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The Background
"Jack Donohoe has probably inspired more ballads and legends than any other bushranger, Ned Kelly excepted," Bill Wannan writes in his 1963 book Tell 'Em I Died Game. "In his own time, and up to the 1850s, he was looked upon by the respectable colonists as 'the bloodiest malefactor that ever broke bonds'. But in the songs of the people he was elevated to the status of a folk hero."
Bold Jack Donohoe has been collected very widely, not only in 1950s Australia, but in England, Ireland, Canada and the USA long before that. One notable example is preserved on an Irish ballad sheet called The Adventures of Jack O'Donohoe, dated to around 1870, which uses very similar lyrics to those below. "Whether BJD was written in Australia or written by someone in Britain, we don't know," the Aussie folklorist Keith McKenry told me. "It was never published in Australia that we can find, but it certainly was published all over the British Isles."
The lyrics here - which I've taken from Wannan's book - are said by bushranger expert Bill Scott to give the song in its earliest known and most factually-reliable version. "The form follows closely the broadsheets and ballads sold in the streets of England and Ireland," Scott points out. "The first line is almost the set beginning for a highwayman ballad". ^{(1, 2)}

The Ballad
'Twas of a valiant highwayman and outlaw of disdain,
Who'd scorn to live in slavery or wear a convict's chain,
His name, it was Jack Donohoe, of courage and renown,
He'd scorn to live in slavery or humble to the Crown.

This bold, undaunted highwayman, as you may understand,
Was banished for his natural life from Erin's happy land,
In Dublin, city of renown, where his first breath he drew,
It's there they titled him the brave and bold Jack Donohoe.

He scarce had been a twelve-month on the Australian shore,
When he took to the highway, as oft he had before,
Brave McNamara, Underwood, Webber and Walmsley too,
These were the four associates of Bold Jack Donohoe.

As Jack and his companions roved out one afternoon,
Not thinking that the pains of death would overcome so soon,
To their surprise, five horse police appeared all to their view,
And in quick time they did advance to take Jack Donohoe.

"Come, come, you cowardly rascals, oh do not run away,
We'll fight them man to man, my boys, their number's only three,
For I'd rather range the bush around, like dingo or kangaroo,
Than work one hour for government," said Bold Jack Donohoe.

"Oh no,' said cowardly Walmsley, "to that I won't agree,
I see they're still advancing us - their number's more than three,
And if we wait we'll be too late, the battle we will rue,"
"Then begone from me, you cowardly dog," replied Jack Donohoe.

The sergeant of the horse police discharged his car-a-bine,
And called ahead to Donohoe, "Will you fight or resign?"
"Resign? No, no. I never will, unto your cowardly crew,
Today I'll fight with all my might," cried Bold Jack Donohoe.

The sergeant then, he hurried his party to divide,
Placed one to fire in front of him, another on each side,
The sergeant and the corporal, they both fired too,
Till the fatal ball had pierced the heart of Bold Jack Donohoe.

Six rounds he fought those horse police before the fatal ball,
Which pierced his heart with cruel smart, caused Donohoe to fall,
And as he closed his mournful eyes, he bade this world adieu,
Saying, "Good people all, pray for the soul of poor Jack Donohoe."

There was Freincy, Grant, bold Robin Hood, Brennan and O'Hare,
With Donohoe, this highwayman, none of them could compare,
But now he's gone to Heaven I hope, with saints and angels too,
May the Lord have mercy on the soul of brave Jack Donohoe.

The Facts
Donohoe was born in Dublin in 1806 0r 1807, and seems to have spent most of his teenage years getting in trouble with the police. In 1824, at the age of 18, he was found guilty of intent to commit a felony and sentenced to transportation for life.
"Records do not disclose the exact nature of the offence contemplated by Donohoe, but it was possibly of a political nature," John Meredith writes in his 1960 biography of the man. "He had grown up in the stress of economic depression and political repression that followed the risings of 1798 in Ireland." Another Donohoe ballad suggests he was a member of Wolfe Tone's revolutionary movement, the Society of United Irishman. "For being a bold United boy / I was forced to cross the main," Donohoe declares in that song. ^{(3, 4)}
His convict ship reached Sydney Cove in January 1825, and Donohoe was assigned to work as an unpaid farm labourer for a Mr Pagan at Parramatta. "His rebellious nature would not allow him to accept his lot with resignation," Wannan writes, "For some infraction of discipline, he was put into a road gang at Vinegar Hill. There, it was officially hoped, the brashness would be taken out of him."
Some hope. The next we hear of Donohoe is in December 1827, when he's tending pigs at Quakers Hill for a farm owner called Major West. That's where he met William Smith and George Kilroy, two other convict labourers, and the three men decided to try their luck robbing the slow-moving bullock carts which were then the colony's main transport.

