Squire ran a number of successful ventures during his life, including a farm, a popular tavern called The Malting Shovel, a bakery, a butcher shop and a credit union.

As a testament to the rise of position in society (from shame to fame), his death in 1822 was marked with the biggest funeral ever held in the colony.

Their families had been embroiled in a dramatic incident (the Canning affair) which polarised England in 1754, the year of Squire's birth.

[5][a] In 1774, when Squire fled a ransacked house, he ran straight into several members of the local constabulary and was arrested for highway robbery.

Squire stole five hens and four cocks and diverse other goods and chattels from John Stacey's yard, just when the British Government needed people for the transported convict program.

On 11 April 1785, he was sentenced to join the First Fleet at the General Sessions of the Peace for the Town & Hundred of Kingston upon Thames, England.

[8] Mary gave birth to a son, who was named Francis (born and baptised on 1 August 1790 on Norfolk Island[8]).

The openness of this bay, and the dampness of the soil, by which the people would probably be rendered unhealthy, had already determined the Governor to seek another situation.

He resolved, therefore, to examine Port Jackson, a bay mentioned by Captain James Cook as immediately to the north of this.

These medicines were, in fact, one pound of pepper (or paper) and horehound (a herb that imitates the tangy flavour of hops), belonging to surgeon John White.

Though Squire claimed the stolen horehound was for his pregnant girlfriend, he later revealed at the Bigge inquiry that he began brewing beer on his arrival to Australia, which he sold for 4d per quart.

His sentence of 14 November 1789 read: "one hundred and fifty (lashes of the whip) now, and the remainder when able to bear it".19 August 1791, Squire and another man were fined £5 each for buying the necessaries of a private.

On emancipation James was granted 30 acres (0.12 km2) at Eastern Farms (Kissing Point) on 22 July 1795,[17] and he noticed other emancipists had not claimed the nearby land.

Displaying his resourcefulness, James marched them into the Colonial Secretary's office (position held by David Collins) to claim their land grants, and then purchased each property for one shilling.

James stated at the Bigge inquiry into New South Wales and Van Diemen's Land in 1820 that he had been brewing for 30 years and that he made it from hops he got from the Daedalus.

This created an uproar in the fledgling colony and Governor King was gravely concerned about the corruption spread by rum, so he began to officially endorse the brewing of beer.

On 11 March 1806 James Squire attended Government House with two vines of hops taken from his own grounds.

Governor King was so pleased with the flavour and quality that he: "directed a cow to be given to Mr Squire from the Government herd".

He then worked in a credit union style of banking and was widely known for his fair play as a lender and a philanthropist to his poorer neighbours.

At this meeting, James (among others, including Simeon Lord) obtained the judge's permission to be licensed for the sale of spirituous liquors at The Malting Shovel.

Unfortunately a lot of this information is missing, but the Sydney Gazette and the State Records Authority of New South Wales fill in a number of gaps with evidence of licence renewals on the following dates: James Squire died on 16 May 1822.

The article from the Sydney Gazette stated: Deaths: – On Thursday evening last, at Kissing Point, after an illness of about 3 months, Mr James Squire, in his 68th year.

The "OLD HANDS",[c] by the frequent visitation of death, are becoming thinned in their ranks; this should lead to reflection, for the day will soon arrive when even those, now living, shall cease to say, "I came in the first fleet.

From 1823, Squire's brewery continued to successfully operate under control of his son James, producing about 100,000 gallons a year, until his death in 1826.