Owlbear Shepherd

• WWizards of the Coast2022-06-10
  Official Ruling
  Owlbear Shepherd's ability has an intervening if clause, which means that it checks to see if creatures you control have total power 8 or greater both as it would trigger and as it resolves. If enough creatures have been removed or their total power is reduced to below 8 by the time the ability tries to resolve, you will not draw a card.

Rulings via Scryfall