One of the men they robbed was George Plomer, whose ordeal that day was reported in the Sydney Gazette: "[Plomer] was proceeding along the road from Sydney to Richmond in a cart, in company with two other persons who also had carts, when three men rushed out of the bush. Two of them, the prisoners Kilroy and Smith, were armed, the one with a pair of horse pistols, the other with a cutlass.
"Kilroy and Smith rushed towards the witness and demanded his money. He gave them four shillings. The prisoner Donohoe, who appeared to have been engaged with the other two carts, then came forward, got into the witness's cart and took thereout a keg, containing five gallons of brandy." ⁽⁵⁾
One of the other carters in the party was George Brown, who accompanied police round all the nearby farms looking for the culprits among their convict workers. That's how they found Kilroy, who promptly shopped Donohoe and Smith as his two accomplices. All three men were found guilty of highway robbery - both the Plomer incident and another hold-up they'd staged the same day - and sentenced to hang. ⁽⁶⁾
"The learned judge pronounced the death sentence, warning the unhappy men not to entertain any hopes of mercy," Meredith writes. "Donohoe decided he had nothing to lose, but life and liberty to gain. When the batch of prisoners from the court was returned to the gaol, he was missing. That he was able to escape while heavily ironed and under a numerous guard caused a sensation among the townsfolk of Sydney." ⁽⁷⁾
This was the first escapade that made Donohoe famous, and it set the template for everything that followed. Here was a man who seemed able to make fools of the police and colonial authorities with contemptuous ease, and one who promised to supply the newspapers with a great deal of highly entertaining copy. It wasn't long before his escape was being cheered by the balladeers too:

Now, Donohoe was taken, all for a notorious crime,
And sentenced to be hanged upon the gallows tree so high,
But when they came to Sydney gaol, he left them in a stew,
And when they came to call the roll they missed bold Donohoe.

As Donohoe made his escape, to the bush he went straightway,
The people, they were all afraid to travel night or day,
For every week the newspapers would publish something new,
About this dauntless hero, the bold Jack Donohoe. ⁽⁸⁾

The colonial authorities put a £20 bounty on Donohoe's head (equivalent to a rural labourer's annual wage), but had no takers. He resurfaced in August 1828, about five months after his escape, as part of a nine-strong gang raiding settlers' huts in the pioneer territory south of Bathurst. One of their targets was a supply store owned by three brothers named James, Samuel and Jonathan Hassall, who told the Sydney Gazette what happened:
"Seven shots were exchanged between the men [manning the stores] and the robbers," they said. "Three men were inside the house, firing upon the thieves who, to save themselves, placed the rest of our men before the door outside and told them to shoot their own men. [.] The three men inside were stripped naked in order to be shot, but were spared by the captain of the banditti." We don't know whether or not Donohoe was heading the gang at this point, but it is clear he was the most famous member. To the Hassalls, he's already "the most notorious Donohoe".
The thieves escaped with a haul that included clothes, food, tobacco, weapons and a couple of horses. A party of six policemen and their aborigine trackers was sent from Bathurst to find and arrest them, accompanied by James Hassall and a man called Walker. Four days later, they found the gang playing cards round their cooking fire and moved in.
"As soon as [the bushrangers] saw the police, they dispersed to protective positions," Wannan writes. "With shouts of 'Ha-hoo! Come on now, we are all ready!', they peppered their adversaries with shot. Several bushrangers were wounded and one was killed. The others escaped during the night, but were shot dead or recaptured one by one until only Donohoe was left unaccounted for. The police and black trackers almost caught him but, with his usual mixture of skill and luck, he eluded them and vanished from their sight."
After a brief partnership with an Irish labourer called William Underwood, Donohoe teamed up with Jack Walmsley, an escaped convict like himself, to work the Nepean Valley around Penrith. Part of what they did there was simple highway robbery in the classic Dick Turpin style. Donohoe's network of convict workers in the area ensured he always knew just when his chosen victims would be on the road, and which ones were likely to be carrying the most valuables. Often, their behaviour proved difficult to square with the romantic view of bushrangers as lovable rogues.
On March 26, 1829, Donohoe and Walmsley held up a settler called William Clements on the road near Windsor. "[He] was stopped by two armed men, one of whom, as Mr Clements was about to draw a pistol from his side, fired at and killed him on the spot," April 2's Sydney Gazette reported. "The robbers then plundered him of what property he had on his person, part of which consisted of a silver watch of his own and a gold one, belonging to a Mr Liddle of Hunter's River, which he was bringing to Sydney to be repaired."
A couple of weeks later, the Sydney Monitor added some detail, saying the robbers had demanded tobacco. Clements, hoping they'd think that's what he was looking for, felt in his pocket for the pistol. "The ruffian, suspecting Mr Clements' intention by his manner, stepped up to him and shot him in the forehead," the Monitor reported. "Mr Clements was left in a dying state on the road for anybody to pick up that passed that way." ⁽⁹⁾

