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The Top Dollars. Emulating Philip Spalding’s famous 'Top Dollars’ (1973), Coinworks presents an updated version.


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In the realm of rare coins, Holey Dollars exist on a different plane.

They transcend mere collectibles, and have become coveted objects that represent the pinnacle of Australia's numismatic industry, our very first coin.

Owning a Holey Dollar isn't just about adding another coin to a collection. It's about indulging in an experience, a fusion of history and prestige.

You are not just buying a coin, you own the experience.


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Ferdinand VI

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Charles III

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Charles III Deceased

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Charles III on Charles IV

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Charles IV

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Charles IV Continental

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Ferdinand VII

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Ferdinand VII Hannibal Head


This article presents the 'Top Dollars'. They are exceptional coins. Some are unique. All are rare. 

Eight Holey Dollars have been selected to represent the Spanish monarchs of Ferdinand VI, Charles III, Charles IV and Ferdinand VII and are shown above. They are the finest available.

Four Holey Dollars have been selected to represent the issuing mints, the Madrid Mint and the Spanish colonial mints of Mexico, Lima and Peru and are shown below. They too are the finest available.

Each coin is a benchmark of its type, a standard of excellence against which others are judged. 

They are absolutely, the 'Top Dollars'.

This article will leave you in no doubt that with less than two hundred available to collectors, all Holey Dollars are rare. 

So how to capture the magnitude of the 'Top Dollars' featured in this article?

They are unequivocally, the rarest of the rare. 


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Madrid Mint

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Mexico Mint

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Potosi Mint

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Lima Mint


When you look closely at the Holey Dollars shown above, each coin has a different date and the legend and portraits, can vary.

Put them together and they tell a story. Their narrative, is as much about Australian history as it is about European history, charting the changing Spanish monarchs, Ferdinand VI, Charles III, Charles IV and Ferdinand VII. And reflecting the associated political and social turmoil that so often occurs when a monarch dies or abdicates. 

Now, look closely again at the Holey Dollars shown above, and you will notice that the counter stamps, New South Wales, 1813 and Five Shillings applied discretely around the edge of the hole are not uniformly positioned. And there is no consistency as to which side of the coin they appear on.

As to why there are different dates and monarchs appearing on the Holey Dollars? 

The simple answer is that the Holey Dollar was not created from a silver blank onto which a decorative pattern was stamped in a mass production process that produced thousands of uniformly struck coins, each featuring the same design. The Holey Dollar was created from another coin, a Spanish Silver Dollar.

Forty thousand Spanish Silver Dollars were imported by Governor Lachlan Macquarie from the East India Company to convert into forty thousand Holey Dollars, the nation's first circulating currency. And each coin was different.

The order for the dollars was not date specific, any date would suffice. And as the dates changed, so could the monarchs, Charles III, Charles IV, Ferdinand VI or Ferdinand VII. And the coins were struck at various mints around the world. As the Spanish colonies were prolific producers of silver dollars, the majority originated in Mexico, Peru or Bolivia. Some also originated in Spain. 

Macquarie did not set any quality parameters on his shipment of 40,000 coins and the quality of each coin varied. The Spanish Silver Dollar was the coin that 'ruled the world' in the eighteenth century, internationally traded. Most of the dollars imported by Macquarie were well used, their design details worn to the point of being partially obliterated.

As a consequence most Holey Dollars are today found well worn.

As to why the counter stamps are in different positions and on different sides of the coin? 

The counter stamps are important as technically the application of the counter stamps, New South Wales, 1813, and Five Shillings was the point at which the holed Spanish coin became the 1813 Holey Dollar, the nation's first locally made coinage. Worn counter stamps equates to extensive usage of the Holey Dollar. 

A study of the surviving Holey Dollars reveals that Henshall's application of the counter stamps was wildly random, that the holed dollar was not placed in a particular position between the dies. And it obviously didn't matter which side of the holed dollar was facing up.

