Was Theo more successful in his 10 year run as Chicago's GM than Hoyer has been in his 4 years? Of course, the flags flying in Wrigley show that. Did the Quintana trade or the Soler/Wade Davis trade or the Kimbrel signing have anything to do with that success? No. Your argument was that 'willing to take risks' correlated to success, and then showed a bunch of examples that didn't lead to success and arguably hamstrung the beginning of Jed's time.
Theo signed Lester, Jed signed Swanson (first two years fWAR, 9.1 to 9.2). Theo signed Heyward, Jed has committed $100m to Bellinger. Maybe it's possible that the success that Theo had wasn't from trading prospects for big names, but from Rizzo, KB, Javy, Russell (acquired in a sell trade!), Hendricks, Arrieta, etc coming through the system and becoming elite players at cost controlled salaries, something that just stopped happening under Theo right around 2017.