Innkeeper's son to surgeon to highwayman to richest Australian
Surprisingly, in light of what will have read if you have read the previous pages of this section of our website, one of the first to profit from Macquarie's kindness was a man who was both wealthy and not a convict. Although his ongoing state of freedom was only due to luck and good connections. He was an extremely enterprising surgeon with distant noble connections who had been sent out to the colony after managing to escape being hanged, imprisoned, or transported when he was caught working on the side as a highwayman. As far as the other wealthy people were concerned, he was as good, or rather bad, as any convict, and was not accepted into the dizzy heights of their colonial bunyip society.
One of this bloke's jobs was to treat Macquarie's syphilitic ulcers, some of which were in the genital region, with various treatments, including cauterisation with hot wires. Macquarie, possibly because he trusted D'Arcy Wentworth, for that was the surgeon's name, or because he wanted to make sure D'Arcy's hands didn't shake at the risk of ever becoming poor, decided to help him along a bit.
D'Arcy the highwayman became the colony's Chief Surgeon, a justice-of-the-peace, a magistrate, a member of the Governor's Court (Macquarie's advisory body), commissioner of police (incredibly), treasurer of the Police Fund (monies collected by taxes and tolls and for use not just on the police, but also colonial infrastructure and various other government expenditures, after, presumably, D'Arcy took his share), and turnpike commissioner (the bloke responsible for collecting highway tolls). You can imagine how these appointments were regarded by people who believed D'Arcy's body should have stinkingly rotted on the end of a noosed rope. And not a silken one, either.