In November 1789 a substitute for Arabanoo was sought resulting in the capture of Bennelong and Colebee at Manly Cove. Phillip had sent a party to the Cove in an attempt to deal with what the British regarded as the most influential group – the Gamaragal. Instead they captured a Wangal (Bennelong) and a Cadigal (Colebee). Their presence among the Gamaragal may have been the result of normal relations between the groups or as a result of impacts of ‘smallpox’ on both the Wangal and Cadigal and the dislocation of survivors from these groups.
The task of carrying out the abduction on 25 November 1789 fell to Lieutenant William Bradley who remarked that the ‘crying & screaming of the women and children together with the situation of the two miserable wretches in our possession was really a most distressing scene; they were much terrified’. Bradley added that ‘it was by far the most unpleasant service I was ever ordered to Execute’. Tench, who was not present, remarked at the ease of which the two men were captured.
Following capture and return to the settlement they were identified by name by Nanbarry and Boorong. Imprisoned – both refused to communicate and attempted escape at the first opportunity – Colebee escaped seventeen days later but Bennelong remained in captivity. With the more senior Colebee gone Bennelong began to converse with his captors. Bennelong was interviewed throughout his captivity and provided names for the people inhabiting the Port Jackson region as well as language, family connections and some cultural information.
That Bennelong remained in captivity may have been not so much a matter of choice on Bennelong’s part but a requirement to learn something of the habits, customs and strength of the newcomers. Some of the information provided by Bennelong during this first phase of contact was confusing. He regarded the Gamaragal as enemies and sought assistance to exterminate them but then quickly changed his mind. Later events would suggest that his relationship with the Gamaragal may have been one of dependence following the break-down of the traditional Eora social structure and that he continued to maintain close contact with them. Alternatively Bennelong may have been attempting to encourage direct and open conflict with the Gamaragal in order to bring matters to a head. With Colebee at large the arrangement of such encounter was feasible. Time spent in the settlement however, may have tempered such a stratagem.
Bennelong communicated with a number of officers within the settlement. Time spent with Lieutenant William Dawes helped the language spoken by the Eora to survive to this day. Although Bennelong was not the primary informant he did provide information regarding places and people, as well as grammar, to Dawes.
The officer with whom Bennelong developed the closest relationship was Governor Phillip. What developed was a respectful relationship between men of seniority within their own communities. Phillip, being the older man, was however the senior of the two. Bennelong recognised this by an exchange of names and reference to Phillip as “father”. This may have been an attempt to open a new phase of dealing with the invaders – negotiation. Whether this was self-serving on Bennelong’s part or a plan that would preserve the livelihood of the survivors of the epidemic is unclear. Bennelong certainly benefited in the short-term and would later use this period of captivity to further his position within the surviving Eora communities.
Bennelong’s apparent compliance and willingness to absorb both the language and customs of his captors seemed to indicate that a reliable interlocutor between the two societies had been found.
In March 1790 the loss of the Sirius on Norfolk Island placed the Colony at Port Jackson in peril with a reduced capacity to obtain supplies and to communicate with the world beyond Port Jackson. The settlement was placed on reduced rations with no clear end to the situation in sight. The vulnerability of the settlement was concealed from Bennelong by providing him with as much food as could be gathered.
In May 1790 Bennelong escaped from captivity and generally avoided any contact with Europeans in the period immediately thereafter. He had been detained for almost six months and during that period gained knowledge of his captors’ language, customs and strength.
Phillip reflected on Bennelong’s escape in a letter to Sir Joseph Banks in which he stated that ‘our native has left us, & that at a time when he appeared to be happy & contented … I think that Mans leaving us proves that nothing will make these people amends for the loss of their liberty’.
Bennelong’s next encounter with his former hosts took place on 7 September 1790. A small party under Captain Nepean with Nanbarry as interpreter landed at Manly Cove with the intention of exploring the land northward to Broken Bay. At Manly Cove the party came upon up to 200 people feasting on the carcass of a beached whale.
When informed that the Governor was not far-off an invitation was extended to Phillip to attend. Phillip arrived shortly after and resumed what appeared to be a friendly dialogue with Bennelong.
