John Winterbottom, born 1789, was a solicitor, town clerk and much respected Mayor of Stockport, Cheshire. He was also a founding partner in Stockport’s first bank.

Banknote with signature of John Winterbottom.

However, in 1839 he faced bankruptcy after a series of failed investments. His desperation led him to defraud a client, the local squire’s widow. As her solicitor he illegally retained the proceeds of a £5,000 insurance policy. When his crime was discovered he went on the run to France, managing to stay at large until 1844, after he returned to see his wife. He was apprehended hiding by a cowshed, exhausted and emaciated. Surprisingly, he pleaded not guilty at the trial, arguing that he had been given legal power over the squire’s estate and that he had always intended to pay the money to the widow. 😎

Nevertheless Winterbottom was found guilty and at the of 57 he was sentenced to transportation for life. This provoked such sympathy that a petition for clemency signed by 20,000 residents of Stockport, Liverpool and Manchester was submitted. It was said that the petition document was 62 yards long. Letters on his behalf were written not only by his wife Lucy, but by his victim in the fraud, Elizabeth Bradshawe-Isherwood. Fortunately Lucy was not destitute, as she had a private income.

Elizabeth Isherwood, defrauded by John Winterbottom.

The court refused to show any leniency. A final plea for the prisoner to be sent to Van Dieman’s Land, where his family could settle, was denied.

Leaving behind his wife and two daughters, Winterbottom was put aboard the convict transport Mayda, bound for that harshest of convict outposts, Norfolk Island. Under the administration of Commandant Joseph Childs the settlement had descended into anarchy, with a gang of hardened prisoners known as ‘The Ring’ virtually doing as they pleased.

Convict ruins on Norfolk Island where John Winterbottom was confined.

The Mayda landed at Norfolk Island on January 8 1846, and the convicts were taken to the seashore to bathe. Despite the presence of constables they were set upon by members of The Ring; beaten and robbed of what few possessions they possessed. It was reported in England that Winterbottom lost £180. Mind you, he was probably the only convict who had any money.

Worse was to follow soon afterwards when the old hands went on a murderous rampage, killing several officials. Thirteen men were publicly hanged. It’s hard to imagine how the genteel, educated Winterbottom coped with it all. One thing in his favour was that he was spared hard labour by being given a job as a clerk. However, life became more difficult for everyone when Childs was replaced by the tyrannical John Price.

Relief for the Mayda convicts came in May 1847, when they were transferred to a probation station in Van Diemen’s Land called Cascades, on the Tasman Peninsula. Here, Winterbottom’s education earned him a position in the prison school, which probably saved his life. My own ancestors, Solomon Shadbolt and his son George, had also been on the Mayda, and Solomon was around the same age as Winterbottom. As barely literate labourers the Shadbolts were involved in felling and hauling timber. The diminutive Solomon (5′ 4″) died from pneumonia during the first winter.

There were further appeals to reduce Winterbottom’s sentence, but although he had wonderful references, even from Commandant John Price, they were unsuccessful.

Cascades Probation Station  where John Winterbottom spent time.

Winterbottom’s behaviour as a prisoner had been exemplary from the start. He duly received his ‘ticket of leave’, essentially allowing him to live and work as a free man, though exiled from England forever. His wife died in 1849, another blow for his daughters and the end of any prospect of a family reunion.

In 1853 he was assigned as a clerk to solicitor Arthur Perry, and subsequently to another solicitor, Frederick Lees, who was also Hobart’s Town Clerk.


On night in February 1857 Winterbottom and his friend Peter Hornsby snatched the hat off a drunken man in Collins Street. It sounded more like a prank than theft, but an officious constable had Winterbottom and Hornsby bought before the court for the theft of the hat, valued at 4/- . They were both sentenced to a month’s hard labour. Frederick Lees was very supportive of his valued employee.

When Lees resigned as Town Clerk a few months later he recommended 68 year old John Winterbottom for the position. The old fellow produced a sheaf of testimonials, including several from England, where his supporters still took an active interest in his welfare.

