I can tell Servant Leader, Borrowed Time and Bad Omens is not a Triumph-awarding combo.
Let me guess, it's just the older Gambit and Reckoning gear that counts, isn't it?
Asking for a friend who is exactly like me.
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Hey there, Only the original Gambit Weapons from Forsaken (Season 4) count for this. Those are the weapons included in he Playing for Keeps Collection Badge. Specifically, you need Hazard of the Cast, Bygones, Trust, Distant Relation, Pillager, Parcel or Stardust, Dreaded Venture, Bad Omens, or Malfeasance.
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It's been a minute but I would assume bygones, spare rations, and bad omens would count. You can pick them up fairly cheap from drifter.