When I was in college back in 2008, I got a student worker job with Database Services. It involved sitting in the basement of a building in a stuffy room and reviewing hundreds (thousands) of transcripts to ensure they had the proper codes written down. I found myself in need of something to listen to on my MP3 player other than music to simulate a human conversation.
That’s when I discovered my first podcast: the B.S. Report, hosted by ESPN personality Bill Simmons. It was a wholly new experience to me, and Simmons’ ability to talk about any sport with wit and irreverence was captivating. He had a profound effect on my entrance into both podcasting and basketball discourse; his “Book of Basketball” was one of my favorite books as a young person.
Simmons has a number of classic bits and personas he puts on, but one of his areas of specialty is as a trade specialist. Few mainstream media members in sports enjoy coming up with fake trade ideas quite so much as Simmons.
What everyone has to learn at some point, however, is that as entertaining and nostalgic as Bill Simmons may be, his grasp of the league is both surface-level and archaic when compared to the NBA commentary being produced by people like Zach Lowe, Nate Duncan, Dan Favale, Nekias Duncan + Steve Jones, Ben Taylor, Sam Vecenie, so on and so forth. I listen to Simmons from time to time, but I’ve moved on to those podcasts that actually understand modern basketball.
Even so, Simmon has a massive following, and when he comes up with a trade idea, the world listens. He recently reported on a trade partner for the Cleveland Cavaliers that hasn’t been frequently discussed. What was the trade that he laid out, and would the Cavs consider it?
Let’s dig deeper on the idea to see if Simmons is on to something, or simply off his rocker.
Bill Simmons recently put out a three-part podcast previewing the NBA season through the lens of each team’s over/under for the year. When discussing the Miami Heat, he and his guests started to discuss where the Heat turn to now that their efforts to land Damian Lillard fell flat.
They talked about whether the Heat may have interest in James Harden, but then pivoted to include another Miami trade partner: the Cleveland Cavaliers. Simmons proposed that a deal centered around Tyler Herro and draft compensation would be offered by the Heat in exchange for the All-NBA Cleveland guard.
Here is what such a deal could look like:
It’s been proposed before that the Cavaliers should trade Donovan Mitchell now while he is at the peak of his value rather than wait out the final two years of his deal and see him walk in free agency. Simmons references the relationship with Mitchell and the Cavs “going sideways” and that the Heat will be ready with an offer when and if that happens.
For the Heat this is a no-brainer trade. Mitchell may not quite be at the level of Damian Lillard, but he is significantly younger, healthier and less expensive on his current contract. He would give the Heat a dynamic on-ball scoring threat, and his shooting ability would allow him to pull defenders off-ball when Jimmy Butler runs actions. Of course this deal is on the table if Mitchell is made available.
What would the Cavs say to such a trade?
Let’s start with the reasons that the Cavaliers would make this trade:
Sorry, I couldn’t come up with any. The idea that this trade would even be a possibility for the Cavaliers is ludicrous. Donovan Mitchell is at a minimum a Top-20 player in the NBA, while Tyler Herro is in the upper reaches of the Top 100; Simmons’ own website ranked him at 72!
The Cavaliers were willing to give up their first-round picks at the end of this decade in the original Donovan Mitchell trade because he is young enough that those picks are likely to be late in the first round. That logic transfers over here, where Mitchell and Adebayo together would be good enough to make the Heat’s firsts from 2028 to 2030 of low value.
The Cavs are ready to win right now, and trading Mitchell for a ball-dominant one-way shooting guard and some late firsts knocks them down a peg now without the assets to climb back up again. If they were to entertain trading Mitchell (something that certainly wouldn’t happen until after this season) they would look for a trade package that allows them to continue winning with this core.
Could the Miami Heat truly be ready to offer Herro and draft picks for Mitchell? Sure. That doesn’t mean that the Cavaliers would have any chance of accepting that offer. Bill Simmons is a master at stirring up controversy and that’s about all he has accomplished with this trade idea.