Realistically, bad teams don't want to trade for Gobert. He doesn't fit their timeline.

So we'd have to trade him to a pretty good team to get anything back. And those teams want to contend. So they're not going to send more talent to the Jazz than they're getting back (though they can make up the difference with picks)

That means that almost inevitably, any trade of Gobert will make the acquiring team better in the next season or two and the Jazz worse. The Jazz could win in the long-run with picks, cap space, etc, but it'll be a step back in the short term.

So if the team clearly isn't good enough with Mitchell and Gobert and we only have a few seasons left with Mitchell, it doesn't make sense to make the team slightly WORSE for those few years, wasting what is left of Mitchell's time in Utah. So then we either hang onto Gobert and stay in the 'pretty good, but not really a threat' conversation and watch his and DM's value both decrease each year.... or we take a big swing in the hopes of breaking through, even if the odds aren't great.

This one gets us a player with immense upside (there's a reason he was a #1 pick, ROY, 3x All-Star, 1x All-NBA and 2x All-Defense). He's 4 years younger than Gobert and a transcendent defender, except on the perimeter, instead of near the hoop. His last three years before sitting out last year he averaged 16, 8 and 8 on 56% shooting and was an All-Star every year. There's clearly upside there.

But to get all that AND get the picks (which protects the Jazz for the case that things don't go well and they need to rebuild), there comes a lot of risk/downside as well. And the last year is evidence of exactly what that can be. And yeah, it's ugly. But that's the price you pay to get the upside AND the unprotected picks.

Key is that a guy like Simmons is someone you have to organize your team-building around. Everyone else HAS to be able to shoot. Simmons needs the ball in his hands. The team has to play fast and it can't have anyone clogging the paint. But the majority of that sounds like where the modern NBA is going anyway.