For Robert Dudley fate had found a kindred spirit, mentor, role model and life-long friend all in one.
In 1591, at the age of seventeen, Dudley married Margaret Cavendish, but she soon died without issue.
As he turned twenty, Dudley was eager to follow Elizabeth's `sea dogs' to the Pacific.
He was able to attract many famous officers, among them the navigator, Abraham Kendal, from whom Dudley said he learned enough for an Admiral; and as the captain of the Beare, his own cousin Thomas Jobson, who had served under Sir Francis Drake at San Domingo; and Captain Benjamin Wood, who had been to Virginia in 1584 and with Sir Walter Ralegh in the Azores in 1586.
Accepting the division of his force as an act of God, Dudley sent orders to captain Monck of the Beare's Whelpe to meet him in the Canary Islands or off the African mainland at Capo Blanco, a rendezvous his kinsman never kept.
Misfortune followed Dudley to the northern coast of Spain, where high seas in the Bay of Biscay swamped the Earwig, requiring him to take her crew aboard the Beare, then overcrowded with 140 souls.
Going on south to Guiana himself in the Beare, Dudley took along a Spanish-speaking Indian from Trinidad, who offered to guide the English adventurers up the Orinoco River, ostensibly to a gold mine.
With that setback, General Dudley quit Guiana, returning to Trinidad for refreshing before heading north on March 12th in the hopes of falling upon some storm-scattered stragglers from the annual Spanish gold convoy.
With provisions low, Dudley sailed for home, but ran into a Spanish man-o'-war of 600 tons.
The next year, Dudley took part in the `counter-Armada' under the earls of Essex and Nottingham, his uncle, which caught the Spanish fleet in harbour at Cadiz, destroyed it and sacked the port.
Shortly after Cadiz, Dudley married his second wife Alice Leigh (1579-1666), with whom he had five daughters.
In May 1603, a few weeks after the death of the old Queen, Dudley began legal proceedings to obliquely and quietly establish his legitimacy, but the case wound up in the Court of the Star Chamber.