Every owner/GM needs to gamble for a team to succeed. Hindsight is always 20/20, but the truth is that every transaction is a risky move until proven worth. Freak accidents, team chemistry issues, etc are all factors you can’t measure before a trade/signing. Off the top of my head, rookie Kobe for Vlade was one of the biggest payoffs in NBA history (as for “riskiest” move, that is up for debate)
Trading Pau for the rights to Marc Gasol like 2 years before he was eligible for the NBA. Might be wrong at that but look at his senior year pic at Lausanne and tell me the Grizz FO didn’t take an insane shot and it worked out.