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The old heroes, or anti-heroes, of the early Atlantic still have their place in history since they epitomise the activities of the many sailors and financiers from Italy and from Flanders, as well as from Spain and Portugal, who were pioneers in the colonial empires of the tropics. Columbus was a cloth merchant from Genoa who belonged to an integrated web of Italian traders from the western Mediterranean, many of whom had settled in the Atlantic ports of Lisbon and Seville. Henry was a royal prince of Portugal, a grandson of the great English warrior John of Gaunt, and as a very young soldier he took part in a famous raid across the ‘Pillars of Hercules’ into Africa. Both men were children of their time and both received a mixed reception at the hands of historians. The reputation of Columbus peaked in 1892, the quatercentenary of his ocean crossing, before the white peoples of the New World had grasped the scale of the devastation that he had brought in his wake. Henry’s reputation lasted half a century longer, and in 1960, five hundred years after he died, Portugal raised a monument to his memory while still clinging to an empire in Africa.