It's unclear whether it was Donohoe or Walmsley who pulled the trigger that day - although most of the suspicion seems to fall on Walmsley. Clements, it turned out, had been responsible for overseeing the convict workforce at a Hunter's River farm, and some think Walmsley killed him in revenge for the cruel treatment he'd suffered there. Another theory is that Walmsley was appalled to see their victim was someone who could identify him from his Hunter's River days, and shot him simply to avoid that happening.
Six months later, the two men raided a cottage at Sir John Jamison's Regentville estate. They easily overcame the two elderly men they found caring for a child inside, whose names were Hoe and Dunn. They tied their captives up back-to-back, forced a great deal of rum down the two men's throats, and set about preparing themselves a meal. "The robbers then baked a cake and fried enough pork for their supper," the Sydney Gazette reported. "After regaling themselves, the low squat man piled wood on the fire until the blaze was nearly reaching the thatch, when old Hoe entreated them not to burn them alive.
"This caused the tallest of the robbers to find fault with the cruel intention of the other, and with a bucket of water he quenched the flame which otherwise, in a few minutes, would have consumed the house, the old men lashed together and the boy asleep in his bed. The tall robber, who appeared to be an Englishman, found fault with the unmerciful disposition of the squat, flaxen-haired robber, who spoke broad Irish and blasphemed, with murderous threats in all his actions." ⁽¹⁰⁾
We know from descriptions printed in the Sydney Gazette that Walmsley was a couple of inches taller than Donohoe (5' 5" against Donohoe's 5' 3") and his surname supports the paper's conclusion that he was English. All the evidence, therefore, points to Donohoe here being the one willing to burn three innocent people alive, and Walmsley stepping in to stop him. ⁽¹¹⁾
In the early months of 1830, a man called Bill Webber joined Donohoe and Walmsley's gang, bringing a new talent for planning more ambitious and elaborate crimes. Fortunately for the balladeers, not all their escapades had such a grim tone as the Regentville fire episode. Meredith details a dozen or more raids where the gang emerge as much more charming figures. Here's just a few examples:

* The raid on Captain Sturt. Sturt was an English explorer who'd come to Australia in 1827 and won considerable fame for his expeditions into its unknown interior. One day in 1830, Donohoe and his gang strode up to Sturt's Varroville farm intending to rob it. "As soon as 'Bold Jack' knew who the farmer was, he said to his accomplices, 'Stand back, boys! It's Captain Sturt and we don't rob him'," Wannan reports. "He told Sturt he would never raise his gun against him; but he challenged him, as a magistrate to do his damnedest [to capture the gang]."

* The dandy highwaymen. Several of the gang's victims told police how dapper their assailants had been. William Boyle, who they robbed on August 19, 1830, gave this detailed description of Donohoe's clothes: "Black hat, superfine blue cloth coat, lined with silk surtout fashion, plaited white shirt (good quality), laced boots rather worn at the toes and snuff coloured trousers".

* Impersonating the police. James Hassall was travelling to Sydney one morning when he saw what appeared to be an armed policeman with two manacled prisoners coming the other way. When they drew level, the two "prisoners" dropped their unfastened chains to the ground and the "policeman" levelled his gun at Hassall and his passenger, demanding their belongings. They got away with £15. ⁽¹²⁾

* Your trousers or your life. A month earlier, while robbing a Mr Campbell, Donohoe had insisted on swapping trousers with him. "He was rather facietious during the performance of this operation," one newspaper noted.

* Locking up the police. One night in Parramatta, two constables named Brown and Hamilton challenged a suspicious figure loitering outside the court house. As they did so, two other men appeared behind them, stuck pistols in their backs and then locked them in the courthouse yard. No one doubted that the three men responsible had been Donohoe, Walmsley and Webber.