The process used a simple drop hammer system and speed was of the essence. Precision was simply not required which is why the counter-stamps of most Holey Dollars are 'all over the shop'.

The miracle state of the 'Top Dollars' shown above is re-affirmed when you compare them to the average examples shown here. Note the wear on the original Spanish dollars and the wear to the counter stamps.

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Charles IV • 1805
Well circulated

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Charles IV • 1805
Worn counter stamps

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Ferdinand VII • 1809
Well circulated

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Ferdinand VII • 1809
Obliterated counter stamps



Holey Dollars representing the monarchs Ferdinand VI, Charles III, Charles IV and Ferdinand VII, and each the finest of their type.

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The Pillar Dollar

The finest, and the earliest, of only two Holey Dollars that were created from a Spanish Dollar of the 'pillar' type, issued during the reign of Ferdinand VI.

No examples are held in institutions worldwide. 

Date of the silver dollar: 1757

Reigning monarch: Ferdinand VI (1746 - 1759)

Design of the silver dollar: pillar type

Portrait: no portrait, the reverse features two classically styled pillars

Legend: Ferdinand VI (on the reverse)

Quality of the silver dollar : About Fine 

Quality counter stamps: About Fine

Exhibited: Macquarie Bank 2013, Royal Australian Mint 2019

Value $500,000+


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The Montague '1788' Holey Dollar

Created from a Spanish Silver Dollar of the 'bust' type depicting the portrait and legend of Charles III. This coin is the finest of twenty four Charles III Holey Dollars. 

The quality of the Spanish Silver Dollar is amazing when you consider that it was minted in 1788 and had twenty five years of circulation before it was converted into a Holey Dollar in 1813. We also note that the counter stamps, applied by William Henshall around the edge of the hole are vertically aligned on both obverse and reverse. This is the optimum position of the counter stamps and was rarely ever achieved. Given the date of 1788, and its precise counter stamps, there is some suggestion that the coin may have been especially struck.

Date of the silver dollar: 1788

Reigning monarch: Charles III (1759 - 1788)

Design of the silver dollar: colonial bust type

Portrait: Charles III

Legend: Carolus (Charles) III

Quality of the silver dollar : About Extremely Fine

Quality counter stamps: Extremely Fine

Exhibited: Macquarie Bank 2013, Royal Australian Mint 2019

Value $500,000+


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The Charles III (deceased) Holey Dollar

Created from a Spanish Silver Dollar of the 'bust' type depicting the portrait and legend of the deceased King Charles III (Charles III died in December 1788). To maintain coin production, the colonial mints continued to produce coinage with the legend and portrait of the deceased king. 

This Holey Dollar was converted from a silver dollar minted in Peru. It is unique. Again, we comment on its superior quality for the dollar circulated twenty four years before it was converted into this Holey Dollar in 1813. Amazing!

Date of the silver dollar: 1789

Reigning monarch: Charles IV (1788 - 1808)

Design of the silver dollar: colonial bust type

Portrait: Charles III

Legend: Carolus (Charles) III

Quality of the silver dollar : Extremely Fine

Quality counter stamps: Extremely Fine

Exhibited: Macquarie Bank 2013, Royal Australian Mint 2019

Value $550,000+


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The Charles III on Charles IV Holey Dollar

To ensure that the colonial mints could continue their coinage production uninterrupted, a Royal decree granted them the right to amend the legend to Carolus IV to acknowledge the new monarch but continue striking coins with the portrait of the deceased King Charles III. 

This coin is the finest of eight privately held examples depicting the portrait of Charles III and the legend Carolus IV.

