Sir Humphrey Gilbert (1539-1583) had a lot of hard bark on him. He was what is called in Britain a “West Countryman.” That is, he came from the jagged bit of southwestern England that juts out toward the Atlantic. It’s a poor country. The farmland isn’t very good, the sea is all around, and boys—noble or common–often went to sea. The better-off often went into politics as well. His half-brother was Sir Walter Raleigh and his cousin was Sir Richard Grenville. All three ended up dead as the result of “mishaps” at sea. (But not before they had done stuff to make their names ring out on street-corners.) He got the usual upper-class education, including—comically, given his behavior—a time studying law. Being “choleric” (i.e. he ran hot), he soon abandoned the law for war in France and Ireland.
While young, he got a taste for overseas empire-building at the expense of the locals. Essentially, his plan was to seize lands abroad; then to conquer, drive off, or kill the local inhabitants; and then to bring in English settlers. First he pursued his project in Ireland in the 1560s. The results were bloody in an extreme. His ruthless success in Ireland brought him a knighthood, election as a Member of Parliament, and a wide range of important contacts in science, trade, and government.
At the same time as he pursued empire in Ireland, dreams entered his head of even bigger projects in America. He had become one of the believers in the existence of a Northwest Passage across the top of America to China. He planned to capture the key point of entry into that passage for Britain. In practice, this meant establishing a colony on Newfoundland. The colony would command the entrance to Davis Strait between Greenland and the Canadian mainland, and to whatever lay beyond. No one really knew. Over-seas expeditions required ships, supplies, crews: in short a lot of money before they even left port. Queen Elizabeth I did not oppose such efforts, so long as somebody else paid for them. Gilbert invested much of his own wealth in the effort, then got some of his family-members to invest as well.
His first expedition sailed into the North Atlantic in November 1578. Storms kept it from reaching America. Years passed before Gilbert could raise the money for another expedition. Irish troubles continually demanded his attention. He proposed a plan to settle English Catholics in America so that they could practice their faith in freedom, but it failed to win approval.
His second expedition sailed in June 1583, although short of supplies, and reached Newfoundland in August. He took possession of the territory for England. Sailing down the coast, Gilbert’s usual bad luck at sea returned. His largest ship, with most of the supplies, went aground and sank. Gilbert headed the two surviving ships for home, hoping to return before the winter storms. In early September, they were caught in a huge, multi-day storm. Gilbert sat in a chair on the stern of his ship reading a book. When the other ship approached, Gilbert called out “we are as near to Heaven by sea as by land.” That night his ship sank with all hands.
Today Gilbert’s dream of an American colony to control the Northwest Passage seems ridiculous. It was a speculation founded on hope and ignorance. However, the dream of a Northwest Passage wasn’t any more ridiculous than the beliefs that inspired Columbus to sail west for China. Gilbert lacked Columbus’s skill as a sailor and his incredible good luck. Therefore, his dreams and projects ruined him.
Still, the application of “Irish” methods to America, British control of the seas to give it control of world trade, and colonies for religious dissidents all came to pass by-and-by.
 Family and friend investing may seem strange today, but it once was common. Families rose (or fell) together.