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I may have missed this, but an initial search didn't yield anything. Also don't have my book at work, so I'm not sure if this is explicit in the wording, but I don't recall it being so.

Let's say I charge into the enemy with 2 units, let's say 5 wracks each. All the attacks are at the same initiative, and could be rolled together. The enemy is wiped out. Who gets the token?

It's randomized.

Explicitly stated in the rules for pain tokens.

indeed, random

Thanks all!