Date of the silver dollar: 1790

Reigning monarch: Charles IV (1788 - 1808)

Design of the silver dollar: colonial bust type

Portrait: Charles III

Legend: Carolus (Charles) IV

Quality of silver dollar : About Extremely Fine

Quality counter stamps: Extremely Fine

Exhibited: Macquarie Bank 2013, Royal Australian Mint 2019

Value $400,000+


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The Unique Charles IV Holey Dollar

This Holey Dollar is without peer. A Holey Dollar created from a Spanish Silver Dollar that shows no signs of circulation. It begs the question ... as the original silver dollar was minted in Mexico in 1805, how did it avoid usage in the seven years before it arrived in the colony of New South Wales? And how did it avoid usage after it was converted into a Holey Dollar in 1813? 

Miraculous preservation, unique for quality, and the absolute finest of the three hundred Holey Dollars that are held in private collections and institutions, worldwide. 

Date of the silver dollar: 1805

Reigning monarch: Charles IV (1788 - 1808)

Design of the silver dollar: colonial bust type

Portrait: Charles IV

Legend: Carolus (Charles) IIII

Quality of silver dollar : Uncirculated

Quality counter stamps: Uncirculated

Value $600,000+


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The Madrid (Continental) Holey Dollar

Created from a Spanish Silver Dollar of the 'bust' type that was minted at the Madrid Mint. The Spanish Mints of Madrid and Seville produced silver dollars of a different design to those minted in the colonies and are referred to as Continental dollars. They were a status of Royalty, the Church and wealthy landowners and were as a consequence hoarded. Holey Dollars converted from Continental dollars are by default, exceedingly scarce. 

This is the finest of six Continental Holey Dollars (two Seville Mint and four Madrid Mint) and the only one in private hands. Noted in 1988 as 'the most desirable' of all Holey Dollars.

Date of the silver dollar: 1802

Reigning monarch: Charles IV (1788 - 1808)

Design of the silver dollar: continental bust type 

Portrait: Charles IV

Legend: Carolus (Charles) IIII

Quality of the silver dollar : Good Extremely Fine

Quality counter stamps: Good Extremely Fine

Exhibited: Macquarie Bank 2013, Royal Australian Mint 2019

Value $675,000+


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The Ferdinand VII Holey Dollar

Created from a Spanish Silver Dollar of the 'bust' type depicting the portrait and legend of Ferdinand VII. In 1808, Charles IV abdicated the throne for his son Ferdinand VII. In that same year, Napoleon Bonaparte persuaded Ferdinand to relinquish his monarchical authority. He, in turn, placed his brother Joseph Bonaparte on the Spanish throne. The colonial Mexico Mint refused to accept Bonaparte as king and continued to use the portrait and legend of Ferdinand VII. 

This coin is the finest of thirteen Holey Dollars featuring the legend and portrait of Ferdinand VII.

Date of the silver dollar: 1809

Reigning monarch: Joseph Bonaparte (1808 - 1813)

Design of the silver dollar: colonial bust type

Portrait: Ferdinand VII

Legend: Ferdinand VII

Quality of silver dollar : Extremely Fine

Quality counter stamps: Extremely Fine

Exhibited: Macquarie Bank 2013, Royal Australian Mint 2019

Value $500,000+


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• Pencil illustration Numismatic Chronicle London 1883 •

The Hannibal Head Holey Dollar

Created from a Spanish Silver Dollar of the 'bust' type depicting the legend of Ferdinand VII and an imaginary portrait referred to as the 'Hannibal Head'. In 1808, Charles IV abdicated the throne for his son Ferdinand VII. In that same year, Napoleon Bonaparte persuaded Ferdinand to to relinquish his monarchical authority. He, in turn, placed his brother Joseph Bonaparte on the Spanish throne. The colonial mint in Lima Peru also refused to accept Bonaparte as king and maintained the legend Ferdinand VII. In an even stronger political protest, the Lima Mint introduced a new portrait of the monarch to its dollars - said to be most unflattering -  referred to as the 'Hannibal Head'. 

This coin is the finest of two Hannibal Head Holey Dollars and is the most historic of the nation’s Holey Dollars. Its discovery was written up in the Hobart Mercury (1883) and the Sydney Morning Herald (1884). Furthermore, a pencil drawing of this coin, published in 1883 in London's Numismatic Chronicle, is the earliest known illustration of Australia’s very first coin (shown here). 

