Olivia, Mobilized for War

one generic mana one black mana one red mana Legendary Creature — Vampire KnightPower and toughness3/3

Flying

Whenever another creature you control enters, you may discard a card. If you do, put a +1/+1 counter on that creature, it gains haste until end of turn, and it becomes a Vampire in addition to its other types.

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Showing Shadows over Innistrad#248

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Olivia, Mobilized for War rulings

2016-04-08
You decide whether to discard a card as the triggered ability of Olivia, Mobilized for War resolves. If you do, the rest of the ability’s effects happen before any player may take actions.
2016-04-08
If the entering creature leaves the battlefield before the triggered ability of Olivia, Mobilized for War resolves, you may still discard a card. The rest of the ability has no effect.
2016-04-08
If you discard a card, the creature only gains haste until end of turn, but the +1/+1 counter and Vampire subtype remain indefinitely.

Olivia, Mobilized for War keyword rules

Flying Rule 702.9

Flying is an evasion ability.

A creature with flying can’t be blocked except by creatures with flying and/or reach. A creature with flying can block a creature with or without flying. (See rule , “Declare Blockers Step,” and rule , “Reach.”)

Multiple instances of flying on the same creature are redundant.