Additional details: Cavs send 2nd to Bulls, and Blazers send lottery protected first to Bulls.

Okay, this trade very clearly aged poorly in hindsight, but I still want to understand why it happened at the time.

Chicago was tired of trying to solve the Markkanen puzzle and wanted to move him and redeem what they saw as a failure at the time. Cleveland saw hope in Markkanen (and they turned out to be right), so they got rid of an asset that wasn't doing much for them at the time now that they were well off championship aspirations.

Now, Portland.

This has all the markings of a classic move by their old GM. Working around the edges to make moves that he could sell everyone on, and wasting draft picks. Sending away a middling player on an expiring contract for a middling player on a longer contract. Sure, the logic that their draft pick would not have been worth much anyway if they made a deep playoff run was not crazy, what was crazy is believing that team would make a deep playoff run.

Just looking back on the trade with the eyes of "then", the Blazers were clearly no closer to contending, and so the pick was still very valuable. Even ignoring hindsight, this was a pretty bad trade by the Blazers.