Kitesail Corsair

This creature has flying as long as it's attacking.

Dire Fleet Ravager

Menace, deathtouch
When Dire Fleet Ravager enters, each player loses a third of their life, rounded up.

Phyrexian Metamorph

({U/P} can be paid with either {U} or 2 life.)
You may have Phyrexian Metamorph enter as a copy of any artifact or creature on the battlefield, except it's an artifact in addition to its other types.

Captain Vargus Wrath

Whenever Captain Vargus Wrath attacks, Pirates you control get +1/+1 until end of turn for each time you've cast a commander from the command zone this game.

Dreamcaller Siren

Flash
Flying
Dreamcaller Siren can block only creatures with flying.
When Dreamcaller Siren enters, if you control another Pirate, tap up to two target nonland permanents.

Deadeye Quartermaster

When Deadeye Quartermaster enters, you may search your library for an Equipment or Vehicle card, reveal it, put it into your hand, then shuffle.

Gemcutter Buccaneer

Whenever Gemcutter Buccaneer or another Pirate you control enters, create a tapped Treasure token.
Treasures you control are Equipment in addition to their other types and have "Equipped creature gets +2/+0," equip Pirate {1}, and equip {3}.

Coercive Recruiter

Whenever Coercive Recruiter or another Pirate you control enters, gain control of target creature until end of turn. Untap that creature. Until end of turn, it gains haste and becomes a Pirate in addition to its other types.

Forerunner of the Coalition

When Forerunner of the Coalition enters, you may search your library for a Pirate card, reveal it, then shuffle and put that card on top.
Whenever another Pirate you control enters, each opponent loses 1 life.

Admiral Beckett Brass

Other Pirates you control get +1/+1.
At the beginning of your end step, gain control of target nonland permanent controlled by a player who was dealt combat damage by three or more Pirates this turn.

Dockside Extortionist

When Dockside Extortionist enters, create X Treasure tokens, where X is the number of artifacts and enchantments your opponents control. (Treasure tokens are artifacts with "{T}, Sacrifice this artifact: Add one mana of any color.")

Burdened Aerialist

When Burdened Aerialist enters, create a Treasure token. (It's an artifact with "{T}, Sacrifice this artifact: Add one mana of any color.")
Whenever you sacrifice a token, Burdened Aerialist gains flying until end of turn.