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)
That’s where this question gets tough. As revisionist history creeps in.
Kobe for Vlade as one of the dumbest trades of all-time retroactively, but the Lakers obviously knew Shaq was going to sign with them, so they traded a big for the 13th overall pick (a prospect they really liked!)
And, even though they knew Shaq was going to sign with them, they couldn’t have financially done it without moving Vlade.
Shaq for Vlade seems like an LA win. Before even throwing in Kobe.
No actual risk involved.