Kitesail Freebooter

Flying
When Kitesail Freebooter enters the battlefield, target opponent reveals their hand. You choose a noncreature, nonland card from it. Exile that card until Kitesail Freebooter leaves the battlefield.

Spyglass Siren

Flying
When Spyglass Siren enters the battlefield, create a Map token. (It's an artifact with "{1}, {T}, Sacrifice this artifact: Target creature you control explores. Activate only as a sorcery.")

Slippery Scoundrel

Ascend (If you control ten or more permanents, you get the city's blessing for the rest of the game.)
As long as you have the city's blessing, Slippery Scoundrel has hexproof and can't be blocked.

Zephyr Singer

Convoke (Your creatures can help cast this spell. Each creature you tap while casting this spell pays for {1} or one mana of that creature's color.)
Flying, vigilance
When Zephyr Singer enters the battlefield, put a flying counter on each creature that convoked it.

Shipwreck Looter

Raid — When Shipwreck Looter enters the battlefield, if you attacked this turn, you may draw a card. If you do, discard 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.)

Azure Fleet Admiral

When Azure Fleet Admiral enters the battlefield, you become the monarch.
Azure Fleet Admiral can't be blocked by creatures the monarch controls.

Dreamcaller Siren

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

Sailor of Means

When Sailor of Means enters the battlefield, create a Treasure token. (It's an artifact with "{T}, Sacrifice this artifact: Add one mana of any color.")

Pirated Copy

You may have Pirated Copy enter the battlefield as a copy of any creature on the battlefield, except it's a Pirate in addition to its other types and it has "Whenever this creature or another creature with the same name deals combat damage to a player, you draw a card."

Forerunner of the Coalition

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

Crafty Cutpurse

Flash
When Crafty Cutpurse enters the battlefield, each token that would be created under an opponent's control this turn is created under your control instead.

Staunch Crewmate

When Staunch Crewmate enters the battlefield, look at the top four cards of your library. You may reveal an artifact or Pirate card from among them and put it into your hand. Put the rest on the bottom of your library in a random order.

Siren Lookout

Flying
When Siren Lookout enters the battlefield, it 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.)

Greedy Freebooter

When Greedy Freebooter dies, scry 1 and create a Treasure token. (To scry 1, look at the top card of your library. You may put that card on the bottom. A Treasure token is an artifact with "{T}, Sacrifice this artifact: Add one mana of any color.")

Grasping Scoundrel

Grasping Scoundrel gets +1/+0 as long as it's attacking.

Kitesail Corsair

Kitesail Corsair has flying as long as it's attacking.

Storm Fleet Negotiator

Flying
Parley — Whenever Storm Fleet Negotiator attacks, each player reveals the top card of their library. For each nonland card revealed this way, you create a Map token. Then each player draws a card. (A Map token is an artifact with "{1}, {T}, Sacrifice this artifact: Target creature you control explores. Activate only as a sorcery.")

Francisco, Fowl Marauder

Flying
Francisco, Fowl Marauder can't block.
Whenever one or more Pirates you control deal damage to a player, Francisco explores.
Partner (You can have two commanders if both have partner.)

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.)

Siren Stormtamer

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

Ramirez DePietro, Pillager

When Ramirez DePietro, Pillager enters the battlefield, you lose 2 life and create two Treasure tokens.
Whenever one or more Pirates you control deal combat damage to a player, exile the top card of that player's library. You may cast that card for as long as it remains exiled.

Kitesail Larcenist

Flying, ward {1}
When Kitesail Larcenist enters the battlefield, for each player, choose up to one other target artifact or creature that player controls. For as long as Kitesail Larcenist remains on the battlefield, the chosen permanents become Treasure artifacts with "{T}, Sacrifice this artifact: Add one mana of any color" and lose all other abilities.

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.

Malcolm, Alluring Scoundrel

Flash
Flying
Whenever Malcolm, Alluring Scoundrel deals combat damage to a player, put a chorus counter on it. Draw a card, then discard a card. If there are four or more chorus counters on Malcolm, you may cast the discarded card without paying its mana cost.

Daring Saboteur

{2}{U}: Daring Saboteur can't be blocked this turn.
Whenever Daring Saboteur deals combat damage to a player, you may draw a card. If you do, discard a card.

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.

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.)

Merchant Raiders

Whenever Merchant Raiders or another Pirate enters the battlefield under your control, tap up to one target creature. That creature doesn't untap during its controller's untap step for as long as you control Merchant Raiders.

Corsair Captain

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

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.

Malcolm, Keen-Eyed Navigator

Flying
Whenever one or more Pirates you control deal damage to your opponents, you create a Treasure token for each opponent dealt damage. (It's an artifact with "{T}, Sacrifice this artifact: Add one mana of any color.")
Partner (You can have two commanders if both have partner.)

Hostage Taker

When Hostage Taker enters the battlefield, exile another target creature or artifact until Hostage Taker leaves the battlefield. You may cast that card for as long as it remains exiled, and mana of any type can be spent to cast that spell.

Waylaying Pirates

When Waylaying Pirates enters the battlefield, if you control an artifact, tap target artifact or creature an opponent controls and put a stun counter on it. (If a permanent with a stun counter would become untapped, remove one from it instead.)

Spectral Sailor

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