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.

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.)

Prosperous Pirates

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

Island

Lookout's Dispersal

This spell costs {1} less to cast if you control a Pirate.
Counter target spell unless its controller pays {4}.

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.

Alora, Merry Thief

Whenever you attack, up to one target attacking creature can't be blocked this turn. Return that creature to its owner's hand at the beginning of the next end step.
Choose a Background (You can have a Background as a second commander.)

Corsair Captain

When Corsair Captain enters, 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.

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.

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.

Counterspell

Chart a Course

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

Brainstorm

Draw three cards, then put two cards from your hand on top of your library in any order.

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.

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.

Goldvein Pick

Equipped creature gets +1/+1.
Whenever equipped creature deals combat damage to a player, create a Treasure token. (It's an artifact with "{T}, Sacrifice this artifact: Add one mana of any color.")
Equip {1} ({1}: Attach to target creature you control. Equip only as a sorcery.)

Reflections of Littjara

As Reflections of Littjara enters, choose a creature type.
Whenever you cast a spell of the chosen type, copy that spell. (A copy of a permanent spell becomes a token.)

Sword Coast Sailor

Commander creatures you own have "Whenever this creature attacks a player, if no opponent has more life than that player, this creature can't be blocked this turn."

Sailor of Means

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

Fell Flagship

Pirates you control get +1/+0.
Whenever Fell Flagship deals combat damage to a player, that player discards a card.
Crew 3 (Tap any number of creatures you control with total power 3 or more: This Vehicle becomes an artifact creature until end of turn.)

Mystic Sanctuary

({T}: Add {U}.)
Mystic Sanctuary enters tapped unless you control three or more other Islands.
When Mystic Sanctuary enters untapped, you may put target instant or sorcery card from your graveyard on top of your library.

Prying Blade

Equipped creature gets +1/+0.
Whenever equipped creature deals combat damage to a player, create a Treasure token. (It's an artifact with "{T}, Sacrifice this artifact: Add one mana of any color.")
Equip {2} ({2}: Attach to target creature you control. Equip only as a sorcery.)

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.

Siren Stormtamer

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

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.

Pirate's Cutlass

When Pirate's Cutlass 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.)

Silver Myr

Rishadan Brigand

Flying
When Rishadan Brigand enters, each opponent sacrifices a permanent unless they pay {3}.
Rishadan Brigand can block only creatures with flying.

Castle Vantress

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

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.