I think there’s an important clue that we’re all forgetting. That cutscene opens with the clerk showing Stranger the Steef head bounty poster, and Stranger’s initial reaction is to immediately ask “what’s it pay?”, without so much as a second of hesitation. If he wasn’t planning to take on the bounty, or had any reservations about it, that didn’t show at all until the call to Sekto was made.
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