6. Cleveland Cavaliers
Going back to the Cleveland Cavaliers is a difficult concept for Derrick Rose up front. His previous stint with the Cavaliers was brief albeit saddening. He couldn’t stay healthy once again and didn’t wind up playing even two dozen games in a Cavs jersey before he was released.
A healthy Rose could inject life into an otherwise mostly inept bench for the Cavs in the backcourt. Depending on where the Cavs land in this draft lottery, Rose could be joining in on a good situation in Cleveland. This is a rebuilding team, so he could have the freedom to play more of his style of basketball at a more comfortable place.
The main point of appeal that could draw the connection between Rose and Cleveland is the idea of bringing him in as a mentor for the former Alabama Crimson Tide point guard Collin Sexton. It seems like the front office in Cleveland is set on investing in its 2018 lottery pick with Sexton. He could definitely thrive under a veteran mentor like Rose.
A lot of the situations that are positive for Rose to fall into next season are going to be in low pressure markets where the media and fan base aren’t as rabid. That’s the issue with him landing with a team like the New York Knicks or the Chicago Bulls. It just so happens those are the two teams he spent the bulk of his career with.