I don't think having every exceptional talent they develop stick around for 8-10 years vs 4 or 5 is as important as its made out to be. If Made reaches his 100th percentile outcome and the Brewers have to trade him for a haul in 5 years that's not the end of the world imo. Not saying I wouldn't extend him, just wouldn't do it at top of the market like the other guys I mentioned got.
The generational wealth stuff isn't a hill that I'm trying to die on. I'm just generally a believer that humans are gonna human. Just don't think having a ton of your young guys signed for 10ish years fully guaranteed is as optimal as it may seem.
The Braves are a decent example. When all those guys signed extensions it felt like everyone thought they would be the next dynasty. Its been a bit of a roller coaster for them as a team and those guys individually since. They may have been better off trading some of those dudes after year 5?