Ireland's Cruelest Pirate: The Untold Story (Part 2 of 3)

Part 2 of a 3-part series on the never before revealed alternative history of Ireland's least famous pirate, from the widely ignored paper by Dr. Padraig Finagle, reprinted by kind permission. (If you missed Part 1, it's HERE.

Excerpt from Part 1:

Séamlus O'Toole (c. 1650 - 1694) is the most famous Irish pirate in maritime alternative history. Little is known of his origins beyond a vague reference in a mid-15th century Irish tavern ledger, discovered in university archives at Dublin in 1984. The entry appears to identify his father as being a sailor (name unknown) who skipped out on his reckoning, and his mother a tavern "strumpet" whom he failed to pay for services rendered, thus losing the landlord his cut, and gaining the lady a son.

Begin Part 2:


Drawing of Irish pirate Seamlus O'TooleAccording to maritime folk legends that grew up around him, the only weapon O'Toole ever used was a big ugly blackthorn cudgel, or "shillelagh", from which arose the name by which he is today remembered: Shillelagh O'Toole.  

Seafaring legend hands down an image of a thoroughly depraved, merciless marauder, enamored of his big shillelagh (modern historians have postulated that he suffered from NPD). We are left with a picture of an evil red-haired bandit of the brine who wreaked havoc upon travelers of many nations, abused women, and scuttled perfectly sound ships for fun and profit (when he did not take them outright and give them over to various unprincipled henchmen to toy with), until the fateful day when he met a man "whose shillelagh was bigger than his". Modern-day philosophers see in this a Life Lesson to which certain People in High Places right now would do well to pay heed.


David Neil O’Dowd (c. 1673 - 1755), an Irishman and compatriot of O’Toole is credited with killing him during his attempt to board and take the Scottish freighter Maid O’Cadiz, enroute from Valencia to Dundee with a cargo of oranges for the marmalade industry.

Why O’Toole would have wanted such a cargo remains a matter for speculation, as the benefits of vitamin C in the prevention and cure of scurvy were unknown at the time. Some folklorists who really should get out more think someone may have told him that the orange stuff the Maid carried in her hold was some rare kind of Spanish gold, and the greedy bastard believed it.

There is no historical proof of how death was inflicted. However, maritime folk legend has it that O’Dowd was also possessed of an Irish shillelagh, which was bigger than O’Toole’s, and with which the young sailor "knocked old O’Toole straight into Hell", thereby ending the pirate's legend and launching his own.



Prof. Padraic FinagleABOUT THE AUTHOR:
Padraig Finagle is Ass. Professor of Alternative History and Brewing at the Auxiliary Maritime Institute and Public House of Skibbereen, Ireland. He holds an MBA (Master of Brewing Ales) from Boozer University, Kilkenny Ireland and is a fellow of the Guinness Institute, from which he holds an honorary D.D.T. (Doctor of Delirium Tremens).

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