On Tuesday, May 18th, 1841, a gentleman, mounted on a spirited horse, pulled up at the tollbar on the Parramatta Road, Sydney, and asked the toll-keeper if he could oblige him with a pipe of tobacco. The toll-keeper gave him a piece, and the gentleman dismounted and filled his pipe. As he stood at the door of the toll-house he remarked a firelock hanging over the mantelpiece, and asked what it was for. "For bushrangers," replied the toll man. "But there are none now. I've never seen it taken down since I've been here." "Did you ever hear of Jackey Jackey?" enquired the gentleman. "Oh, yes," replied the toll man, "but he's a long way away. He never comes to Sydney. If he did he'd soon be caught." "Not at all," replied the gentleman laughing. "They don't know how to catch him, nor to keep him when they do catch him. I'm Jackey Jackey." He raised the lappels of his coat as he spoke and showed a brace of pistols stuck in his belt on each side. The tollman looked very much alarmed, but the bushranger said to him, "Don't be frightened, I am not going to hurt you. I've been in Sydney for three days and I'm going back to Manaro." He informed the tollman that he had taken a horse in Sydney, but that he was too old and stiff, so he had taken the liberty of exchanging him for the one he had with him at Grose's Farm. "Ain't you afraid of being took?" asked the tollman. Jackey laughed. "I'd like to see who'll stop me while I've these little bull-dogs about me," he said, tapping his pistols. He stood chatting while he smoked regardless of the fact that Grose's Farm, now the grounds of the Sydney University, was within a stone's-throw of the tollbar. He offered the tollman some money and asked him to go to the public-house for some rum. The tollman replied, "I can't leave the bar." "All right," returned Jackey, "then I'll get it myself." He went away to Toogood's Inn and returned in a few minutes with half-a-pint of rum. He gave some to the toll-keeper and took a stiff glass himself. Then he shook hands with the tollman, mounted his horse, and rode on towards Parramatta.

On the 8th of July a great commotion was caused in George Street, Sydney, by a soldier arresting a well-dressed man and asserting that he recognised him as Jackey Jackey. A large number of people assembled and there were plenty of them quite ready to assist in the capture of the noted bushranger. On the prisoner being taken to the police court proof was soon forthcoming to show that he was a free man. He was discharged and the soldier was censured for being too officious. Since the visit of the bushranger in May had become known a constant look-out had been kept in case he should repeat his visit.

Jackey Jackey did not long maintain his freedom, however. He one day went into Gray's Black Horse Inn on the Berrima road, called for some refreshments, went into a sitting room, and threw himself on the sofa. He was served by Miss Gray, and while he was drinking she pounced on him and screamed. Her father and mother came to her assistance, but Jackey Jackey fought with so much determination that he would no doubt have got away. A carpenter named Waters was working near, however, and hearing the noise he rushed in and struck Jackey Jackey on the head with his shingling hammer. Knocked senseless, the noted bushranger was easily secured. It will be remembered that Gray's Black Horse Inn was about three miles from Mulligan's farm, and was the place where Lynch had bought the rum to treat Mr. and Mrs. Mulligan just before he murdered them. The capture of Jackey Jackey was effected for the purpose of securing the reward of offered for him dead or alive. He was tried for the robbery of the Boro store, and was sentenced to penal servitude for life. He was first confined in Darlinghurst Gaol, Sydney, but being detected in an attempt to escape, he was transferred to Cockatoo Island at the mouth of the Parramatta River. While here he organised a band of twenty-five prisoners, and made a desperate attempt to escape. The gang overcame and tied a warder, and then jumped into the harbour with the intention of swimming to Balmain. The water police, however, were apprised of the mutiny and captured the whole gang. It has been asserted that no prisoner has escaped from Cockatoo Island. The distance from the island to the shore is not very great, certainly less than half-a-mile to the nearest point, but all who have tried to swim it have either been retaken by the police or eaten by sharks.

The gang was tried for this attempt at escape and were sentenced to be sent to Port Arthur, Van Diemen's Land. Being such a desperate lot of scoundrels they were chained down in the hold of the brig, in which they were forwarded, for safety; but, in spite of this precaution, they contrived to get loose and were only prevented from capturing the brig by the hatches being put on and battened down. They reached Port Arthur in an almost suffocated condition, and were nearly starved, as they had had no food for several days; the captain of the brig not daring to remove the hatches, either to let in air, or to pass food to the prisoners.

Jackey Jackey succeeded in escaping from Port Arthur and immediately resumed his bushranging career. He was captured, however, after a very short run and was sent to Glenorchy Probation Station for milder treatment. Probably this attempt at reformation came too late, but however this may have been, it had little beneficial effect. Jackey Jackey made his escape and again began bushranging. He was captured in a house in Hobart Town and was sentenced to death. The sentence, however, was commuted to penal servitude for life and he was sent to Norfolk Island, where we shall hear of him again later on.

