I had this same issue. I know what the problem was for me. I didn't play any gambit this season. The solution was to play gambit. I played 4 or 5 matches to get the 4 or 5 chess pieces he gives out.
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Really? I haven't played Gambit at all this episode, and had no problem getting the pieces from the Drifter.
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Also just playing one gambit match won't do it. I tried that. Play 5 gambit matches and then go get all the pieces.
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It might even be win gambit matches. I dk for sure b/c I won all 5/all matches I played.