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His fate in the Barry dies segment of Jill's scenario varies depending on whether it was the original game or the remake of the Resident Evil:
In original version, he will be killed should player not wait for him to return with a sling of rope, once the player goes to investigate a hole in the ground. If player continue further into the underground passage without waiting for Barry, this triggers the event where he won't return at the very end to save Jill from Wesker. He will then be found dead soon after, from what was likely attacks from the Chimera creatures that are roaming throughout the laboratory.
In remake version, Barry will die if player don't return to him his magnum he during last confrontation against Lisa Trevor (though even if he is given his gun he can still die should Lisa knock him off into the chasm below during the battle). Another is during the very end against the T-102 Tyrant on the helipad; if Barry is still alive, he will then assist as a friendly NPC against the monster. Though he is just as vulnerable as the player and can be killed by it; he must also reload his magnum when necessary, though he has infinite ammo.
In Revelations 2, after breaking a gate with a crane mechanism, Barry says "Ha! Who's the master of unlocking now, huh?", which is a reference to his infamous Resident Evil quote about Jill's skill with lockpicks.