In the meantime, Jackey Jackey's old mate, Paddy Curran, continued to rob as before. He went to Major Lockyer's station and entered the men's hut while they were having their Christmas dinner, in 1840. He had a pair of handcuffs hanging at his belt, and was therefore thought to be a constable out on the spree. He helped himself freely to the good things on the table, and behaved generally so as to induce the idea that he had been drinking. One of the men, however, said he did not believe that the visitor was "a drunken trap," and Curran immediately knocked him down with the butt of his gun. The man jumped up at once and rushed at Curran. There was a struggle for a time, and the man got Curran down. He was, however, too much exhausted to hold him, and Curran got up. The other men, who were all assigned servants on the estate, looked on and applauded the wrestlers, but not one of them made any motion to assist his mate, otherwise Curran might easily have been captured. After his wrestling match Curran walked out of the hut, mounted his horse, and rode away. On the following day Curran again went to the station, and found Mr. North, son-in-law to Major Lockyer, and another man in the store. He called on them to bail up, and both men held their hands up. Curran was about to enter the store-door when he was pinioned from behind. Mr. North and his store-keeper rushed forward, and after a severe struggle, during which the bushranger tried hard to get his gun free, he was captured and tied. The man who had pinioned him was the man with whom he had had the wrestling match the day before. Curran was taken to Goulburn for examination, and was remanded to Berrima to take his trial, "where," said the Port Phillip Herald, "it is to be hoped he will be more securely confined, and not allowed to escape, as he did before."

Paddy Curran and James Berry, another bushranger, were sent to Berrima for trial in charge of Constables McGuire and Wilsmore. They stopped at a hut on the road for a rest and food. After they had finished their meal Constable Wilsmore left the hut, and stayed away for some time. At length Constable McGuire went to the door of the hut to call him, and Berry and Curran, taking advantage of his action, immediately rushed upon him. They were handcuffed together, and this no doubt hampered their movements. McGuire fought hard. The bushrangers had seized the guns, and each held one. McGuire endeavoured to wrest the gun from Curran with one hand, while he held Berry's gun off with the other hand. He yelled for Wilsmore, but Wilsmore did not come. At length Berry got his gun loose and shot McGuire in the back of the head and in the shoulder. At this moment Constable Wilsmore returned, and seeing his mate dead and the prisoners in possession of the guns, ran away again. Curran and Berry beat McGuire about the head until he was dead, and a "fearful spectacle to look upon." Then they searched his body, and finding the key of the handcuffs, released themselves and made off. The two bushrangers continued their depredations for only a few months, however, as they were tracked down by the police and captured. Curran was tried on September 15th, 1841, for the murder of Mr. Fuller. He afterwards confessed to this murder. He said he was in company with two other bushrangers on the road near Bungendore when he heard two men quarrelling. Curran and his mates went towards the road and hid behind trees. Presently two men, riding on one horse, came in sight and appeared to be having a dispute about something. They were talking loud and swearing at each other. Curran stepped out from behind the tree and called on them to stop. Instead of doing so they wheeled the horse and began to gallop away. Curran fired and both men fell, while the horse bolted along the road and soon got out of sight. One of the men jumped up as soon as he fell and ran into the bush and they did not see him again. The other man was Mr. Fuller, and he was either dead or at point of death. "I turned him over and took about £11 in money and a pocket knife out of his pockets," said the bushranger.

Curran was also tried for having committed a rape on Mary Wilsmore. He went to the hut occupied by Wilsmore on the 8th of February. It was near Bungendore. He ordered Mrs. Wilsmore to get him some tea. A bushranger, named White, was with him. Mrs. Wilsmore went outside to get some wood to make up the fire and Curran followed her, knocked her down, and dragged her away to some scrub where he committed the offence. He was found guilty of both crimes and was sentenced to be hung. There were another case of rape, several cases of murder, and numbers of robberies and burglaries charged against him, but none of these were heard.

James Berry was tried for the murder of Constable McGuire, and was sentenced to death.

At the same sessions John Wright, another bushranger, was also sentenced to death. The case against him was as follows;—On May 17th, 1840, Mrs. Margaret Foley, living at Long Swamp, about thirty miles from Bathurst, was going from her house into the detached kitchen at the rear, when three armed men appeared. She shouted "Here's the bushrangers" and ran into the kitchen. Mr. Cunningham, Mr. Foley's partner in the farm, came out of the house and fired both barrels of his gun at the intruders, but failed to hit any of them. The leader of the gang followed Mr. Cunningham, who went back into the house; and saying, "It'll be a long time before you and Steel (son of Captain Steel) hunt us again," shot him dead. Wright then went to the kitchen, pushed the door open, and asked where Foley was? On being informed that he had gone to Bathurst, he replied "I'm sorry for it. I'd 'a served him the same as Cunningham if I'd 'a caught him." He swung his gun about in such a reckless manner that one of the assigned servants in the kitchen requested him to be careful, adding "Recollect that there are women and children here." Wright told him to mind his "own—— business and be——" to him. He continued to swear about Foley's absence and declared that he'd a "good mind to make a clean sweep." He became cooler afterwards, and having collected all the jewellery and other valuables, went away. In passing sentence the Chief Justice commented on the great number of robberies which had been committed by Wright and his gang and said there was no hope of mercy. Wright thanked his Honour and then coolly asked whether he might have a candle in his cell, as it was very dark.