42nd out of 81 books — 34 voters
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Obadiah the Bold
When Obadiah receives a new spy glass, he dreams of becoming a fearless pirate, but with the help of a prank played by his brothers and sisters and a special present from his father, Obadiah learns the true meaning of bravery. Full-color illustrations.
Paperback, 37 pages
Published May 1st 2004 by Beautiful Feet Books
(first published 1965)
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So a little Quaker boy wants to grow up to become a pirate... What's a family to do? A really interesting story - I haven't come across one quite like it. Kinda strange to read "thee" and "thou" but ultimately fun.
Obadiah's back, and dreaming of becoming the first "Friendly" pirate EVAR. His older brothers tease him to the point of sulking by playing pirate; tearful in his father's arms, Obadiah discovers that the ancestor for whom he was named is far braver than any pirate: he rounded the Horn several times and brought all his crew home safely every voyage.