Roberto Confresi

  • Piracy
  • 2 mins

By Crusader1307

Born into a wealthy (Spanish) Family, Confresi lived as a boy and teenager in Puerto Rico (Spanish Colony). Due to the many Wars (and a lagging Economy both there and in Spain) – The Confresi Family were “Poor Nobles”. Wanting to make his own way, Roberto went to sea. Why he chose Piracy over Commerce is unclear (perhaps it was to help his family – or to keep himself from being poor). His raiding is documented at around 1823 (around the time of the death of the famed Jean Lafitte). He targeted The West Indies with great success. Preferring smaller Sloop-Class ships, he was said to have had at one time as many as 20 ships in his “Fleet”. He was sought (wanted) by 6 Nations at one time. He evaded capture due to his knowledge of the inlets and general Coastline of the Isle of Puerto Rico.

Never an “active Shooter”, Confresi preferred to outrun his pursuers. It is documented that he did engage at least 2 American Warships (and escaped both). Another key to Confresi's success was his crews. Recruited locally and always well paid, their was no chance of betrayal. He was known for his “larger than life personality” and was surprisingly well liked – for a Pirate. He had an extensive “civilian” network of spies and informants working for him (that would take 15 years after his death to fully account and dismantle!). Even though “well though of”, Confresi still was a Pirate and as such, had a simple Code. If they captured a ship, the crew was given the chance to join – or die. Although Confresi never “confessed” to murder, he was credited with around 300 deaths (related to his Piracy). His Flagship The “Anne” finally was outmatched by a Dutch Fleet sent specifically to take him either “in or down”.


Confresi attempted to bride his way out with his impressive “stash” of treasure, but to no avail. Convicted by a Military Tribunal, he was hung in 1825. His legend is still alive in Puerto Rico where he is looked upon as a Robin Hood figure. And as legend dictates, MUCH of his treasure is still hidden!