The first settlement in Van Diemen's Land was founded in 1803, when a penal establishment, to which the more refractory of the prisoners in Sydney might be despatched, was founded on the banks of the River Derwent. Subsequently other penal stations were opened, and of these we shall hear later. The island continued to be the chief penal establishment of New South Wales until 1825, when it was erected into an independent colony. The first shipment of convicts, direct from England to Van Diemen's Land, took place in 1823, and from that date, until transportation to the island finally ceased, in 1853, 64,306 convicts were sent to that colony from the British Isles. The number sent previously from New South Wales was not large, nevertheless it included the majority of the most turbulent of the convicts and relieved the mother colony of their charge and control. The island was in fact "nothing but a jail on a large scale."[16] The early conditions in the colony appear to have been favourable to bushranging. In 1805 there was such a dearth of food stuffs, owing to the non-arrival of store ships from Sydney, that a famine appeared to be imminent and, to relieve the store, the Lieutenant Governor ordered the liberation of the convicts and sent them into the woods to catch kangaroo and other wild animals for food. When the stores arrived and food became plentiful, the attempts to recall the convicts were only partially successful. Many had learned how to subsist in the bush and disregarded the proclamations issued by the Lieutenant Governor ordering them to return to work. At first the bushrangers or bolters were similar to those of New South Wales and contented themselves with petty thefts. The first proclamation in which reference is made to "a gang of bushrangers" was published in the Hobart Town Gazette by Lieutenant Governor Davey and dated September 10th, 1810. It offered rewards and indulgences to convicts for the capture of any members of a gang which, under the leadership of a convict named Whitehead, had been committing depredations on the property of settlers and farmers in the vicinity of Hobart Town.

Whitehead, therefore, was the first to organise a gang which combined highway robbery with burglary and petty larceny. Bushrangers were not at that time specialists. From time to time other proclamations were issued in which this gang was mentioned, but it was not until May 14th, 1813, that a special proclamation was published, calling upon the "bolters" to surrender. Those who neglected to obey this order were to be proclaimed "outlaws" on December 1st.

Very few particulars are published about this gang in the newspapers, and the proclamations rarely specify the facts in connection with the robberies committed. The newspapers of the time seldom mention the names of the bushrangers, and appear to have been quite as averse to mentioning the Christian names as the modern English papers are those of professional cricketers. Thus Whitehead is referred to as "the convict Whitehead," or the "notorious bushranger Whitehead," and so on. He is debited, however, with one horrible crime. The gang captured a half-crazy fellow named John Hopkins, and accused him of trying to betray them. As a punishment for this offence a pair of moccassins, roughly made of bullock hide, was fitted on to his feet, and in these were placed a number of the great red ants, commonly known in Australia as "bull-dog" or "soldier" ants (myrmecia gulosa). These ants are an inch and a quarter long, and of most ferocious appearance. They are the dread of the colonists. They sting quite as severely as a bee or a hornet. But a bee stings only once, while a soldier ant will continue to sting until removed. It is always ready to fight, and never lets go when it has taken hold; hence its popular names. The horrible barbarity of such a punishment can be best appreciated, perhaps, by those who have inadvertently stood on a "soldier's" bed or nest. The victim is said to have died in agony.

Whitehead was shot by a party of soldiers in October, 1814, and Michael Howe, commonly called the "First of the Australian Bushrangers," was elected captain of the gang in his stead. Mike Howe, as he was usually called, was transported from England for highway robbery, and soon after his arrival at Sydney "got into trouble," and was again transported to Van Diemen's Land, where his violence caused him to be repeatedly flogged and otherwise punished. He made his escape and joined Whitehead's gang, and soon, by his superior education, gained an ascendency over his comrades. His previous experiences as a footpad in England no doubt tended to fit him for the leadership of the gang, and he is still regarded as one of the most notable of the revolters against law and order in the colonies. One of his earlier achievements was to organise a raid on a tribe of blacks for the purpose of providing himself and his comrades with wives. This is said to have been the first act in the tragedy which closed with the complete annihilation of the blacks of the island. The savages, of course, resisted, and many of them were shot, and the women were forced away to the bushrangers' camp. In revenge, the blacks attacked, not the bushrangers' camp, but the houses of settlers who had no connection with the bushrangers, and fights between the settlers and the blacks became frequent. Some of the black women seem to have become reconciled to the change, and Howe's "wife," Black Mary, is associated with him in most of the stories told of him. It is said that it was her knowledge of the bush which enabled him to escape so frequently from the military bands sent out to capture him.

