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| - De With was born on a farmstead in the hamlet of Hoogendijk near Brielle or Brill, the very town in which Maarten Tromp had been born a year earlier. According to legend they were friends or even already rivals in their youth, but there is no proof for this. His father died in 1602, leaving behind three sons, besides Witte also Abraham and Andries, and a daughter Catharina. The De With family were Mennonites and strict pacifists; in 1610 Witte, as an anabaptist not yet baptised, obtained a baptism by a Calvinist preacher so that he would no longer feel constrained in using violence as he was by nature not a peace-seeking boy. After some failed minor jobs he went on his first sea voyage to the Dutch East Indies on 21 January 1616 when he was sixteen, as a cabin boy on Captain Geen Huygen Sc
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| - De With was born on a farmstead in the hamlet of Hoogendijk near Brielle or Brill, the very town in which Maarten Tromp had been born a year earlier. According to legend they were friends or even already rivals in their youth, but there is no proof for this. His father died in 1602, leaving behind three sons, besides Witte also Abraham and Andries, and a daughter Catharina. The De With family were Mennonites and strict pacifists; in 1610 Witte, as an anabaptist not yet baptised, obtained a baptism by a Calvinist preacher so that he would no longer feel constrained in using violence as he was by nature not a peace-seeking boy. After some failed minor jobs he went on his first sea voyage to the Dutch East Indies on 21 January 1616 when he was sixteen, as a cabin boy on Captain Geen Huygen Schapenham's ship the Gouden Leeuw, part of a Dutch East India Company (VOC) fleet of five vessels. He arrived at Bantam on 13 November 1616. Until October 1617 he participated in two trade voyages to Coromandel in India. Afterwards he became manservant of governor Jan Pieterszoon Coen. He served as a corporal during the siege of Jakarta in 1618. On 8 October 1618 he sailed home on the Gouden Leeuw, returning to Brill on 23 May 1619. On 20 August 1620 he took service with the Admiralty of the Maze as a schipper (then the highest NCO rank), still under Schapenham on the Gelderland. From December 1620 the Gelderland participated in an expedition by Admiral Willem de Zoete against the Barbary Corsairs, returning in August 1621. In the Spring of 1622 De With was appointed lieutenant on Schapenham's vessel. When the latter became ill, De With functioned as commandeur, acting captain, of the Gelderland during convoy duty in the Baltic. When Schapenham recovered, De With served for a short period on the Maurits to protect the herring fleet. In July 1622 De With became flag captain of Delft of now Vice-Admiral Schapenham, who from 29 April 1623 carried out the spectacular raid organised by the Admiralty of Amsterdam, sending the so-called "Nassau fleet" against the Spanish possessions on the west coast of America; this fleet rounded Cape Horn in March 1624. On his first voyage as a captain, De With already showed he was the strict disciplinarian of later legend: on 13 April six of his men deserted his ship, and the constant beatings and floggings, to flee to the uninhabited island of Juan Fernández. Until October the fleet attacked Spanish shipping and settlements; during one of the actions De With was wounded by a musket bullet. Then it crossed the Pacific, sailing via the Mariana Islands to the Indies. Reaching Ternate in the Spice Islands on 5 March 1625, De With himself on request of the governor of Ambon in a punitive action laid waste to island, destroying by his own count 90,000 clove trees of the inhabitants, to increase the price of this commodity. He departed for the Republic on 6 February 1626, after the death of Schapenham, as Vice-Admiral (in service of the Verenigde Oostindische Compagnie) of a Spice Fleet of four ships, then worth five million guilders. He returned on 22 September 1626, thus having circumnavigated the globe, a feat in which he took much personal pride. On his return he learned that his mother and sister had died; he remained on shore for one and a half years.
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