A spear described by Phillip as “being longer than common, and appeared to be a very curious one, being barbed and pointed with hard wood” was placed on the ground by Bennelong. On being introduced to Willemering, a stranger in their midst, Phillip approached him at which point Willemering picked up the spear and hurled it into Phillip’s shoulder. The inactivity of both Bennelong and Colebee may indicate that the spearing had been orchestrated by them as ritual payback for their time in custody, and in order to restore any influence lost by Bennelong’s detention. The British saw this action as a misinterpretation of Phillip’s advances to someone unfamiliar with Europeans. If the spearing was payback then the action was organised at very short notice.  Whether deliberate or accidental the spearing had a significant effect on relations between the two communities. There was no retribution and perhaps for Eora – and Bennelong in particular – there had been redress for his imprisonment.
 crying & screaming of the women and children together with the situation of the two miserable wretches in our possession was really a most distressing scene; they were much terrified. (Bradley 1969: 181–183)
 Nanbaree and Abaroo welcomed them on shore; calling them immediately by their names, Ban-ee-lon, and Col-bee. But they seemed little disposed to receive the congratulations, or repose confidence in the assurances of their friends. The same scenes of awkward wonder and impatient constraint, which had attended the introduction of Arabanoo, succeeded. (Tench 1793 : 159)
 But Baneelon, though haughty, knew how to temporize. He quickly threw off all reserve; and pretended, nay, at particular moments, perhaps felt satisfaction in his new state. Unlike poor Arabanoo, he became at once fond of our viands, and would drink the strongest liquors, not simply without reluctance, but with eager marks of delight and enjoyment.
He was the only native we ever knew who immediately shewed a fondness for spirits: Colbee would not at first touch them. Nor was the effect of wine or brandy upon him more perceptible than an equal quantity would have produced upon one of us, although fermented liquor was new to him.
In his eating, he was alike compliant. When a turtle was shown to Arabanoo, he would not allow it to be a fish, and could not be induced to eat of it.
Baneelon also denied it to be a fish; but no common councilman in Europe could do more justice than he did to a very fine one, that the 'Supply' had brought from Lord Howe Island, and which was served up at the governor's table on Christmas Day. (Tench 1793 : 159-160)
 Whenever he recounted his battles, "poised his lance, and showed how fields were won", the most violent exclamations of rage and vengeance against his competitors in arms, those of the tribe called Cameeragal in particular, would burst from him. And he never failed at such times to solicit the governor to accompany him, with a body of soldiers, in order that he might exterminate this hated name. (Tench: 160)
 Again, as a mark of affection and respect to the governor, he conferred on him the name of Wolarawaree, and sometimes called him 'Beenena' (father),adopting to himself the name of governor. This interchange we found is a constant symbol of friendship among them.(Tench 1793 : 160-161)
 In a word, his temper seemed pliant, and his relish of our society so great, that hardly any one judged he would attempt to quit us, were the means of escape put within his reach. Nevertheless it was thought proper to continue a watch over him. (Tench 1793 : 161)
 Our friend Baneelon, during this season of scarcity, was as well taken care of as our desperate circumstances would allow. We knew not how to keep him, and yet were unwilling to part with him. Had he penetrated our state, perhaps he might have given his countrymen such a description of our diminished numbers, and diminished strength, as would have emboldened them to become more troublesome. Every expedient was used to keep him in ignorance.
His allowance was regularly received by the governor's servant, like that of any other person, but the ration of a week was insufficient to have kept him for a day. The deficiency was supplied by fish whenever it could be procured, and a little Indian corn, which had been reserved was ground and appropriated to his use. In spite of all these aids, want of food has been known to make him furious and often melancholy. (Tench 1793 : 167)
 There is reason to believe that he had long meditated his escape, which he effected in the night of the 3rd instant. About two o'clock in the morning, he pretended illness, and awaking the servant who lay in the room with him, begged to go down stairs. The other attended him without suspicion of his design; and Baneelon no sooner found himself in a backyard, than he nimbly leaped over a slight paling, and bade us adieu. (Tench 1793 : 167)
 (Phillip to Banks, 26 July 1790, Banks Papers, Mitchell Library, Series 37.12–20.cited in Fullagar (2009): 34)
 On the 7th instant, captain Nepean, of the New South Wales corps, and Mr. White, accompanied by little Nanbaree, and a party of men, went in a boat to Manly Cove, intending to land there, and walk on to Broken Bay. On drawing near the shore, a dead whale, in the most disgusting state of putrefaction, was seen lying on the beach, and at least two hundred Indians surrounding it, broiling the flesh on different fires, and feasting on it with the most extravagant marks of greediness and rapture. As the boat continued to approach, they were observed to fall into confusion and to pick up their spears, on which our people lay upon their oars and Nanbaree stepping forward, harangued them for some time, assuring them that we were friends. Mr. White now called for Baneelon who, on hearing his name, came forth, and entered into conversation. He was greatly emaciated, and so far disfigured by a long beard, that our people not without difficulty recognized their old acquaintance. His answering in broken English, and inquiring for the governor, however, soon corrected their doubts.He seemed quite friendly. And soon after Colbee came up, pointing to his leg, to show that he had freed himself from the fetter which was upon him, when he had escaped from us.When Baneelon was told that the governor was not far off, he expressed great joy, and declared that he would immediately go in search of him, and if he found him not, would follow him to Sydney. "Have you brought any hatchets with you?" cried he. Unluckily they had not any which they chose to spare; but two or three shirts, some handkerchiefs, knives, and other trifles, were given to them, and seemed to satisfy. Baneelon, willing to instruct his countrymen, tried to put on a shirt, but managed it so awkwardly, that a man of the name of M'Entire, the governor's gamekeeper, was directed by Mr. White to assist him. This man, who was well known to him, he positively forbade to approach, eyeing him ferociously, and with every mark of horror and resentment. He was in consequence left to himself, and the conversation proceeded as before. The length of his beard seemed to annoy him much, and he expressed eager wishes to be shaved, asking repeatedly for a razor. A pair of scissors was given to him, and he shewed he had not forgotten how to use such an instrument, for he forthwith began to clip his hair with it. (Tench 1793 : 183-184)
 Phillip in Hunter 1793:462
 When the boat reached Manly Cove, the natives were found still busily employed around the whale. As they expressed not any consternation on seeing us row to the beach, governor Phillip stepped out unarmed, and attended by one seaman only, and called for Baneelon, who appeared, but, notwithstanding his former eagerness, would not suffer the other to approach him for several minutes.