Howe addressed a letter "From the Bushrangers to the Hon. T. Davey, Lieutenant Governor of Van Diemen's Land," in which he protested against the charge, made against himself and his mates in the proclamations, of having been guilty of "horrid and detestable crimes." He asserted that he had never committed murder and had only used violence when it was necessary to avoid capture. The letter was conveyed to Hobart Town by an American whaler named Richard Westlick, who had an interview with his Excellency, and was sent back with a verbal message that the Governor "did not wish to take the life of any man," but merely to preserve order. If, therefore, Howe, or any of his comrades, would surrender no charges should be made against them for their acts while "in the bush." No notice was taken of this generous offer, and the depredations continued. Later on Mike Howe addressed a letter "From the Governor of the Ranges to the Governor of the Town," and sent it to Lieutenant Governor Sorell, who had succeeded Colonel Davey. In this the bushranger offered to give himself up on condition that he received a free pardon. He demanded that some recognised official should be sent to meet him at an appointed spot, so that they might "confer as gentleman to gentleman." The fact that this insolent offer was accepted affords incontrovertible evidence of the power of the bushrangers, and shows the anxiety of the Governor to put a stop to the robberies which harassed the industrious settlers and made the roads of the colony unsafe. Captain Nairne, of the 46th Regiment, was sent out to meet the bushranger, and the result of their conference "as gentlemen" was that Howe accompanied the Captain back to Hobart Town. On his arrival there he was informed that the Lieutenant Governor had no power to grant pardons, but that he would write to Governor Macquarie in Sydney and urge him to grant a pardon without delay. Howe agreed to wait in Hobart Town. He was liberated on parole, and soon became very popular in the city. Then a rumour began to spread to the effect that Howe had committed no less than four murders, not reckoning the blacks he had killed, and that, therefore, the Governor declined to grant him a pardon. As soon as Howe heard this rumour he, without waiting for its confirmation, broke his parole and returned to the bush. A proclamation was immediately issued declaring him an outlaw, and offering one hundred pounds reward for his capture, dead or alive. Smaller rewards were offered for other members of his gang, whose names were known.

The estimates of the strength of his gang vary extremely from time to time. Sometimes he is said to have a hundred or more followers, while frequently he is represented as acting alone or in company with only one or two others. The facts appear to be that many men, who merely "bolted" into the bush as a relief to the monotony of their lives, became bushrangers; and, when hard pressed, or when they tired of that pursuit, returned to the town, gave themselves up, and were punished as ordinary bolters. One day, not very long after his escape from Hobart Town, Howe was surprised while asleep by two ticket-of-leave men named Watts and Drew. They captured and tied him. Howe fought like a lion and contrived to break the rope with which he was tied. He snatched a knife and stabbed Watts. He then seized Watts' gun and shot Drew dead. Watts ran away, while Howe was employed in re-loading the gun, and managed to secrete himself in the scrub for a time. When the way was clear he crawled to a farm and gave information. He was cared for as well as circumstances permitted, but he died from loss of blood before a doctor could be brought to him. Howe was followed by the military, but escaped.

Several skirmishes took place between Howe and his gang and the soldiers, and more than one of his accomplices were shot, but the chief always contrived to get away. At length a kangaroo hunter named Warburton led William Pugh, a soldier commonly known as "Big Bill," and a seaman named John Worrall, to where Howe was camped under a gum tree. A terrific fight took place, Howe's brains being beaten out before it was over.

