Sources of Pride and Strength
The circumstances and conditions that have a determining influence upon a man's life and character often antedate, by many years, his own conscious existence….
When he first becomes conscious of himself and his environment, he is already caught
in a web of external relations, conditions and circumstances from which he seldom
—George Kennan, Autobiography
For a time early in the nineteenth century the Harriman family seemed destined to an inglorious end in a watery grave. Three of William Harriman's sons met with death at sea in very different ways. The eldest, William, died in a naval clash between English and French ships. Alphonso drowned in the waters off the Battery after the family moved to New York, and Edward simply vanished. His father had made him master of cargo on one of the vessels he fitted out for the West Indies, but the ship never reached port and was never heard from again. Three other sons had died in childhood, leaving only one to carry on the family name. Orlando did not need his mother's fervent pleas to spurn adventure at sea in favor of joining his father in business. Upon that frail reed rose the Harriman dynasty. 1
From the first it was shrouded in mystery. No one knows what induced William to leave his comfortable life as a stationer in London. He was said to be in sympathy with the colonial cause, yet he did not sail for America until April 1795, long after the issues of war and peace had been decided. He was not a poor man; some of his neighbors in New Haven, where he first resided, liked to refer to him as “the rich Englishman.” Nor was it a move to be lightly considered. William brought with him the baggage of a full life: a wife, six children, and his wife's sister, Rosamond Holmes. Whatever pushed or pulled him across the sea had to be of more than ordinary force.
Once settled in New Haven, William tried his luck at the West Indies trade until the treacherous currents of commerce swallowed most of the money he had brought from England. After a few years he took his family to New York City, where he gradually shifted from shipping to a general commission business. There William prospered in a modest way, and young Orlando did well