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 this Aura.

Skyship Plunderer

Flying
Whenever this creature deals combat damage to a player, for each kind of counter on target permanent or player, give that permanent or player another counter of that kind.

Storm Fleet Swashbuckler

Ascend (If you control ten or more permanents, you get the city's blessing for the rest of the game.)
This creature has double strike as long as you have the city's blessing.

Siren Lookout

Flying
When this creature enters, 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.)

Burdened Aerialist

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

Grasping Scoundrel

This creature gets +1/+0 as long as it's attacking.

Spectral Sailor

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

Buccaneer's Bravado

Choose one —
• Target creature gets +1/+1 and gains first strike until end of turn.
• Target Pirate gets +1/+1 and gains double strike until end of turn.

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.

Island

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.

Swaggering Corsair

Raid — This creature enters with a +1/+1 counter on it if you attacked this turn.

Warkite Marauder

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

Deadeye Tormentor

Raid — When this creature enters, if you attacked this turn, target opponent discards a card.

Stoneforge Masterwork

Equipped creature gets +1/+1 for each other creature you control that shares a creature type with it.
Equip {2}

Changeling Outcast

Changeling (This card is every creature type.)
This creature can't block and can't be blocked.

Kitesail Corsair

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

Brazen Buccaneers

Haste
When this creature enters, 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.)

Mountain

Prosperous Pirates

When this creature enters, create two Treasure tokens. (They're artifacts with "{T}, Sacrifice this token: Add one mana of any color.")

Fathom Fleet Cutthroat

When this creature enters, destroy target creature an opponent controls that was dealt damage this turn.

Sailor of Means

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

Pirate's Cutlass

When this Equipment enters, attach it to target Pirate you control.
Equipped creature gets +2/+1.
Equip {2} ({2}: Attach to target creature you control. Equip only as a sorcery.)

Hostage Taker

When this creature enters, exile another target creature or artifact until this creature 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.

Brazen Freebooter

Departed Deckhand

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

Daring Buccaneer

As an additional cost to cast this spell, reveal a Pirate card from your hand or pay {2}.

Dire Fleet Interloper

Menace
When this creature enters, 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.)

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, this creature has hexproof and can't be blocked.

Impulsive Pilferer

When this creature dies, create a Treasure token. (It's an artifact with "{T}, Sacrifice this token: Add one mana of any color.")
Encore {3}{R} ({3}{R}, 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.)

Deadeye Rig-Hauler

Raid — When this creature enters, if you attacked this turn, you may return target creature to its owner's hand.