Regarded as the last successful pirate of the Caribbean during the 19th century's suppression era, the life of Roberto Cofresí has been romanticized in his native Puerto Rico and neighboring nations. Already possessing a reputation as hard to capture in life, the freebooter became a symbol for an archipelago immersed in the political unrest caused by its status as a colony within the struggling Spanish Empire. Under these circumstances, Cofresí was soon characterized as a benign and generous thief. In a similar trend, he was also associated with the Puerto Rican independence movement of the era. During the late 19th and early 20th century, the abundant oral tradition led to a subgenre of folk hero literature which depicted Cofresí as a benevolent force and contradicted the other pirate-related works of the time, including the well known Treasure Island and Peter Pan. A century later, this contrast became the subject of sociological study. Research to uncover the historical figure behind these myths has also been published by authors linked to the Puerto Rican Genealogical Society, which creates a parallel to this narrative.

While in prison, Cofresí claimed to possess at least 4,000 pieces of eight still accessible after the authorities confiscated his ship, mentioning them in an unsuccessful attempt to bribe an officer in exchange for his freedom. This made him one of the few pirates that are implied to have kept a hidden cache, a rare occurrence despite its prominence in popular culture due to their tendency to divide and misspend the earnings, and fueled legends of buried treasures waiting to be found. All sort of objects serve as the subjects of these tales, from magic guitars made of solid gold to chests that are bound to chains that emerge from the sea. This tendency had extended to Hispaniola by the end of the 19th century, with a novel claiming that the island served as the locale of such treasures. During the 20th century, the destination marketing organizations in the region took notice of them and began exploiting the association of certain places and the pirate to attract tourism. Raising his profile during this time period also led to several non-profit homages. Cofresí has since served as the namesake of several sport teams and events, vehicles, companies, alcoholic brands and hotels. Figures such as Alejandro Tapia y Rivera, Luis Lloréns Torres, Rafael Hernández Marín and Juan Emilio Viguié worked to adapt the legends to other mediums, including plays, popular music and films. Cofresí is also the only pirate of the pre-flight era to have a copycat crime in his stead recorded during the 20th century. This happened when his name was employed as an alias during the first act of sky piracy involving an American airline.

An entirely different class of myths was created by those that were directly affected by his actions, be it politically or economically. The first to vilify the pirate and his deeds were the merchants that suffered severe losses during the peak of his career, who described him as nothing more than a tyrant. A mistranslated letter that actually reports the death of a crewmember, but misidentifies it as "Cofresin", may have been the catalyst behind several legends that grant Cofresí a connection to the supernatural. These come in two classes, those that portray him as being nearly impossible to eliminate, employing magic to survive lethal wounds such as being stabbed in the heart or even reincarnating if successfully killed, and those that grant extraordinary powers to his ghost. A variety of reasons are given for these abilities, from a pact with the Devil to the practice of witchcraft or mysticism. Some curses are also associated to his figure, of which at least one is purported to have been fulfilled with the shipwreck of the U.S.S. Grampus. Of these, most concern those that loot the treasures that he left behind and usually conclude with the victim dead or dragged to Davy Jones's locker.

Traits and popular perception As is the case with other pirates, the actual traits of Cofresí became romanticized and entangled in the mythic aura that surrounds his person long ago. Cofresí was known to be bold and risky, to the point that Salvador Brau argues in Historia de Puerto Rico that had he lived during the 18th century, he would have even eclipsed the accomplishments of Miguel Enríquez. Historian Walter Cardona Bonet also supports this notion, noting that he acted with "a lot of courage and bravery", with his leadership being further established by his "charisma [and] intelligence". This particular aspect, has been heavily mystified, with most legends emphasizing his bravery. The Spanish authorities actually recognized this trait, which Pedro Tomas de Córdova notes in his compilation, Memorias, and may have unwittingly help develop a cult of personality around his figure. During his lifetime, the colonial government of Puerto Rico made efforts to portray him as a fierce and violent criminal. His epithet, "The Terror of the Seas", reflects his position as the unopposed "Pirate Lord" of the region during the early 19th century. In the United States, the media did its part by sensationalizing Cofresí's death row confession of having murdered around 400 victims. This had the effect of portraying him as an antithesis to authority in a troubled society. Author Robert Fernández Valledor notes that the legends that follow his life basically emerge from this status as "Puerto Rico's first rebel". As a consequence of the power void following his death, there was a sharp decline in piracy as no other figure could gather the support of the local population in this fashion. This tendency was reflected throughout the Caribbean, where no pirate would be involved in instigating a similar number of homicides until "The Rajah" John Boysie Singh in the 20th century.

