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An Emigrant’s Tale: The Ballad Of The Irish Don Juan

Don Juan O’Brien left Baltinglass in 1811 as plain old John O’Brien, earning his new moniker in Buenos Aires, not due to disproportionate amorous exploits, but from the city-dwellers propensity to localise everyone’s name, making even an Irishman from Wicklow sound exotic.

Emigration was common in Ireland; some left to find work, some to escape a criminal charge, and some to avoid the terror of deportation to Australia. Many left to escape religious persecution, others to raise an army, hoping to return and free their native land. But O’Brien left Ireland at the age of twenty-five to plough a different furrow.

He was born into a family of farmers and shopkeepers, relatively well-off for Catholics who had to endure the savagery of the Penal Laws. His father passed away when he was just sixteen, bequeathing him some commercial interests as well as a pair of fine horses, but these steeds were to be O’Brien’s downfall: he lost everything to his unbridled passion for racing, forcing him to mortgage his home – and ask his brothers to do likewise – to keep out of the Debtor’s Prison.

O’Brien decided to try his luck in London, where he first heard of the independence struggle in South America. It captured the imagination of his romantic soul. Returning immediately to bid farewell to the remainder of his family, he secured passage on a Portuguese vessel bound for Rio de Janeiro, his friends providing him with letters of introduction.

Standing on the deck, as his ship cut through the large waves of the open Atlantic seas, with his dreams of opening a merchant house in Buenos Aires, O’Brien was entitled to feel a certain amount of nervous optimism about his future, but his fortunes were about to change once again.

The ship had an uneventful journey until it was dashed on rocks around the island of Fernando Po, off the coast of West Africa. Only O’Brien and a handful of crew survived the wreck. Stricken with fever, his luggage turned to flotsam by the ocean, he made his way, on foot, through the jungle. It was two days before he found a populated cove and vital medical assistance.

After recuperating, he talked his way on to an English packet-ship, and was able to resume his journey to Brazil. Amongst his fellow passengers were a Quaker couple and their young daughter, Rebecca.

O’Brien fell deeply in love with the lass, who was besotted with his roguish charms and tales of adventure. Sick of the subterfuge required for their relationship to flourish, O’Brien approached Rebecca’s father and made his intentions clear: he wished to marry her and sought the Quaker’s approval.

A few days later, after some pressure was exerted on the ship’s captain, O’Brien was forcibly disembarked onto a passing Brazilian ship; Rebecca’s father refusing to countenance his continued presence.

Heartbroken, but in one piece, O’Brien eventually made it to Rio de Janeiro and set about tracking down some of his contacts. A job had been promised, through friends, by a retired English general, which could provide him with the means to earn his passage to Buenos Aires and set himself up in business. However, bad luck had not yet run its course for the Irishman as the general had passed away three months previously.

His relentless determination and indefatigable spirit saw him through and he was able to secure a loan, allowing him to continue to Buenos Aires and begin fulfilling his dream of opening a merchant house. But, like many wide-eyed Europeans in South America, he was swindled early on and forced to seek work in the Army. He enlisted in the newly-formed Mounted Grenadiers and was made a 2nd Lieutenant, soon seeing action during the siege of Montevideo, gaining promotion to Sergeant Major during the victory.

He was rewarded with a much-coveted place in the honour guard to the general who led the assault. An easy life lay ahead for O’Brien as this prestigious post would clear a path for rapid promotion. But, by 1816 he was disenchanted with the general’s politicking and resigned, making his way to Mendoza to join up with his old commander, San Martín.

San Martín remembered O’Brien as a promising young officer. His service record was impeccable, and his instincts in having misgivings about his last post were commendable. It was time to get the measure of this man. San Martín gave him the difficult task of defending the Portillo Pass, giving him command of twenty-five men.

There O’Brien was faced with the probing sorties of the Spanish raiding parties, and it was essential to defend these incursions resolutely to prevent the enemy returning with valuable information regarding the size and readiness of the Argentine forces. But O’Brien and his men faced a greater enemy: the Andean winter.

After six gruelling months, bedding down in the rocks and the snow, O’Brien returned with just eleven of his men. As a reward for the completion of his mission, and the capture of a Spanish Colonel, O’Brien was made Aide-de-Camp to San Martín, a great honour for the young foreign officer.

His adventures didn’t end there, though.

About David Gaughran

David lives in Dublin, where it rains every day and conversation is a sport. He writes historical adventures and has helped thousands of authors to self-publish through his workshops, books, and this here blog.


16 thoughts on “An Emigrant’s Tale: The Ballad Of The Irish Don Juan

  1. Quakers… strange that I relate to that little piece slightly (my teen years were spent attending Quaker Meetings on Sundays). I can see why the austere Quacker man wouldn’t want such a rogue charming his daughter. Thankfully Quackers aren’t nearly that bad any more.

    This tidbit goes to show how some people can really have quite a tale to tell. :}

    Posted by Cathryn Leigh | October 3, 2011, 9:10 pm
  2. A most gratifying first post, Dave!

    But a small query (get used to it – there will be many!):

    “The ship had an uneventful journey until it was dashed on rocks around the island of Fernando Po, off the coast of East Africa.”

