The Story of the mythical pirate Juan Eduardo De Rivera He was the most infamous pirate ever to sail on the waters of the Great Lakes. From the forecastle of his swift schooner, the Diamante Negro, he would send his marauding band of men to roam and plunder the small fishing villages and trading settlements that dotted the shorelines of Lakes Erie, Huron and Michigan, taking whatever they wanted from whomever they wanted whenever they wanted! De Rivera once plied the waters of the Gulf of Mexico before moving north in 1793 to the lucrative inland seas of the Great Lakes. He decided to leave the southern waters where he had to compete with dozens of other scoundrels for the bounty of the merchant ships that plied the trade routes from Mexico to England or Spain. On the Great Lakes, De Rivera could truly be a swashbuckling buccaneer and go virtually unchallenged. It was an ideal setup. He was tall for a seaman, standing a towering 6'4". He had a ruddy, sun-hardened complexion and a booming voice. He had gone to sea at the young age of 13 as a cabin boy aboard the ship of the feared and infamous Cuban raider, Jose Gasparilla. Although this mythical pirate was reputed to attack anything that moved on the sea, Gasparilla was most famous for his nighttime raids on a prosperous Florida city named Tampa. Under Gasparilla, De Rivera learned the tactics of invading, pillaging and escaping before the cover of night could give way to the first light of morning. It was the perfect training for De Rivera's arrival on the Great Lakes. Although a few passenger schooners sailing from Chicago to Buffalo carried gold-laden prospectors returning from the West, most ships lying the Great Lakes carried no treasure. So De Rivera targeted the settlements and towns along the shores and up the rivers, just like his mentor Gasparilla did to Tampa and other Florida cities. Uncontested, De Rivera ran freely all over the Great Lakes, his coffers becoming ever more swollen with bounty. And just like Gasparilla, De Rivera became increasingly proficient and confident in his ability to successfully descend on increasingly larger settlements where the potential bounty was bigger. The "Invasion of Invasions" It was in June of 1799 that De Rivera executed his most famous raid. It was a pirate invasion like no other ever attempted on the Great Lakes. In fact, it's believed no other raid of such magnitude was ever attempted again. The target was a large settlement named Cleveland, founded in 1796 by Moses Cleaveland. It lay on the south shore of Lake Erie, a peaceful albeit bustling hub of fur trading and commerce built at the mouth of a large winding river they called Cuyahoga. It was to become the largest city in America's heartland ever to be plundered by a band of pirates. To De Rivera, Cleveland represented the ultimate challenge, not to mention a most-handsome payoff since the city was reputed to have many wealthy traders who fed cash-rich banks. But there was even more. Cleveland was noted for its large distilleries. More whiskey was made in Cleveland, on a strip of lakefront land named Whiskey Island, than in De Rivera's hometown of Havana. There was also an abundance of Cleveland nightlife and, yes, stories of it being a city of beautiful women of society. It was, by all measures, more than a pirate could resist! What's more, plundering Cleveland would make even Gasparilla's sorties into Tampa look insignificant. Cleveland would be hailed as the "invasion of pirate invasions." Stories of De Rivera's escapade would surely be told by seafarers around the globe. Such thoughts just further ignited his passion for the invasion with each day of planning. Amazingly, De Rivera's scheme to plunder Cleveland was filled with tactical brilliance! The obvious landing place was up the Cuyahoga River. But, he learned the River was often congested with merchant ships along its riverbanks. Navigation in and escape out could be difficult. There were also reports that many soldiers from Fort Scranton, located just upstream, were always in the pubs and bawdy houses that lined the "Flats" area of the riverfront. So, De Rivera chose to land at a place of easier access, where he could silently sail in directly from the open Lake and escape the same way. From that landing point, his men could easily race to the heart of the city in just a few minutes. Today, that landing area has been dubbed Cleveland's "North Coast Harbor." By far the biggest change De Rivera made in his plan to pillage Cleveland was the timing. Pirates had always struck towns only at night. But De Rivera shelved the safety of raiding only under the cover of darkness for a bold, untested, incursion in broad daylight. The crew of Diamante Negro was skeptical and rejected the plan at first. But, De Rivera persisted and, ultimately, the revolutionary plan was accepted. Cleverly, De Rivera proposed to invade on a Saturday morning, believing the people of Cleveland would have just finished a typical Friday night of overindulgence in fine spirits and night time frivolity. The city would be drowsy at worst and still asleep at best, he convinced his sailors. They would likely go into the City completely unchallenged, he told them. In fact, other than that his men might look and smell a little less inviting than the Cleveland citizenry itself, the pirates would probably blend right in and would go unnoticed for hours. Before anyone would even know the banks were empty, some wagon loads of Cleveland whiskey had been hauled to the lakefront, and some homes of Cleveland's wealthiest were missing their silver, not to mention that more than a few of Cleveland's fair ladies had been defiled, the fleet-hulled Diamante Negro will have set sail for a hide out along the wilderness northern shore of Lake Erie. Yes, thought De Rivera, this would be the invasion that would be spoken of with awe and admiration by pirates everywhere. Juan Eduardo De Rivera at last year's Festival And so it was that Juan Eduardo De Rivera sailed into the North Coast Harbor and recorded the greatest pirate invasion of all time. And even today this legendary pirate lives on in stories often shared on the decks of ships. The End of De Rivera What ultimately happened to De Rivera is mostly a matter of conjecture. It is said that he sailed the Great Lakes for several more years after Cleveland, mostly staying on the Canadian side. One story has it that he and his crew divided up the enormous riches they'd accumulated, scuttled the Diamante Negro one night at the mouth of the Buffalo River and headed east to get lost and live lavishly in the teaming population of New York City. But Canadian historians claim his end came in Amherstburg on the Detroit River in 1809. There, De Rivera rose at dawn to find his Diamante Negro surrounded by four Canadian gunboats allowing no escape route. The crew of Diamante Negro eventually launched a skiff and surrendered to the Canadians. All except De Rivera, that is. It's recorded in one of the gunboat logbooks that De Rivera, standing on the bow of his ship declaring he wouldn't be taken alive, flaunted his last act of defiance by lashing his feet to a Diamante Negro anchor and cut it loose! He disappeared into the water and was not seen again, it is recorded. But as the crew of the Diamante Negro later told the story, no one really knows for sure if the De Rivera didn't cut himself loose from that anchor that morning and reach the shore unnoticed - surely not too great a feat for the greatest mythical pirate ever to sail the Great Lakes.