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)