Spectral Sailor

Flash (You may cast this spell any time you could cast an instant.)
Flying
{3}{U}: Draw a card.

Kitesail Skirmisher

Flying
Whenever Kitesail Skirmisher attacks, another target creature attacking the same player or planeswalker gains flying until end of turn.
Encore {4}{U} ({4}{U}, 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.)

Chart a Course

Draw two cards. Then discard a card unless you attacked this turn.

Dire Fleet Poisoner

Flash
Deathtouch
When Dire Fleet Poisoner enters, target attacking Pirate you control gets +1/+1 and gains deathtouch until end of turn.

Jace, Memory Adept

+1: Draw a card. Target player mills a card.
0: Target player mills ten cards.
−7: Any number of target players each draw twenty cards.

Curious Obsession

Enchant creature
Enchanted creature gets +1/+1 and has "Whenever this creature deals combat damage to a player, you may draw a card."
At the beginning of your end step, if you didn't attack with a creature this turn, sacrifice Curious Obsession.

Warkite Marauder

Flying
Whenever Warkite Marauder attacks, target creature defending player controls loses all abilities and has base power and toughness 0/1 until end of turn.

Raiders' Wake

Whenever an opponent discards a card, that player loses 2 life.
Raid — At the beginning of your end step, if you attacked this turn, target opponent discards a card.

Ghost of Ramirez DePietro

Ghost of Ramirez DePietro can't be blocked by creatures with toughness 3 or greater.
Whenever Ghost of Ramirez DePietro deals combat damage to a player, choose up to one target card in a graveyard that was discarded or put there from a library this turn. Put that card into its owner's hand.
Partner (You can have two commanders if both have partner.)

Deadeye Brawler

Deathtouch
Ascend (If you control ten or more permanents, you get the city's blessing for the rest of the game.)
Whenever Deadeye Brawler deals combat damage to a player, if you have the city's blessing, draw a card.

Brineborn Cutthroat

Flash (You may cast this spell any time you could cast an instant.)
Whenever you cast a spell during an opponent's turn, put a +1/+1 counter on this creature.

Siren Stormtamer

Flying
{U}, Sacrifice Siren Stormtamer: Counter target spell or ability that targets you or a creature you control.

Deadeye Tracker

{1}{B}, {T}: Exile two target cards from an opponent's graveyard. Deadeye Tracker explores. (Reveal the top card of your library. Put that card into your hand if it's a land. Otherwise, put a +1/+1 counter on this creature, then put the card back or put it into your graveyard.)

Heartless Pillage

Target opponent discards two cards.
Raid — If you attacked this turn, create a Treasure token. (It's an artifact with "{T}, Sacrifice this artifact: Add one mana of any color.")

Island

March of the Drowned

Choose one —
• Return target creature card from your graveyard to your hand.
• Return two target Pirate cards from your graveyard to your hand.

Snow-Covered Swamp

Departed Deckhand

When Departed Deckhand becomes the target of a spell, sacrifice it.
Departed Deckhand can't be blocked except by Spirits.
{3}{U}: Another target creature you control can't be blocked this turn except by Spirits.

Corsair Captain

When this creature enters, create a Treasure token. (It's an artifact with "{T}, Sacrifice this token: Add one mana of any color.")
Other Pirates you control get +1/+1.

Depths of Desire

Return target creature to its owner's hand. Create a Treasure token. (It's an artifact with "{T}, Sacrifice this artifact: Add one mana of any color.")

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.