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.

Kukemssa Pirates

Whenever Kukemssa Pirates attacks and isn't blocked, you may gain control of target artifact defending player controls. If you do, Kukemssa Pirates assigns no combat damage this 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.

Siren's Ruse

Exile target creature you control, then return that card to the battlefield under its owner's control. If a Pirate was exiled this way, draw 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.)

Merchant Raiders

Whenever Merchant Raiders or another Pirate you control enters, 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.

Spectral Sailor

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

Castle Vantress

Castle Vantress enters tapped unless you control an Island.
{T}: Add {U}.
{2}{U}{U}, {T}: Scry 2.

Island

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.

Spell Swindle

Counter target spell. Create X Treasure tokens, where X is that spell's mana value. (They're artifacts with "{T}, Sacrifice this artifact: Add one mana of any color.")

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.

The Indomitable

Trample
Whenever a creature you control deals combat damage to a player, draw a card.
Crew 3
You may cast The Indomitable from your graveyard as long as you control three or more tapped Pirates and/or Vehicles.

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.

Double Down

Whenever you cast an outlaw spell, copy that spell. (Assassins, Mercenaries, Pirates, Rogues, and Warlocks are outlaws. Copies of permanent spells become tokens.)

Crafty Cutpurse

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

War Tax

{X}{U}: This turn, creatures can't attack unless their controller pays {X} for each attacking creature they control.

Azure Fleet Admiral

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

Siren Stormtamer

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

Timestream Navigator

Ascend (If you control ten or more permanents, you get the city's blessing for the rest of the game.)
{2}{U}{U}, {T}, Put Timestream Navigator on the bottom of its owner's library: Take an extra turn after this one. Activate only if you have the city's blessing.

Subterranean Schooner

Whenever Subterranean Schooner attacks, target creature that crewed it this turn 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 that creature, then put the card back or put it into your graveyard.)
Crew 1

Pirated Copy

You may have Pirated Copy enter 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."

Kitesail Larcenist

Flying, ward {1}
When Kitesail Larcenist enters, 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.

Hornswoggle

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

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, put a flying counter on each creature that convoked it.

Staunch Crewmate

When Staunch Crewmate enters, 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.

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.

Admiral's Order

Raid — If you attacked this turn, you may pay {U} rather than pay this spell's mana cost.
Counter target spell.

Thriving Isle

Thriving Isle enters tapped. As it enters, choose a color other than blue.
{T}: Add {U} or one mana of the chosen color.

Scry 1. (Look at the top card of your library. You may put that card on the bottom.)
Draw a card.

Amphin Mutineer

When Amphin Mutineer enters, exile up to one target non-Salamander creature. That creature's controller creates a 4/3 blue Salamander Warrior creature token.
Encore {4}{U}{U} ({4}{U}{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.)

Coastal Piracy

Whenever a creature you control deals combat damage to an opponent, you may draw a card.

Pirate Hat

Equipped creature gets +1/+1 and has "Whenever this creature attacks, draw a card, then discard a card."
Equip Pirate {1}
Equip {2} ({2}: Attach to target creature you control. Equip only as a sorcery.)

Sea Gate

Sea Gate enters tapped.
As Sea Gate enters, choose a color other than blue.
{T}: Add {U} or one mana of the chosen color.

Corsairs of Umbar

{2}{U}: Target Goblin, Orc, or Pirate can't be blocked this turn.
Whenever Corsairs of Umbar deals combat damage to a player, amass Orcs 3. (Put three +1/+1 counters on an Army you control. It's also an Orc. If you don't control an Army, create a 0/0 black Orc Army creature token first.)

Lonely Sandbar

Lonely Sandbar enters tapped.
{T}: Add {U}.
Cycling {U} ({U}, Discard this card: Draw a card.)