Date of the silver dollar: 1810

Reigning monarch: Joseph Bonaparte (1808 - 1813)

Design of the silver dollar: colonial bust type

Portrait: imaginary, known as the Hannibal Head

Legend: Ferdinand VII

Quality of silver dollar: About Extremely Fine

Quality counter stamps: Extremely Fine

Exhibited: Macquarie Bank 2013, Royal Australian Mint 2019

Value $550,000+


Holey Dollars representing the Madrid Mint and colonial mints of Mexico, Lima and Peru and each the finest of their type (the mint mark circled).

Macquarie’s shipment of Spanish Silver Dollars was ordered from the East India Company and came from Madras. 

It was comprised of coins struck in Spain with the overwhelming majority coming from the Spanish colonies of Mexico, Peru, Bolivia and Guatemala.

Holey Dollars created from silver dollars sourced from the Mexico Mint are the most readily available, followed by the Lima Mint in Peru, Potosi Mint in Bolivia, with the Madrid Mint unique in private hands. Only one Holey Dollar has ties to the Guatemala Mint, and it is held in Chateau Ramezay, a museum in Montreal, Canada.

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Madrid Mint Holey Dollar, unique in private hands

This is the finest of six Continental Holey Dollars (two Seville Mint and four Madrid Mint) and the only example held in private hands. Noted in 1988 as 'the most desirable' of all Holey Dollars.

The Spanish Mints of Madrid and Seville produced silver dollars of a different design to those minted in the colonies and are referred to as Continental dollars. They were a status of Royalty, the Church and wealthy landowners and were as a consequence hoarded. Holey Dollars converted from Continental dollars are by default, exceedingly scarce.

Date of the silver dollar: 1802

Reigning monarch: Charles IV (1788 - 1808)

Design of the silver dollar: continental bust type

Portrait: Charles IV

Legend: Carolus (Charles) IIII

Mint mark: 'M' underneath a crown on the reverse

Quality of the silver dollar : Good Extremely Fine

Quality counter stamps: Good Extremely Fine

Exhibited: Macquarie Bank 2013, Royal Australian Mint 2019

Value $650,000+


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The finest Mexico Mint Holey Dollar, unique for quality

Miraculous preservation, unique for quality, and the finest Mexico Mint Holey Dollar. And the absolute finest of the three hundred Holey Dollars that are held in private collections and institutions, worldwide. 

This Holey Dollar is without peer. A Holey Dollar created from a Spanish Silver Dollar that shows no signs of circulation. It begs the question ... as the original silver dollar was minted in Mexico in 1805, how did it avoid usage in the seven years before it arrived in the colony of New South Wales? And how did it avoid usage after it was converted into a Holey Dollar? 

Date of the silver dollar: 1805

Reigning monarch: Charles IV (1788 - 1808)

Design of the silver dollar: colonial bust type

Portrait: Charles IV

Legend: Carolus (Charles) IIII

Mint mark: 'M' with a small circle above it in the legend on the reverse

Quality of silver dollar : Uncirculated

Quality counter stamps: Uncirculated

Value $600,000+


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The finest Potosi Mint Holey Dollar

Created from a Spanish Silver Dollar of the 'bust' type depicting the portrait and legend of Charles IV, this coin is the finest of sixteen Holey Dollars with ties to the Potosi Mint in Bolivia.

Great force had to be exerted on the Spanish Silver Dollar to punch out the central hole. As a consequence, many Holey Dollars are found slightly dished and distorted. With this Holey Dollar, the silver dollar flan is flat and has not been distorted by the cutting process. And the coin does not exhibit any metal fatigue. This is simply a fabulous Holey Dollar, the even shape allowing the design details to be displayed to the max.

