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)
Acquiring Kawhi Leonard on his last best year for demar and jakob.
Gave up being a good team to be a great team.
Won a championship.