Don Andres, the Renegade

Each creature you control but don't own gets +2/+2, has menace and deathtouch, and is a Pirate in addition to its other types.
Whenever you cast a noncreature spell you don't own, create two tapped Treasure tokens.

Obeka, Splitter of Seconds

Menace
Whenever Obeka, Splitter of Seconds deals combat damage to a player, you get that many additional upkeep steps after this phase.

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.

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.