Simón Bolívar was born in Caracas, Venezuela on 24 July 1783, into one of the wealthiest families in the Spanish Americas. Orphaned by the age of nine, he nevertheless grew up amid the comforts of the colonial elite, his family’s fortune affording him an education in both Venezuela and Spain. By his early twenties, however, a strong desire for a South America free from the Spanish crown had begun to manifest within him.Venezuela at the time was a province of the larger Viceroyalty of New Granada, which also encompassed present-day Colombia, Panama and Ecuador. Spain governed its American territories through a strict hierarchy: the crown, advised by the Council of the Indies, appointed viceroys for each territory. Although the colonies were officially considered provinces of equal stature to the Iberian homeland, in reality the system extracted the wealth and resources of Spanish America away from the continent, Venezuela’s major export at the time being cacao. The Bolívar family itself had amassed its wealth within this system through its extensive mines and plantations.From 1803 to 1805, the young aristocrat undertook a grand tour of Europe, spending time in Spain, the newly Napoleonic France and finally Italy. Along the way, Bolívar immersed himself in Enlightenment thought — reading figures such as Jean-Jacques Rousseau and contemplating the recent French and American revolutions. His intellectual and political awakening culminated in a symbolic moment on Rome’s Monte Sacro in 1805, where he would vow to liberate his homeland from Spanish rule.True to his word he returned to Venezuela in 1807. In October of that same year Napoleon’s armies invaded Spain, igniting the Peninsular War (1807–1814) — a prolonged and destabilising conflict that gravely weakened Spain’s grip on its American territories. By 1808, Napoleon had forced King Ferdinand VII to abdicate and installed his brother Joseph on the Spanish throne. For the colonies, the upheaval posed an existential question: should they continue to recognise the authority of the deposed Ferdinand, whose allies were now waging a war to liberate Spain, or cut loose and establish self-governance?In the early 1810s, Venezuela grappled with the colonial crisis, attempting twice to establish an independent republic. Bolívar emerged as a key figure as both diplomat and general, and in 1813 led the Campaña Admirable (Admirable Campaign), a string of military victories that briefly restored the republic after its first collapse. But the gains proved short-lived. By 1815, royalist troops had once again seized Caracas, and Bolívar, now on the back foot, was forced into exile. He sailed to Jamaica, hoping to win the attention, and possibly the cooperation, of the British empire.In Jamaica, he wrote what became known as ‘La carta de Jamaica’ (1815; ‘The Jamaica Letter’),1 possibly in response to an earlier letter from an English merchant whose sympathies to the cause could help in gaining Britain's support. In the letter, Bolívar paints a bleak picture of Latin America’s future under continued Spanish rule — as a land reduced to ‘Fields for the cultivation of indigo, grain, coffee, sugar cane, cacao and cotton…the bowels of the earth for excavating gold that will never satisfy the lust of that greedy nation’.2In the letter, Bolívar affirms his vision of a fully independent Spanish America, but he also identifies a fundamental obstacle, namely, that centuries of colonial rule had left the new nations ill-prepared for self-governance.3 ‘The Americans have made their debut on the world stage suddenly and without prior knowledge or, to make matters worse, experience in public affairs’.4 A central theme of the letter is Bolívar’s belief that Spanish America would not follow a uniform path to independence, comparing the continent’s struggles to the break-up of the Western Roman Empire ‘when each breakaway province formed a political system suitable to its interests and situation’.5While he greatly admired the republican ideals of the United States he came to doubt their viability in Spanish America, with the repeated collapse of Venezuela’s early republics only reinforcing his scepticism. The idea that independence might best be secured not through republicanism, but through strong, centralised leadership is implicit in the Jamaica Letter, where he writes: ‘Although I aspire to a perfect government for my country, I cannot persuade myself that the New World is ready at this time to be governed by a grand republic.’6Bolivar’s Jamaica Letter, then, exposes a fundamental paradox: although he championed the cause of independence and professed republican ideals, he was convinced that the realities of postcolonial South America demanded strong, centralised — even authoritarian — leadership to secure lasting freedom and stability. One of the most direct expressions of these ideas came in the form of the 1826 Bolivian constitution, drafted by Bolívar himself shortly after the founding of the nation that now bore his name. Here, Bolívar introduced the office of a lifetime presidency — a role that not only concentrated executive power, but also gave its holder the right to appoint a successor.7 While this constitution was short-lived, with Bolivia soon succumbing to in-fighting, arguably, it laid the groundwork for the emergence of Caudillismo in Latin American politics.Caudillismo refers to a Latin American political tradition in which charismatic strongmen (often military leaders) rise to power through personal authority rather than democratic process. The echoes of Bolívar’s political model can be felt in the presidency of Hugo Chávez, elected in Venezuela in 1999. Often labelled a Caudillo by his critics, Chávez launched the so-called ‘Bolivarian Revolution’, a program of nationalisation, wealth redistribution, and expansive social policy, grounded in his government’s interpretation of Bolívar’s legacy. Yet throughout his presidency, authoritarian tendencies intensified, evidenced by an increasing centralisation of power, the entrenchment of military influence in government, and constitutional reforms enabling indefinite re-election.8The Jamaica Letter offers a crucial window into the ambitions — and contradictions — of one of South America’s most enduring figures. Bolívar’s vision was rooted in the ideal of freedom, yet constrained by the Realpolitik (that is, politics as dictated by unstable ground realities over ideological purity) of a continent in turmoil. In the years that followed, Bolívar would return to his role as General and lead successful independence campaigns in Venezuela, Colombia, Ecuador, Peru, and Bolivia. El Libertador (‘The Liberator’) as he would come to be known would die in 1830 aged only 47. His legacy, however, would continue to resonate through South American politics.