Date of the silver dollar: 1807

Reigning monarch: Charles IV (1788 - 1808)

Design of the silver dollar: colonial bust type

Portrait: Charles IV

Legend: Carolus (Charles) IV

Mint mark: PTS monogram in the legend on the reverse said to be the inspiration of the '$' sign

Quality of the silver dollar : Extremely Fine

Quality counter stamps: Extremely Fine

Exhibited: Macquarie Bank 2013, Royal Australian Mint 2019

Value $500,000+


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The finest Lima Mint Holey Dollar

Created from a Spanish Silver Dollar of the 'bust' type depicting the portrait and legend of Charles IV, this coin is the finest of twenty two Holey Dollars with ties to the Lima Mint in Peru.

At Good Extremely Fine, this coin is in the top four of the three hundred Holey Dollars held in private collections and institutions, worldwide. We also note the counter stamps on the obverse, applied by William Henshall around the edge of the hole, are in the same vista as the date 1808. This is the optimum position of the counter stamps and was rarely ever achieved by mint master, William Henshall.

Date of the silver dollar: 1808

Reigning monarch: Charles IV (1788 - 1808)

Design of the silver dollar: colonial bust type

Portrait: Charles IV

Legend: Carolus (Charles) IV

Mint mark: LMAE monogram in the legend on the reverse

Quality of the silver dollar : Good Extremely Fine

Quality counter stamps: About Uncirculated

Exhibited: Macquarie Bank 2013, Royal Australian Mint 2019

Value $500,000+

Further reading .... how a penal colony established in 1788 was transformed into a commercial hub by 1813.

That Australia was settled in 1788, and the Holey Dollar and Dump not struck until 1813, raises the question about the medium of currency operating in the intervening years.

No consideration had been given to the monetary needs of the penal settlement of New South Wales. It was planned on the assumption that it would be self-supporting, with no apparent need for hard cash for either internal or external purposes.

Even if it had been theoretically planned for, it would have been physically impossible for the British Government to fund this new venture. Britain’s own currency was in a deplorable state and the Royal Mint’s priorities were clearly set at making improvements on the home front, not diverting hard cash off-shore.

Foreign coins arrived haphazardly in trade, and acquired local acceptability and brief legal recognition, but what was received quickly left the colony to pay for imports.

The essence of all business is a medium of exchange. Having very little hard cash, the inhabitants, from governor to free settlers and convicts, improvised by issuing hand-written promissory notes, in denominations as low as 3d, to settle their debts.

Commercial transactions were also facilitated through barter of goods and services. Philip Spalding, numismatist and author, presents an account of the style (and cunning) of barter in the colony circa 1800 in his literary works, ‘The World of the Holey Dollar’.

“One lover of the drama, not having rum or flour presented at the theatre door a neatly-dressed haunch of kangaroo, which was accepted. To the infinite disgust of the manager, it was discovered to be a haunch of a favourite greyhound, belonging to an officer, which the fellow had stolen, killed off and passed off as kangaroo meat at 9d per pound.”

Liquor was the prime commercial force and medium for barter in the colony and for almost forty years was part of the wages received by a considerable section of the population.

Governor Lachlan Macquarie’s communication to Viscount Castlereagh on the 30th April 1810 re-affirmed the financial plight of the colony. “In consequence of there being neither gold or silver coins of any denomination, nor any legal currency, as a substitute for specie in the colony, the people have been in some degree forced on the expedient of issuing and receiving notes of hand to supply the place of real money, and this petty banking has thrown open a door to frauds and impositions of a most grievous nature to the country at large.”

By 1812 the social fabric of Sydney as a community was emerging. It was no longer a redistribution point for convicts, with only the military as permanent residents.

Streets were being named. Macquarie, Phillip, Elizabeth, Castlereagh, Pitt and George Street. A post office was established and the common had been christened Hyde Park. Houses had to be aligned and numbered and heavy industry was being re-located out of the city centre to the suburbs.

Despite the social improvements, there was no bank and liquor remained the most commonly negotiated medium of currency exchange. 

