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.

Back in Town

Return X target outlaw creature cards from your graveyard to the battlefield. (Assassins, Mercenaries, Pirates, Rogues, and Warlocks are outlaws.)

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.

Graywater's Fixer

Each outlaw creature card in your graveyard has encore {X}, where X is its mana value. (Exile it and pay its encore cost: 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.)

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.)

Olivia, Opulent Outlaw

Flying, lifelink
Whenever one or more outlaws you control deal combat damage to a player, create a Treasure token. (Assassins, Mercenaries, Pirates, Rogues, and Warlocks are outlaws.)
{3}, Sacrifice two Treasures: Put two +1/+1 counters on each creature you control. Activate only as a sorcery.

Hellspur Posse Boss

Other outlaws you control have haste. (Assassins, Mercenaries, Pirates, Rogues, and Warlocks are outlaws.)
When this creature enters, create two 1/1 red Mercenary creature tokens with "{T}: Target creature you control gets +1/+0 until end of turn. Activate only as a sorcery."

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.