Gradually, however, he warmed into friendship and frankness, and presently after Colbee came up. They discoursed for some time, Baneelon expressing pleasure to see his old acquaintance, and inquiring by name for every person whom he could recollect at Sydney; and among others for a French cook, one of the governor's servants, whom he had constantly made the butt of his ridicule, by mimicking his voice, gait, and other peculiarities, all of which he again went through with his wonted exactness and drollery.
He asked also particularly for a lady from whom he had once ventured to snatch a kiss; and on being told that she was well, by way of proving that the token was fresh in his remembrance, he kissed Lieutenant Waterhouse, and laughed aloud. On his wounds being noticed, he coldly said, that he had received them at Botany Bay, but went no farther into their history.
Hatchets still continued to be called for with redoubled eagerness, which rather surprised us, as formerly they had always been accepted with indifference. But Baneelon had probably demonstrated to them their superiority over those of their own manufacturing. To appease their importunity, the governor gave them a knife, some bread, pork, and other articles, and promised that in two days he would return hither, and bring with him hatchets to be distributed among them, which appeared to diffuse general satisfaction.
Baneelon's love of wine has been mentioned; and the governor, to try whether it still subsisted, uncorked a bottle, and poured out a glass of it, which the other drank off with his former marks of relish and good humour, giving for a toast, as he had been taught, "The King."
Our party now advanced from the beach but, perceiving many of the Indians filing off to the right and left, so as in some measure to surround them, they retreated gently to their old situation, which produced neither alarm or offence. The others by degrees also resumed their former position. A very fine barbed spear of uncommon size being seen by the governor, he asked for it. But Baneelon, instead of complying with the request, took it away, and laid it at some distance, and brought back a throwing-stick, which he presented to his excellency.
Matters had proceeded in this friendly train for more than half an hour, when a native, with a spear in his hand, came forward, and stopped at the distance of between twenty and thirty yards from the place where the governor, Mr. Collins, Lieutenant Waterhouse, and a seaman stood.
His excellency held out his hand, and called to him, advancing towards him at the same time, Mr. Collins following close behind. He appeared to be a man of middle age, short of stature, sturdy, and well set, seemingly a stranger, and but little acquainted with Baneelon and Colbee. The nearer the governor approached, the greater became the terror and agitation of the Indian. To remove his fear, governor Phillip threw down a dirk, which he wore at his side. The other, alarmed at the rattle of the dirk, and probably misconstruing the action, instantly fixed his lance in his throwing-stick.
To retreat, his excellency now thought would be more dangerous than to advance. He therefore cried out to the man, Weeeree, Weeree, (bad; you are doing wrong) displaying at the same time, every token of amity and confidence.
The words had, however, hardly gone forth, when the Indian, stepping back with one foot, aimed his lance with such force and dexterity, that striking
the governor's right shoulder, just above the collar-bone, the point glancing downward, came out at his back, having made a wound of many inches long. The man was observed to keep his eye steadily fixed on the lance until it struck its object, when he directly dashed into the woods and was seen no more.
Instant confusion on both sides took place. Baneelon and Colbee disappeared and several spears were thrown from different quarters, though without effect.Our party retreated as fast as they could, calling to those who were left in the boat, to hasten up with firearms. A situation more distressing than that of the governor, during the time that this lasted, cannot readily be conceived: the pole of the spear, not less than ten feet in length, sticking out before him, and impeding his flight, the butt frequently striking the ground, and lacerating the wound. In vain did Mr. Waterhouse try to break it; and the barb, which appeared on the other side, forbade extraction, until that could be performed. At length it was broken, and his excellency reached the boat, by which time the seamen with the muskets had got up, and were endeavouring to fire them, but one only would go off, and there is no room to believe that it was attended with any execution. Tench 1793 :178-180)