The quirk that All Might possesses is called All For One. It is a quirk that can be passed from one person to another and it gains more power each time it is passed. All Might gave Deku (Izuku) a sliver of his power by making him eat one of his hairs. If this is how it can be passed than isn't possible for that quirk to be passed to a multitude of people? Say, an army, for example.
I think yes, all might was already getting weaker as it is but could still give his power off. in the show it made it seem as if 2 people cold hold the quirk at the same time as shown with izuku and all might as there time overlapped. so possibly if we tried passing the quirk among to 2 people it could possibly work.