    Presuming you meant *West* Africa? But where exactly is the Fernando Po in question? The only island by that name I am familiar with is way south and east near Equatorial Guinea, in completely the opposite direction from Brazil.

    I can understand the ship holding the African coast past Dakar before going crossing the Atlantic, but not why it would ever be this far east?

    Posted by Mark Williams International | October 3, 2011, 11:52 pm
    • Hi Mark,

      Thanks for paying a visit!

      Yes, I meant West Africa and thanks for catching that (I’ve edited the post to hide my shame). The island is the one you are thinking of – now known as Bioko. As to why the boat was that far south when it seems more logical to make the Atlantic crossing further north, it probably has something to do with the trade winds which – I believe – blow northwesterly from there (but I could easily be wrong). Also, the storm may have blown them somewhat off course. Finally, it’s possible is that the ship was calling in at several ports along the way which wouldn’t have been uncommon.


      Posted by davidgaughran | October 3, 2011, 11:59 pm
    • I just checked, and Fernando Po is reasonably close to Sao Tome and Principe which was a Portuguese colony. They could have been stopping there to get provisions before the crossing, take on water, collect mail for Rio, anything. It’s plausible at least.

      Posted by davidgaughran | October 4, 2011, 12:08 am
      • My first thought was maybe this was an old name for an island off Guinea Bissau, which would make more sense from a travel perspective. From my research on the possibility of African reaching South America it seems this tiny Portuguese colony would have made an ideal stocking point for any Portuguese ships bound for Brazil.

        I wonder alternatively if this was a slave ship of some sort? This was the tail end of the trade, and Britain was in theory imposing its own abolition legislation (1807) on other countries, but the British were too preoccupied with European problems to prevent entrepreneurial ship-owners taking advantage

        The distance in the “wrong” direction heading east is just too great to justify unless there was some major commercial benefit.

        Posted by Mark Williams International | October 4, 2011, 12:35 am
      • It’s entirely possible that an “enterprising” captain would choose to load up his boat with all sorts of “cargo” once he was away from the watchful eyes of the owner.

        I think trade winds are also a possibility. If they blow from the southeast (which I think they do around there), then the captain would have to travel a good bit south to catch the right wind to keep the crossing as short as possible.

        Of course, the captain could have been doing all of the above.

        Posted by davidgaughran | October 4, 2011, 12:42 am
  3. History is fascinating, isn’t it? I haven’t read much about South America myself, except David McCullough’s book on the Panama Canal and O. Henry’s stories. Henry spent time in South America after fleeing the United States to escape embezzlement charges, and he wrote quite a lot of stories set there – some serious, but mostly hilarious satire on the continent’s frequent revolutions. Of course that was nearly a century after the time period you’re dealing with here. But I can’t help wondering now if Henry had O’Brien or someone like him in mind when he wrote the spoof “A Ruler of Men” (http://www.literaturecollection.com/a/o_henry/120/).

    Posted by Elisabeth Grace Foley | October 4, 2011, 1:06 am
    • I’m not familiar with “A Ruler of Men”; I’ve only read a little O Henry. I keep meaning to pick up Cabbages & Kings, so thank you for reminding me.

      I think it was Honduras he was holed up in though. I’ve outlined a book set in 1900s Honduras and I’m sure I came across references to him. And as is often the case with Latin America, the truth is stranger than the fiction. This was the time of gunboat diplomacy, banana companies, and rapid growth in the power and influence of the US – a fascinating period. Scores of mercenaries made their names in Central America, often fighting at the behest of one or other of the banana companies. Most of the revolutions sailed out of New Orleans, which was a hotbed of disaffected exiles. It was also the time of the gunning down of the police chief on the steps of his own home, the lynching of suspected Italian mobsters, legalized prostitution where all the brothels were owned by politicians, and the institution of the first national color blindness test, which saw a lot of railroad drivers lose their jobs.

      I’m looking forward to writing it…

      Posted by davidgaughran | October 4, 2011, 2:08 am
  4. The entire story will be intriguing and worth publication when you have it all done. My publisher, All Things That Matter Press, an independent press in Maine, is worth checking out unless you already have one lined up.

    Jean Rodenbough, a new Twitter follower and author of Rachel’s Children: Surviving the Second World War, published by ATTMP.

    Posted by Jean Rodenbough | October 20, 2011, 4:30 am
    • Hi Jean,

      Thank you very much. He did lead an interesting life and there are much more adventures to come. Part of his story is in a historical novel that I will be self-publishing in December, but I had to cut a lot out. I might consider a short narrative non-fiction account of his life, or perhaps include it in a larger book. Still toying with a few different ideas. Thanks for the tip.


      Posted by davidgaughran | October 20, 2011, 11:55 am
      • My name is Jennifer O’Brien from Peru but now living in the United States. I am looking for more info on my great, great, great grandfather general john O’Brien. How can I get access to the remainder of this amazing story. Thank you so much!!!

        Posted by Jennifer O'brien | May 6, 2014, 11:14 am
      • How exciting! I’ll email you shortly…

        Posted by davidgaughran | May 6, 2014, 11:34 am


  1. Pingback: Rip-Offs, Terrible Advice & Zombie Memes | David Gaughran - October 5, 2011

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