On Monday last the Municipal Corporation proceeded to the election of a Town Clerk….. There were fifteen applicants for the situation, and among them several solicitors. The election, however, fell upon John Kenyon Winterbottom (late Mayor of Stockport). The choice seems to have given general satisfaction, notwithstanding the disappointed aspirations of the defeated candidates. (The Age, Jul. 29 1857)

However, one of the defeated candidates was an employee of The Daily News, and that publication took great offence on his behalf. They complained about Frederick Lees using his influence to promote Winterbottom who, they argued, did not fulfil the requirement of ‘respectability’. This was a veiled reference to Winterbottom’s convict past and the insurance fraud. For good measure, they suggested the appointment was simply due to some of the aldermen wishing to bask in the glow of having an English ex mayor as their servant. A rival paper hit back;

With regard to the qualification of respectability, on which the Daily News writers so rashly ventures to dilate – with one exceptional circumstance in his life, we hear that Mr Winterbottom has ever borne a most honourable character, He has certainly done so, during his twelve years residence in this colony…..His legal knowledge is unquestionable – he is a good man of business – and the fact of his being recommended by Mr Lees, if such has been the case is surely not to be considered a drawback on Mr Winterbottom’s eligibility. (The Hobart Town Advertiser July 17 1857)

The controversy died down and the new Town Clerk settled into his job, which by all accounts he performed extremely well.

His greatest achievement was managing the administration involved in constructing Hobart’s impressive Town Hall, completed in 1866. John Winterbottom was with the Mayor and Aldermen at the official opening, proudly wearing his official robes.


By the following year the population of Hobart had grown to over 20,000 and it was considered advisable to divide the city into separate wards, with councillors elected in addition to aldermen. This was already the case in Sydney, and Winterbottom wrote to the Town Clerk there for advice on how it all worked.

John Winterbottom was now in his late seventies. At a council meeting in July, a delicate subject was raised; his capacity to continue in the demanding role of Town Clerk. Alderman Lewis sympathized, being of advanced years himself, but he noted;

Their old and friend was now suffering under great infirmity, owing to his advancing years, and long and studious attention to the duties of his office during the past nine years. He thought it would be very much for his benefit if he would now take a short turn of leave of absence…..Alderman Cook said he thought the subject was one which the Council should consider best in the absence of the Town Clerk, and with closed doors. He should therefore suggest that the reporters be requested to retire. (Mercury July 2 1867)

A brief period of leave was hardly going to solve anything, and as the discussion continued in private it was decided to take more drastic action. Mr Winterbottom was to be ‘put out to pasture’ – permanently.

At the meeting of the Town Council of the City of Hobart Town, on Monday the 1st July, it was resolved that in consequence of the infirmity and great age of the Town Clerk, that he be requested to retire, and the council agreed to vote him one years salary, £300, as a token of esteem for his labors of the last ten years. (Tasmanian Times, July 25 1867)

A year’s salary was certainly very generous, but as plans for the old gentleman’s retirement began there was some bombshell news. It was revealed that back in 1865 he had made a grave mistake;

On Saturday the 6th July, it was discovered that Mr John Kenyon Winterbottom, the Town Clerk, had fraudulently re-issued £400 worth of waterworks debentures…He was called on to account for the money, and failing to do so was apprehended, and has since been examined at the Police Office and fully committed for trial for the fraud…Mr Winterbottom is of great age and very infirm, and had been much respected in his office. (Tasmanian Times 25 July 1867)

The distress caused by this indiscretion was intense. Dear me, Mr Winterbottom, what possessed you? 😥

Addressing the elderly prisoner after the jury returned a verdict of ‘guilty’ the Judge said;

John Kenyon Winterbottom, you have been convicted by a jury of your country of embezzling the moneys of your employers, the Hobart Town Corporation. It has been a most painful case – painful to the counsel, both on the part of the Crown and to those who represented you, and painful also, I am convinced, to the jury, who nevertheless were constrained by the evidence to arrive at the conclusion they expressed…..However painful it may be to all concerned, the most painful duty now remains for me to pass upon you the sentence of the law. the pain of having to pronounce on a man in such circumstances such as I shall have to award is no doubt great. But I have a simple duty to perform to society. Unhappily – I know not why – I know not when the temptation came, but you abused the trust and confidence reposed in you. (Sat 14 Sept 1867)

The dilemma for the judge was that, however short the term of incarceration might be, the disgraced Town Clerk was likely to die in gaol, a prospect that horrified everyone.

John Winterbottom

The sentence was two years, with a plea that he given no work that might injure his fragile health.

Against expectations John Winterbottom survived his gaol term, He died on May17 1872 aged 83. What an extraordinary life!


He was certainly a flawed character, but I hope a lot of people turned up at St David’s to farewell him. One report noted that some of his old convict associates were there.

His daughters remained single all their lives. Lucy survived longest, dying in 1919. Subsequently a legal notice was placed in the Hobart papers, mentioning John Winterbottom and his arrival in Tasmania in 1846. There was a worry that he may have left relatives in Tasmania with a claim on his daughter’s estate. However, unlike many convicts, John Winterbottom did not remarry or produce a second family.


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