The newspapers were now running increasingly furious articles berating the authorities for their failure to bring Donohoe and the other bushrangers to heel. "The bushranging gentry were never so daring as they are now," The Australian raged. "Why is not an effective patrol at once sent in quest of these ruffians?"
Governor Darling responded by raising the bounty on Donohoe's head to first £50, then £75 and finally £150, throwing in the promise of a full pardon and free passage to England for any convict who helped to kill or capture him. Free men would get not just the cash, but a square mile of free land too. The assumption was that Donohoe's two companions must still be John MacNamara and William Underwood, so the same reward was offered on each of them. ⁽¹³⁾
There were sweeping new powers for the police, giving them licence to arrest suspected bushrangers on grounds of that suspicion alone and to enter and search anyone's premises at will. This just made the police more unpopular than ever with honest settlers, intensifying their determination to help out the bushrangers all they could. A new tactic of police disguising themselves as bushrangers led to several incognito cops being shot - some by travellers who feared they were about to be robbed and others by their own police colleagues. ⁽¹⁴⁾
Still Donohoe remained at large. Two of the cops most determined to catch him were John Thorne, the chief constable at Parramatta, and Samuel Horn, one of his men. In June 1830, just a few days after the reward on MacNamara's head had been posted, the pair tracked him down on the Windsor Road and shot him dead. Most accounts credit Thorne with firing the fatal shot, and all agree he was the one who got the cash and land in reward. ⁽¹⁵⁾
Thorne and Horn were called in again on July 23, 1830, after the three outlaws ran into some troopers on a Mr Riley's estate in Raby. A gun battle broke out, wounding Donohoe and forcing him to flee with the rest of the gang. Mounted police tracked a trail of blood from Donohoe's wound, finding two fowling pieces and a pistol the bushrangers had been forced to abandon as they fled. About a quarter mile on from that spot, there was a large pool of blood and signs that a wound had recently been dressed nearby.
Joining the hunt next day, Thorne and Horn discovered a couple of crude bark huts and a hollow tree, which they concluded Donohoe and his mates had been using for shelter. There was no sign of the men themselves, but this was progress all the same. Bold Jack Donohoe was entering his final act.

Donohoe's end came on September 1, 1830, when he was trapped by a group of police on the Wentworth farm near Bringelly in New South Wales. Constable Michael Gorman described the events of that day at Donohoe's inquest five days later. He was part of nine-strong team of cops and soldiers, six of them on horseback, who'd been in the bush for the past two weeks looking for Donohoe, Walmsley and Webber. At five o'clock that evening, they spotted three men with a pack horse about a mile and a half away and gave chase. Here's an extract from Gorman's testimony:
"The bushrangers were at this time near the bank of a creek and, to avoid losing them if they crossed, we separated. The sergeant and two men proceeded along the left side, while myself and the others went cautiously to the right. We got to within a hundred yards of them without their seeing us. Then, suddenly espying us, they prepared to defend themselves and Donohoe shouted, 'Come on, you cowardly rascals! We're ready if there's a dozen of you!' The bushrangers then each got behind a tree, and a discussion of some length followed about fighting."
Private John Muckleston, another member of the police party, added his own testimony. "When called upon to surrender, [Donohoe] took off his hat, waved it three times, and threw it in the air," Muckleston said. "He shouted, 'Come on, you bloody bastards. We're ready of there's a dozen of you!" And here's Gorman again:
"After a lapse of nearly half an hour, one of the policemen fired, his shot, knocking the bark from the tree that Webber was standing behind. I now levelled my piece, which went off at the same moment as those fired by two of the robbers. In about another minute, one of the soldiers named Muckleston fired, and I instantly saw Donohoe fall." ⁽¹⁶)
Seeing which way the battle was going, Walmsley and Webber fled. The police and soldiers chased after them until dark, but then had to give up. "When we returned to Donohoe, he was in his last agonies," Sergeant William Hodson told the inquest. "One ball had entered his neck and the other his forehead - Private Muckleston having loaded his carbine with [both] a carbine ball and a pistol ball." ⁽¹⁷⁾

Hodson took Donohoe's body to Sydney Hospital, where it was formally identified and a death mask taken of his face. Thomas Mitchell, Governor Darling's surveyor general, sketched Donohoe's body on the mortuary slab and added a caption from Byron's narrative poem Mazeppa: "No matter; I have bared my brow / Full in Death's face - before - and now". The inquest was held on September 6, at a Sydney pub called The Fox & Hounds, where the coroner's jury took just five minutes to pronounce Donohoe's death a justifiable homicide.
The colonial authorities heaved a sigh of relief as they buried Donohoe, but there was no doubt the common people were still on his side. Just after the inquest, an enterprising Sydney tradesman started selling clay pipes with a bowl in the likeness of Bold Jack's head - bullet hole and all. He did a brisk trade. "They were snapped up as devotional effigies," Robert Hughes writes in his 1988 book The Fatal Shore. "Ceramic ballads, as it were." ⁽¹⁸⁾

The Music
The artists who've recorded Bold Jack Donohoe include Warren Fahey, Fotheringay, AL Lloyd, The New Lost City Ramblers Gary Shearston and Matt Walker. No doubt there are many others. You can hear the Fahey, Lloyd and Walker versions on the Spotify playlist I've called PlanetSlade Bushrangers.

