Madison was a pirate Captain who first appears in Return to Monkey Island.
She was a young, hip replacement for the old fashioned Pirate Leaders who were in charge on Mêlée Island before. Though all three of the new pirate leaders were captains, Madison seemed to be in command of Lila and Trent.
She was well known and became infamous, being remembered for her adventures by younger generations not born yet. She would appear on collectible trading cards, and according to Boybrush Threepwood, her plunder stats were amazing.
While acting as pirate leader, and in charge of Madison Enterprises, her changes led to the closure of many local businesses including the Mêlée Island Store. She also successfully pushed to shut down the shipyard. Due to Lila's dark magic, voodoo was going out of fashion too, and so business at The International House of Mojo suffered.
Some blamed Madison's presence for bringing a 'bad element' to town, which was a major cause of the businesses going under.
The search for the Secret of Monkey Island[]
Guybrush Threepwood approached her in the Scumm Bar hoping she could finance his expedition to hunt for the true Secret of Monkey Island.
She refused, not believing the secret was even real, but soon after it was discovered that she wished to find it herself. All she needed was the map that LeChuck had. She hired Murray to spy on him.
She teamed up with Threepwood, intending to use his access to LeChuck's ship to get what she needed, then double cross him.
Her plan worked and soon LeChuck was after her.
They fought, and when the battle came to a stalemate, she and LeChuck joined forces, once again intending to betray one another.
Once they had the treasure chest containing the secret, LeChuck took them below the giant monkey head to unlock it in a ritual.
However, Madison was betrayed and killed by Captain Lila, who wanted the secret for herself.