Cofresí is said to have possessed a rebellious personality and to have been rather independent, taking decisions under his own criteria. He also appeared to be very keen, to the point of being capable of causing the ridicule of the authorities that pursued him. His nautical savvy and familiarity with naval strategy have been attributed to a privileged education and growing in a harbor town. According to historian Enriquez Ramírez Brau's Cofresí: historia y genealogía de un pirata, 1791-1825, the siblings went to private school in their hometown of Cabo Rojo, where the young Roberto was mentored by Ignacio Venero. This figure is said to have taught him Roman Catholic catechism, literature and arithmetic, among other subjects. The young Cofresí is said to have displayed a particular interest in geography. Living in a coastal municipality, the brothers often came into contact with visiting sailors. They were inspired to become seamen by the tales that they heard from the sailors who visited their town. Cofresí eventually purchased a small boat. His brothers attempted to convince him to quit these ventures, but their requests were ignored. According to popular belief, his first vessel was known as El Mosquito or Relámpago, depending on the account.

Cofresí's physical appearance has been idealized, often being described as athletic, muscular, agile, with masculine traits and of medium height. However, as part this process he has also been differentiated from most contemporary Puerto Ricans, with multiple authors describing him as possessing blue eyes and curly blonde hair. Based on both tradition and the physical appearance of those related to him, historian Ursula Acosta supports this notion, stating that he most likely had blonde or brown hair and light-colored eyes. She also notes that the Ramírez de Arellano lineage also had a heavy Nordic origin. Some accounts incorrectly label him as tanned or mestizo, product of Taíno and Spanish bloodlines. These likely attempted to adapt Cofresí to what is now regarded as the common Puerto Rican ethnicity composed of Spanish, Taíno and African heritage. In 1846, reporter Freeman Hunt introduced several of these elements to his North American public by describing a scene that took place after the pirate's final arrest. He states that the authorities were surprised after finding a "handsome" young man with an "intelligent" and "very amiable" facial expression, who due to a "gentlemanly bearing" would "never have been taken for a murderer or a pirate". Besides emphasizing his brilliance and a "suavity of the Spanish manner", Hunt takes note of a reputation for "daring", "energy" and "celebrity".

Stories have linked him to a host of women, including an account where he serves as the lover of a Cacique's wife, despite the fact that by the 19th century the Taíno's domain had fallen apart. One particular tale names his lover "Ana", after his ship. These contradict historic documents that actually place Cofresí close to Juana throughout his life, offering no further evidence supporting this reputation. However, given the era's cultural approach and customs there is a possibility that he may have had several unrecorded lovers. This interpretation of Cofresí's personality found its way to the angloparlant media during the first half of the 20th century. The September 17, 1939, edition of The Milwaukee Sentinel relays an account in which the pirate crew capture a schooner that had several Spanish women as passengers. According to this story, the captured ship attempted to escape under the cover of darkness. However, the crew of the schooner was unfit to travel under stormy weather and the vessel came close to sinking. The account concludes with Cofresí defying the weather and rescuing the women, but not before charming them with his manners.

Influence in modern culture

Oral tradition Cofresí's life and death have inspired several myths and stories. These included those depicting him as a generous figure, who used to share what he stole with the region's poor population. In these myths he is generally described as a benevolent person, with authors writing about his supposed personality. Others take note of his purported sense of humor. In general, these portray him as a noble gentleman who became a pirate out of necessity or as a generous man, claiming that on one occasion he provided money for the upbringing of a baby girl that he had saved. Others depict a brave man, showing disregard for his life on several occasions. The "generous thief" archetype that is associated with Cofresí was predominant during the 19th century, being promoted by the romanticism present in the work of several prominent authors. Further influenced by an anti-establishment sentiment that arose from the dire conditions of the general population, the poor people quickly identified with these "rebels", "who were simply trying to make justice in an unfair social structure where the poor would always take the worst part". Shortly after his death, the popular songs that described his life painted his actions in a positive light, as "feats" instead of crimes. Another copla testifies how the general public praises his bravery, while labeling the authorities as cowards. However, the merchant class also had its own oral tradition, which portrayed him as a "tyrant" of the seas and celebrates that with him gone the business would be normalized. An example from Guayama claims that the pirates would bait the crews of passing vessels by disembarking at Cayo Caribe and posing as shipwrecked sailors, murdering them after the ships ran aground in the shallows. The Spanish government tried to create a parallel reputation, perpetuating Cofresí as a vile murder and thief. The American government fueled this, describing him as a "famous piratical chief" that ran a "bloodthirsty" leadership.