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3 difficult offseason questions the Cavaliers need to answer

Isaac Okoro and Caris LeVert, Cleveland Cavaliers. (Photo by Jason Miller/Getty Images)
Isaac Okoro and Caris LeVert, Cleveland Cavaliers. (Photo by Jason Miller/Getty Images)
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Cleveland Cavaliers
Caris LeVert, Cleveland Cavaliers (Photo by Michael Reaves/Getty Images)

Should the Cavaliers bring back Caris LeVert?

Two things can be true at the same time. The first is that the Cavaliers seem to genuinely love Caris LeVert, a player who has accepted a downgrade in role to fit into a team that changed around him. He is having the best defensive season of his career and hasn’t outwardly chafed in any way at the reduction in touches. He seems like a great teammate and a positive piece of their team culture.

At the same time, the trade the Cavs made a year ago to bring him in was absolutely a mistake. They moved a first-round pick and a valuable second to bring him in, a player who was a tough fit from the start and only became more so when they traded for Donovan Mitchell. Would the Cavs rather have LeVert right now, or a wing they could have traded for last summer (say, Bojan Bogdanovic) and a top-flight second-round rookie (Andrew Nembhard, Jaylin Williams and Jaden Hardy all went in the first seven picks of the second round).

The answer is obviously door number two, but there’s no use crying over spilled milk. The question now becomes how to move forward. Should the Cavs wipe their hands of the mistake, let LeVert walk in free agency, and move on? That’s an option, and better than drastically overpaying him, but they won’t open up enough cap space going that route to replace him.

Should they re-sign LeVert to preserve the salary slot and then look to trade him midseason? Or try to get him to ink a deal fit for a sixth man and keep him in the plans moving forward? Part of their calculus will be what LeVert wants as well. For all of the fit concerns, the Cavs are in a tricky position deciding how to move forward.

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