Rum, which cost 7/6 a gallon was being sold for up to £8 and its use as a negotiating medium was utilized by all sections of the community, including government. And the highest levels of Government at that. Even Lachlan Macquarie used rum to buy a house. The cost? 200 gallons.

He furthermore gave the Government contract to construct the Sydney Hospital in 1811 to Messrs. Riley and Blaxcell and paid for it by granting a three-year monopoly in the spirit trade and the right to import 45,000 gallons of rum.

By 1812, the penal colony of New South Wales had shaken off the shackles of being a receptacle for convicts. It was no longer a ‘jail’. And was emerging as a structured society and a commercial hub.

The stage was set for Governor Lachlan Macquarie to introduce Australia’s first currency.


Governor Lachlan Macquarie etched his name into numismatic history forever when in 1812 he imported 40,000 Spanish Silver Dollars to alleviate a currency crisis in the infant colony of New South Wales.

The British Government had no capacity to supply Governor Lachlan Macquarie with metal blanks to create Australia’s first coinage so, he improvised and ordered 40,000 Spanish Silver Dollars - foreign coinage - to use as his substitute for blanks.

Concluding that the shipment of 40,000 Spanish Silver Dollars would not suffice, and to hinder their export, Macquarie decided to cut a hole in the centre of each dollar, thereby creating two coins out of one, a ring dollar and a disc. It was an extension of a practice of ‘cutting’ coins into segments, widely used throughout the British colonies of the Caribbean and several African nation’s including Sierra Leone.

Macquarie needed a skilled coiner to carry out his coining project. William Henshall, acquired his skills as an engraver in Birmingham, where the major portion of his apprenticeship consisted of mastering the art of die sinking and die stamping for the shoe buckle and engraved button trades. He was apprehended in 1805 for forgery (forging Bank of England Dollars) and sentenced to the penal colony of New South Wales for seven years.

Enlisted by Lachlan Macquarie as the colony’s first mint master, Henshall commenced the coining process by cutting out a disc from each silver dollar using a hand-lever punch.

He then proceeded to re-stamp both sides of the holed dollar around the inner circular edge with the value of five shillings, the date 1813 and the issuing authority of New South Wales. Other design elements in this re-stamping process included a fleur de lis, a twig of two leaves and a tiny ‘H’ for Henshall.

The Holey Dollars were officially known as ring, pierced or colonial dollars and although ‘holey’ was undoubtedly applied to them from the outset, the actual term ‘holey’ dollar did not appear in print until the 1820s.

We refer to the coins today as the 1813 New South Wales Five Shillings (or Holey Dollar).

The silver disc that fell out of the hole wasn’t wasted. Henshall restamped the disc with a crown, the issuing authority of New South Wales and the lesser value of 15 pence and it became known as the Dump. The term ‘dump’ was applied officially right from the beginning; a name that continues to this day.

In creating two coins out of one, Macquarie effectively doubled the money supply. And increased their total worth by 25 per cent.

Anyone counterfeiting ring dollars or dumps were liable to a seven year prison term; the same penalty applied for melting down. Jewellers were said to be particularly suspect. To prevent export, masters of ships were required to enter into a bond of £200 not to carry the coin away.

Of the 40,000 silver dollars imported by Macquarie, records indicate that 39,910 of each coin were delivered to the Deputy Commissary General’s Office by January 1814 with several despatched back to Britain as specimens, the balance assumed spoiled during production.

The New South Wales colonial administration began recalling Holey Dollars and Dumps and replacing them with sterling coinage from 1822.

The Holey Dollar and Dumps remained as currency within the colony until 1829. The colony had by then reverted to a standard based on sterling and a general order was issued by Governor Darling to withdraw and demonetise the dollars and dumps.

The recalled specie were eventually shipped off to the Royal Mint London, melted down and sold off to the Bank of England for £5044.

It is estimated that 300 Holey Dollars exist today of which a third are held in public institutions with the balance owned by private collectors.

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