The court of Queen Elizabeth I was a dour place, filled with sycophants decked out in the drab black cloaks fashionable at the time. But then Walter Raleigh showed up, dressed like a peacock in garish colors in a dizzying array of expensive fabrics like silks and damasks. Raleigh certainly dressed to impress – in 1584, he reported the theft of three clothing items worth almost £115 – which was more than enough money to run an entire household (including servants) for an entire year!
But Raleigh came to court with more than just nice clothes. He was intelligent, witty, and just plain charming. It was Walter Raleigh, for example, who allegedly laid one of his expensive cloaks over a mud puddle so that Elizabeth wouldn’t dirty her royal feet. He could play music, write poetry, flirt and talk about almost any issue in his West Country accent, which Elizabeth found perfectly adorable.
She quickly began lavishing gifts on Raleigh, from titles and royal appointments to estates and monopolies. It was the monopolies on wine licenses (granted by Elizabeth in 1583) and the export of wool (1585) that gave Raleigh immense wealth that he used to buy more of his beloved expensive clothes, to spare no expense in redecorating and refurbishing the estates that Elizabeth had given him, and to fund an entourage of 30 servants (each of whom needed their own set of fancy clothes, too!). Raleigh quickly rose from a virtual nobody to become one of the richest men in England, and he used his wealth in ways and quantities that shocked and staggered his contemporaries. Raleigh, indeed, threw money around in ways that would make even the gaudiest hip-hop mogul of today hang his head in disgust.
But Raleigh was more than just flash. He had a dream… a dream of an English colony in the wilderness of America. In 1584, Raleigh sent his first colony to Virginia (which then comprised a section of what would later become North Carolina). The colonists landed at Roanoke Island in present-day Dare County, North Carolina. The colonists would suffer greatly due to lack of food (mainly caused by poor selection of colonists) and troubled relations with local Indian tribes. The expedition ended in failure in 1586.
Raleigh found himself unable to fund a second trip on his own, so a joint-stock company was created. When enough investors had been lined up, Raleigh launched a second expedition in 1587. This group of colonists were supposed to stop by Roanoke Island and pick up a few soldiers left to guard the settlement after the first expedition left. They were then to settle somewhere north on Chesapeake Bay. However, Simon Fernandez, the captain of the colony’s main ship, the Susan Constant, unceremoniously dumped the colonists on Roanoke Island on July 22, 1587, as he wanted to get to the Caribbean as quickly as possible to loot Spanish treasure ships.
Although Raleigh and company promised the colonists a steady stream of supply ships, it wasn’t to be. By the time John White (a friend of Raleigh’s and overall commander of the expedition) arrived back in England from Roanoke, it was too late in the year to return to Virginia. Then the Spanish Armada sailed towards England, and every ocean-worthy ship was commandeered for the defense of the realm. White managed to get a special dispensation from the Queen to allow two small ships to sail to Roanoke in 1588, but the captains of these ships were greedy and tried to capture Spanish ships while in transit; instead, they were captured and the venture was a total loss.