The fact that DL made a trade didn't automatically make it "serious risk". Any trade comes with risk but a trade for Conley is a rather low-risk one. A proven vet who came with all the known qualities in his games such as never winning the conference or even his own division, no all-star or all-nba selection, that makes him a rather safe bet with low upside. We kind of increased the risk ourselves by giving away more assets than we should.
A true "all-in" high risk trade would be the Raptor's trade for Kawhi, who just came out of a injury-riddled season while also being on the last season of his contract. If Raptors came away empty last year, they could basically be going into the full rebuild as all their pieces fall apart. I mean, they traded the best player in their FRANCHISE HISTORY for Kawhi. If they failed to deliver last season, their GM will certainly lose his job as many Toronto fans vows to never watch another game of theirs again.
What's the worst that could happen to us if the Conley trade fails to deliver?(well, it already did, but he's still got one more season to go) We will still have DM and possibly Rudy to help us compete for the next 3-4 years at least. it's not "all-in" or "high-risk", far from it.