In his review of this period, Mr. J.T. Bigge said: "The excesses of the bushrangers in the neighbourhood of Port Dalrymple, and likewise near Hobart Town, had attained their utmost height and most sanguinary character at the latter end of the year 1813. They had been joined by two persons who had held subordinate stations in the commisariat department, named Peter Mills and George Williams, and continued a system of violent depredations upon the homes and property of individuals of every description. So great was the intimidation produced by their combined efforts, that the inhabitants of several districts abandoned their dwellings and removed for safety to the towns.... Colonel Davey issued a proclamation offering rewards for the apprehension of a party of nine, and with the advice of Mr. Ellis Bent another proclamation calling upon them to surrender before December 1st.... The effect of this was the reverse of what was intended. It increased the crimes and audacity of the bushrangers during the six months that it allowed for their return; they profited by the pardon by making a temporary surrender, and then resumed their habits of plunder.... Hector McDonald, the leader, was shot by two convicts sent in pursuit of a gang of four. Another was shot by a soldier of the 48th regiment, and the other three were captured and on conviction flogged and transported."[17]

For the time, bushranging in Van Diemen's Land was said to have been put down, but "the Guerilla War" between the whites and the blacks, inaugurated by the bushrangers, continued. Mr. Gilbert Robertson was appointed conciliator, with a view to arranging terms of peace, but he was not very successful. Several proclamations were issued assuring the blacks that if they would come in and make peace the Government would endeavour to protect them against their enemies the bushrangers; but, as was pointed out at the time, issuing proclamations to savages who could not read was absurd. Then a pictorial proclamation was issued. In one portion the governor was shown shaking hands with a blackfellow; in others blacks and whites were exhibited mingling together in friendship. In the two bottom compartments a white man was shown being hung for having shot a black, while a blackfellow was being hung for having speared a white man. Copies of this pictorial proclamation were posted on trees and other places where the blacks might see it. Lieutenant Governor Arthur in fact, on his arrival in the colony, tried by every means in his power to appeal to the blacks and whites alike. He endeavoured to restrain the settlers from attacking and driving the blacks away from their farms whenever they appeared, as had become the custom, but some new outrage by the bushrangers gave a new impulse to the feud, and the settlers were compelled to fight in self-defence. In one of his despatches to the Colonial Secretary Governor Arthur said: "It is not a matter of surprise that the injuries real or supposed, inflicted on the blacks, have been avenged upon the whites whenever an occasion presents itself; and I regret to say that the natives led on by a Sydney black, and by two aborigines of this island, men partially civilised (a circumstance which augurs ill for any endeavour to instruct these abject beings), have committed many murders upon the shepherds and herdsmen in remote settlements.... I have long indulged the expectation that kindness and forbearance would have brought about something like a reconciliation, but the repeated murders which have been committed have so greatly inflamed the passions of the settlers, that petitions and complaints have been presented from every part of the colony, and the feeling of resentment now runs so high that further forbearance would be totally indefensible."[18]

The Sydney black here mentioned was known as Musquito. He was transported to Van Diemen's Land for the murder of a black gin (presumably his wife, which is no crime according to native law) in 1823, and having been employed on a cattle station in New South Wales, was appointed stock-keeper. Later, he was employed as a tracker, and aided the soldiers in capturing some of the bushrangers. For this he was so persecuted by his fellow convicts that life became a burden to him. He appealed to the authorities for protection; but, as this was not accorded to him, he became a bushranger himself. "Perhaps taken collectively the sable natives of this colony are the most peaceable creatures in the universe. Certainly so taken they have never committed any acts of cruelty, or even resisted the whites, unless when insufferably goaded by provocation. The only tribe who have done any mischief were corrupted by Musquito, a Sydney black, who, with much perverted cunning, taught them a portion of his own villainy, and incited them after a time to join in his delinquencies."[19]