Cavaliers: Grading 5 free agent wings from ‘no way’ to ‘yes please’

Dillon Brooks – Uh, probably

Matisse Thybulle, Derrick Jones Jr., and Dillon Brooks. That’s probably the complete list of players who can defend both point guards and large combo forwards at a high level. When you factor in offense, Brooks stands apart as the best two-way options to try and meet every need the Cavs have in a small forward.

Ideally, such a player could be tasked with guarding Jalen Brunson in a series against the Knicks and Jayson Tatum in a series against the Boston Celtics. They also would be a good enough shooter to be defended on the perimeter, and could handle the ball well enough to run a pick-and-roll.

Theoretically, Brooks brings all of these things. He’s a truly top-end defender, and his shooting ability is solid if he would carve out some of the bad shots he takes. We’ve discussed the possibility to signing Brooks in detail this offseason, and it largely comes down to this: if the Cavaliers think their team culture and leadership can help Brooks tone down the talking and sharpen the shot selection, he’s going to be the best player available at the MLE.

Those are certainly big ifs, and the Cavs may not want to bother with the headache. They are an organization that hasn’t tolerated prima donnas, and it’s possible that Brooks comes and then is just as much of a head case as he was in Memphis. If he’s willing to sign for the MLE, it becomes a difficult decision for the front office.