Kitesail Skirmisher

three generic mana one blue mana Creature — Human PiratePower and toughness3/1

Flying

Whenever this creature attacks, another target creature attacking the same player or planeswalker gains flying until end of turn.

Encore four generic mana one blue mana (, Exile this card from your graveyard: For each opponent, create a token copy that attacks that opponent this turn if able. They gain haste. Sacrifice them at the beginning of the next end step. Activate only as a sorcery.)

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Kitesail Skirmisher rulings

2023-07-28
If an effect stops a token from attacking a specific player, that token can attack any player, planeswalker, or battle, or not attack at all. If the effect stops the token from attacking a specific player unless a cost is paid, you don't have to pay that cost unless you want to attack that player.
2020-11-10
Opponents who have left the game aren't counted when determining how many tokens to create.
2020-11-10
The tokens copy only what's on the original card. Effects that modified that creature when it was previously on the battlefield won't be copied.
2020-11-10
Exiling the card with encore is a cost to activate the ability. Once you announce that you're activating it, no player may take actions until you've finished. They can't try to remove the card from your graveyard to stop you from paying the cost.
2020-11-10
If one of the tokens can't attack for any reason (such as being tapped), then it doesn't attack. If there's a cost associated with having it attack, you aren't forced to pay that cost, so it doesn't have to attack in that case either.
2020-11-10
If one of the tokens somehow is under another player's control as the delayed triggered ability resolves, you can't sacrifice that token. It remains on the battlefield indefinitely, even if you regain control of it later.
2020-11-10
Each token must attack the appropriate player if able.

Kitesail Skirmisher 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.

Encore Rule 702.141

Encore is an activated ability that functions while the card with encore is in a graveyard. “Encore [cost]” means “[Cost], Exile this card from your graveyard: For each opponent, create a token that’s a copy of this card that attacks that opponent this turn if able. The tokens gain haste. Sacrifice them at the beginning of the next end step. Activate only as a sorcery.”