Scrooge almost lost his fortune because he could not produce a single heirloom. He also accused Scrooge of not being a true Scot. Scrooge and his nephews managed to defeat him after staging a mock Battle of Culloden.
In the DuckTales episode "Down and Out in Duckburg", a character named Fritter O'Way with the same background took over Scrooge's fortune until Scrooge recovered the cargo sunk with Seafoam's ship, the Golden Goose.
His great-great-grandfather, Swindle McSue, is the man whose case of horseradish Seafoam McDuck agreed to transport in 1776. Because of that incident Scrooge almost lost his fortune.
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