It absolutely does depend on the conditions but we do not know what they were.
The question is does the pick transfer if conditions are met or does the pick upgrade if conditions are met?
I'm willing to bet it's not an upgrade to a 6th if conditions are met.
Usually, with "pick transfer" conditionals, the conditions are "on the roster for x games" or "played x% of snaps."
I'm betting it's on the roster for x games and he has a very solid chance of triggering that. Of course, if it's an "active roster" or "x snaps" trigger, then it probably won't transfer.
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