Unfortunately, game-playing and shell-inhaling did not leave the Tainos well prepared to defend themselves against the more aggressive Caribs (Indians from South America) nor the hot-on-their-heels Spanish settlers who arrived from Hispaniola with Juan Ponce de Leon in 1508. The settlers enslaved and evangelized the Tainos, exposing them to European diseases. The Tainos were soon extinct as a recognizable group; their myths, language and place names have lamentably faint resonance in Puerto Rican life today.

The Spanish settled at San Juan, which became one of the most strategic outposts in the New World. Over the next century it underwent massive fortification to protect it from British and Dutch maritime incursions. In response to a Spanish stranglehold on regional trade, Puerto Rico imported African slaves and dabbled with sugar, cotton and tobacco plantations in the 16th and 17th century, but there was more money to be made in black market trading with its neighbors.

Spain's inability to prevent smuggling undermined its moral authority on the island, and Puerto Rico began to develop its own distinct identity during the 18th century. This was enhanced by a growing number of immigrants and an emerging bourgoisie of coffee plantation owners. As revolution swept through the New World, Spain relaxed its totalitarian trade policies in a bid to keep Puerto Rico and Cuba in the colonial fold.

Spanish loyalists and Puerto Rican nationalists spent the second half of the 19th century arguing the pros and cons of self-rule with the colonial government. An unsuccessful revolt in the mountain town of Lares in 1868 focused everybody's mind on the seriousness of the problem at hand. A degree of autonomy was achieved in 1897, but this became obsolete almost immediately when US forces occupied Puerto Rico during the Spanish-American War.

The USA ruled Puerto Rico as a colonial protectorate for the next five decades, despite continued calls for autonomy. Puerto Ricans were granted US citizenship in 1917, just in time for them to be eligible for military service in WWI. Reform and investment improved the economy but the 1930s depression hit the island hard and the independence movement turned to violence. Puerto Rico won the right to elect its own governor in 1944 and "Operation Bootstrap", President Truman's New Deal for Puerto Rico, aimed to kickstart the island's economy, largely by giving tax breaks to resident US companies.

Puerto Ricans voted three to one in a 1951 referendum to become a commonwealth of the US rather than stay a colony. Nationalists seeking full independence took the fight to the US mainland where they attempted to assassinate President Truman and opened fire on US congressmen from the visitors' gallery in the House of Representatives. Political support for full independence waned and calls for US statehood increased. Although the Puerto Rican economy continued to improve, around two million Puerto Ricans took advantage of their US citizenship to seek work in New York City.

The island has a high standard of living compared to most other Caribbean islands, but it still languishes behind the poorest US states and continues to suffer high unemployment. Puerto Ricans voted in 1993 and 1998 for commonwealth status in preference to statehood, though the margins have not been decisive. The statehood debate continues, both on the island and in Washington, DC. Meanwhile, Puerto Ricans' ability to effect their own future is curtailed by an inability to vote in US national elections.

A massive restoration project was kick-started by 1993's 500th anniversary of Columbus' sighting of Puerto Rico. Many of San Juan's old buildings were lying derelict and in disrepair - preservation and reinvigoration has turned the quaint into the magnificent, and the walled city is now a major tourist destination in itself. Though nationalists have kept the independence debate on the national agenda, in reality San Juan remains a cultural beachhead for spreading US influence throughout the Caribbean.