Sources & footnotes
1. Tell 'Em I Died Game: The Stark Story of Australian Bushranging, by Bill Wannan (Currey O'Neil, 1963).
2. Bushranger Ballads, by Bill Scott (Lansdowne Press, 1976).
3. The Wild Colonial Boy: The Life & Times of Jack Donohoe, by John Meredith (Wentworth Press, 1960).
4. The "United boy" lyrics here are quoted in Meredith (above) and attributed to an old Irish version of the ballad.
5. Sydney Gazette, February 6, 1828.
6. "Kilroy [hoped] to escape the gallows by treachery, and by placing his companions thereon," The Australian reported three years later. "But some of the parties who had been robbed could perfectly identify all three of them, and Kilroy was therefore disappointed."
7. Smith and Kilroy went to the gallows with a convicted murderer called William Johnson, the idea being to hang all three of them at the same time. But things did not go according to plan. When the drop was pulled Smith's rope broke, leaving him to fall through the trap door to the ground beneath. "He was uninjured, but distraught with fear at the sight of his companions swinging overhead," Meredith writes. "Smith had to wait until the other two bodies had hung for the prescribed time before the drop could be readjusted. His sentence was then carried out."
8. I've taken these verses from Wannan (above), who includes several different versions of the ballad in his book.
9. Sydney Monitor, April 18, 1829.
10. Sydney Gazette, September 24, 1829.
11. This incident echoes a robbery Donohoe had carried out with Underwood a year earlier. A man called Faithful told the Sydney Gazette he'd been stopped on the road by a tall man and his shorter companion, the first of whom held Faithful's horse while the other climbed up to search the cart. Searching Faithful's waistcoat, the short man found a penknife which the young man begged him not to take, as it had been a gift from his uncle. "He first put it in his pocket," Faithful explained. "On my asking for it again, the fellow at the horse's head told the other to give it back, which he did." Meredith concludes that Underwood here "acted as leader and exercised a restraining influence on the impetuous Donohoe". Walmsley seems to have inherited that role.
12. This is the same James Hassall whose family's storehouse Donohoe had robbed in August 1828. The Hassall brothers had a reputation for treating their convict labourers with great cruelty, which may be why Donohoe targeted them so often.
13. MacNamara was certainly a bushranger - he'd come over from County Cork on the convict ship Isabella in 1823 - but why he's so persistently associated Donohoe, I don't know. The idea always seems to be that he was an early member of Donohoe's gang, but left long before 1830.
14. Stephen Knight, writing in the Sydney Morning Herald of November 27, 1982, calls this network of fences, lookouts and spies "the sea in which Donohoe and his partners swam, like the western suburbs' Vietcong."
15. One dissenting voice came in a 2016 account from Sydney's Daily Telegraph, which claims it was actually Horn who killed MacNamara. It adds that he was given half a square mile of free land, which sounds suspiciously like a bribe to ensure he never disputed Thorne's claim.
16. Reverend James Hassall (that family again) gave his own account of Donohoe's death in a 1902 memoir called In Old Australia. "The convict ran behind a tree so that, for some time, it was impossible to get a shot at him," he writes. "After a while, the trooper suddenly flung his cap on the ground at the side of the tree. When the bushranger, fancying it was a step that he heard, looked out from his shelter, he received a ball in his temple." How reliable this version is, I don't know.
17. Walmsley and Webber were both captured in 1831 and Webber hanged in July of that year. Walmsley saved his own neck from the rope only by informing on the gang's network of fences and customers. "His revelations caused quite a sensation, a number of hitherto highly-respected persons being implicated," George Boxall writes in his 1976 History of Australian Bushrangers. Perhaps it's Walmsley's decision to grass which explains why he's explicitly condemned as a coward in the song, but Webber is not.
18. Donohoe also inspired the first play written and published in Australia by an Australian. Charles Harpur wrote The Tragedy of Donohoe in 1833, when he was just 20 years old.