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Macdonald's parents decided he should become a lawyer after leaving school. As Donald Creighton (who penned a two-volume biography of Macdonald in the 1950s) wrote, "law was a broad, well-trodden path to comfort, influence, even to power". It was also "the obvious choice for a boy who seemed as attracted to study as he was uninterested in trade." Macdonald needed to start earning money immediately to support his family because his father's businesses were failing. "I had no boyhood," he complained many years later. "From the age of 15, I began to earn my own living."
Macdonald travelled by steamboat to Toronto (known until 1834 as York), where he passed an examination set by The Law Society of Upper Canada. British North America had no law schools in 1830; students were examined when beginning and ending their tutelage. Between the two examinations, they were apprenticed, or articled to established lawyers. Macdonald began his apprenticeship with George Mackenzie, a prominent young lawyer who was a well-regarded member of Kingston's rising Scottish community. Mackenzie practised corporate law, a lucrative speciality that Macdonald himself would later pursue. Macdonald was a promising student, and in the summer of 1833, managed the Mackenzie office when his employer went on a business trip to Montreal and Quebec in Lower Canada (today the southern portion of the province of Quebec). Later that year, Macdonald was sent to manage the law office of a Mackenzie cousin who had fallen ill.
In August 1834, George Mackenzie died of cholera. With his supervising lawyer dead, Macdonald remained at the cousin's law office in Hallowell (today Picton, Ontario). In 1835, Macdonald returned to Kingston, and even though not yet of age nor qualified, began his practice as a lawyer, hoping to gain his former employer's clients. Macdonald's parents and sisters also returned to Kingston.
Soon after Macdonald was called to the Bar in February 1836, he arranged to take in two students; both became, like Macdonald, Fathers of Confederation. Oliver Mowat became premier of Ontario, and Alexander Campbell a federal cabinet minister and Lieutenant Governor of Ontario. One early client was Eliza Grimason, an Irish immigrant then aged sixteen, who sought advice concerning a shop she and her husband wanted to buy. Grimason would become one of Macdonald's richest and most loyal supporters, and may have also become his lover. Macdonald joined many local organisations, seeking to become well known in the town. He also sought out high-profile cases, representing accused child rapist William Brass. Brass was hanged for his crime, but Macdonald attracted positive press comments for the quality of his defence. According to one of his biographers, Richard Gwyn:
All male Upper Canadians between 18 and 60 years of age were members of the Sedentary Militia, which was called into active duty during the Rebellions of 1837. Macdonald served as a private in the 3rd Frontenac Militia, patrolling the area around Kingston, but the town saw no real action and Macdonald was not called upon to fire on the enemy.
Sir Joseph Pope, Macdonald's private secretary, recalled Macdonald's account of his experience during the 1837 Upper Canada Rebellion:
Although most of the trials resulting from the Upper Canada Rebellion took place in Toronto, Macdonald represented one of the defendants in the one trial to take place in Kingston. All the Kingston defendants were acquitted, and a local paper described Macdonald as "one of the youngest barristers in the Province [who] is rapidly rising in his profession".
In late 1838, Macdonald agreed to advise one of a group of American raiders who had crossed the border to liberate Canada from what they saw as the yoke of British colonial oppression. The invaders had been captured after the Battle of the Windmill near Prescott, Upper Canada. Public opinion was inflamed against the prisoners, as they were accused of mutilating the body of a dead Canadian lieutenant. Macdonald could not represent the prisoners, as they were tried by court-martial and civilian counsel had no standing. At the request of Kingston relatives of Daniel George, paymaster of the ill-fated invasion, Macdonald agreed to advise George, who, like the other prisoners, had to conduct his own defence. George was convicted and hanged. According to Macdonald biographer Donald Swainson, "By 1838, Macdonald's position was secure. He was a public figure, a popular young man, and a senior lawyer."
Macdonald continued to expand his practice while being appointed director of many companies, mainly in Kingston. Macdonald became both a director of and a lawyer for the new Commercial Bank of the Midland District. Throughout the 1840s, Macdonald invested heavily in real estate, including commercial properties in downtown Toronto. Meanwhile, he was suffering from some illness, and in 1841, his father died. Sick and grieving, he decided to take a lengthy holiday in Britain in early 1842. He left for the journey well supplied with money, as he spent the last three days before his departure gambling at the card game loo and winning substantially. Sometime during his two months in Britain, he met his first cousin, Isabella Clark. As Macdonald did not mention her in his letters home, the circumstances of their meeting are not known. In late 1842, Isabella journeyed to Kingston to visit with a sister. The visit stretched for nearly a year before John and Isabella Macdonald married on September 1, 1843.