Early Career
Gardiner started his law career with Crooks, Roebuck and Parkinson. Gardiner turned down a partnership with the firm because Arthur W. Roebuck (a future attorney-general of Ontario) was too liberal, even though Roebuck took it as a personal slight. Gardiner left the practice in 1921 and joined Commercial Credit Company of Canada, as a legal associate. In 1923, Gardiner returned to law practice partnering with Harry Parkinson. The firm added H. Fred Parkinson and Donald H. Rowan to become the firm of Parkinson, Gardiner and Willis. Gardiner took criminal cases, litigation and continued to handle legal work with Commercial Credit. Gardiner attained the title of King's Counsel in 1938.
By 1945, Gardiner was considered one of the top half-dozen trial lawyers in the province and he commanded high fees. Gardiner was perceived as a stubborn and sometimes acid-tongued negotiator, and not a man to be crossed lightly as an opponent. Gardiner worked hard at research and marshalled detailed evidence with self-assurance.
Gardiner started investing in 1925, starting with $10,000, invested in industrial and mining stocks. He sold out in 1929 in time to avoid the crash, holding on only to shares of Noranda Mines. After the crash, he invested all of his capital in the Bank of Toronto, which became through merger today's Toronto-Dominion Bank. Gardiner also accepted stocks as payment for his legal fees and he amassed investments in a diverse number of companies. He was involved in real estate, metal stamping, manufacturing, forest products, aluminum products and car rentals. He partnered with Sam Steinberg in Drayton Motors, a large used car dealership. He also partnered with Steinberg in Sage Enterprises, managing hotels.
Gardiner became indulgent, chartering aircraft for weekends of fishing. He continued to gamble, losing $6,000 in one night in the late 1930s. Gardiner's drinking increased until 1940, when Audrey convinced him to give it up. He did not drink again until 1949, and when he started, he drank more moderately. In conjunction with drinking less, Gardiner also lessened his gambling and took up golf. He also developed an interest in growing red roses, for which he won horticultural prizes. He also took an interest in visual arts, assembling a collecion of landscape and portrait painting, and collected modern and antique silver artifacts.
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