Discreet Retreat

Enchant land
Enchanted land has "{T}: Add two mana of any one color. Spend this mana only to cast outlaw spells or activate abilities of outlaw sources." (Assassins, Mercenaries, Pirates, Rogues, and Warlocks are outlaws.)
Whenever you cast your first outlaw spell each turn, you draw a card and you lose 1 life.

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.

Captain Lannery Storm

Haste
Whenever Captain Lannery Storm attacks, create a Treasure token. (It's an artifact with "{T}, Sacrifice this artifact: Add one mana of any color.")
Whenever you sacrifice a Treasure, Captain Lannery Storm gets +1/+0 until end of turn.

Dire Fleet Neckbreaker

Dire Fleet Ravager

Menace, deathtouch
When Dire Fleet Ravager enters, each player loses a third of their life, rounded up.

Shoot the Sheriff

Destroy target non-outlaw creature. (Assassins, Mercenaries, Pirates, Rogues, and Warlocks are outlaws. Everyone else is fair game.)

Breeches, Brazen Plunderer

Menace
Whenever one or more Pirates you control deal damage to your opponents, exile the top card of each of those opponents' libraries. You may play those cards this turn, and you may spend mana as though it were mana of any color to cast those spells.
Partner (You can have two commanders if both have partner.)

Captivating Crew

{3}{R}: Gain control of target creature an opponent controls until end of turn. Untap that creature. It gains haste until end of turn. 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.)

Glint-Horn Buccaneer

Haste
Whenever you discard a card, Glint-Horn Buccaneer deals 1 damage to each opponent.
{1}{R}, Discard a card: Draw a card. Activate only if Glint-Horn Buccaneer is attacking.

Coercive Recruiter

Whenever Coercive Recruiter or another Pirate you control enters, gain control of target creature until end of turn. Untap that creature. Until end of turn, it gains haste and becomes a Pirate in addition to its other types.

The Master, Multiplied

Myriad
The "legend rule" doesn't apply to creature tokens you control.
Triggered abilities you control can't cause you to sacrifice or exile creature tokens you control.

Laughing Jasper Flint

Creatures you control but don't own are Mercenaries in addition to their other types.
At the beginning of your upkeep, exile the top X cards of target opponent's library, where X is the number of outlaws you control. Until end of turn, you may cast spells from among those cards, and mana of any type can be spent to cast those spells.

Fathom Fleet Captain

Menace
Whenever Fathom Fleet Captain attacks, if you control another nontoken Pirate, you may pay {2}. If you do, create a 2/2 black Pirate creature token with menace.

Kellogg, Dangerous Mind

First strike, haste
Whenever Kellogg, Dangerous Mind attacks, create a Treasure token.
Sacrifice five Treasures: Gain control of target creature for as long as you control Kellogg. Activate only as a sorcery.

Pitiless Plunderer

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

Daring Piracy

At the beginning of combat on your turn, create a 1/1 red Pirate creature token with menace and haste. Exile it at the beginning of the next end step.

Ruin Raider

Raid — At the beginning of your end step, if you attacked this turn, reveal the top card of your library and put that card into your hand. You lose life equal to the card's mana value.

At Knifepoint

During your turn, outlaws you control have first strike. (Assassins, Mercenaries, Pirates, Rogues, and Warlocks are outlaws.)
Whenever you commit a crime, create a 1/1 red Mercenary creature token with "{T}: Target creature you control gets +1/+0 until end of turn. Activate only as a sorcery." This ability triggers only once each turn.

Port Razer

Whenever Port Razer deals combat damage to a player, untap each creature you control. After this phase, there is an additional combat phase.
Port Razer can't attack a player it has already attacked this turn.