeBron James returned to bring a title to The Land.
Love may have struggled with untimely injuries during a couple of the Cavaliers’ postseason runs, but he was a valuable regular-season player and only increased his role in 2018 after Kyrie Irving left. A player once defined by his on-ball offense and rebounding was asked to spot up in the corner, and to his immense credit, he transformed his game and helped the Cavs win a title and make it to the NBA Finals a whopping four-straight times.
The problem came in the summer of 2018. Dan Gilbert was once again eager to show that his team was not going to fold upon the departure of LeBron James, and to that end he offered Kevin Love a lucrative contract extension to stick around. Then, instead of moving Love while he still had value, they kept him around on their losing team and watched injuries and malaise set in, nearly derailing Love’s career and providing the Cavs a whole lot of nothing when they ultimately bought him out five years later.
Love could have returned a hefty package of players and/or picks if traded early in the process, but instead, the Cavaliers held onto him through some combination of pride and stubbornness. It ultimately provided them very little and is a prime example of holding onto a player for too long.