When R.B. attended the Dalhousie Law School in Halifax, Nova Scotia, the dean of law was Richard Chapman Weldon.
Weldon had become the first full-time professor of law in post-confederation Canada when the Law Faculty was created at Dalhousie University in 1883. Shortly afterwards, in 1887, Weldon ventured into federal politics and became the Member of Parliament for the riding of Albert, New Brunswick, R.B.'s home riding. R.B. helped Weldon during the re-election campaign in 1891 while he was a student at the Law School.
ames Lougheed had established a law practice in Calgary, Northwest Territories, and was appointed as the Canadian Pacific Railway's solicitor in Calgary before the railway even got there. On December 10, 1889, Lougheed was appointed to the Senate of Canada. To continue his lucrative law firm Lougheed took on a partner. He went through several local lawyers without much success. He decided to look farther afield for a junior lawyer to join his law firm and so he asked for a recommendation from Richard Weldon, dean of the Dalhousie Law School. The recommendation he received was for R.B. Bennett.
R.B. moved to Calgary in January of 1897, just months after the Chatham council election. After settling into a room at the Alberta Hotel on Stephen Avenue, R.B. settled into his new career. The Lougheed and Bennett law office was located on the second floor of the Clarence Block, which was across the street and just fifty yards east of the Alberta Hotel.
R.B. dove into his new life with a work ethic and determination that can only come from maritime origins. The Lougheed and Bennett law firm represented some important clients - the Bank of Montreal, the Royal Bank, Bank of Nova Scotia, Bank of Commerce, Merchants Bank, Crown Trust, Union Trust, Crown Life, Great West Life, Ontario Loan and Debenture Company, Berbeck Investment Company, Massey Harris, R.G. Dun, and the Canadian Pacific Railway. Using the connections that he made and continuously learning in every way possible, he very carefully made decisions and investments. He made many lucrative real estate transactions as more and more people moved westward.
In 1888 the Dominion of Canada sold a ninety-four acre property on the southern edge of Calgary to the Calgary and District Agricultural Association and placed a caveat on the property that it was to be solely used for an agricultural exhibition. The association placed a mortgage on the property. The exhibition failed to attract enough interest to justify its existence and went out of business in 1892 leaving an unpaid mortgage.
When the Calgary exhibition was revived in 1901 the Inter-Western Pacific Exhibition Company found that the property had been sold by the trust company that held the mortgage to R.B. Bennett. R.B. agreed to sell the property for $7000. The exhibition could not afford the large amount so they convinced the City of Calgary to buy the property for them. The property is still home to the Calgary Stampede today.
Max Aitken arrived in Calgary in the spring of 1898.
On August 30, 1898, R.B. announced his candidacy for the upcoming Territorial Assembly election. Aitken helped R.B. with the campaign and R.B. won the seat. R.B. pushed for provincial status for Alberta and fought against railway monopoly and the discriminatory freight-rate structure all the while being the solicitor for the Canadian Pacific Railway.
R.B. resigned his Territorial Assembly seat to run for parliament in the 1900 Federal election. He lost. He was able to reclaim his Territorial Assembly seat in a 1901 by-election.
R.B. did not seek the leadership of the Alberta Conservative party when the convention was held in the summer of 1905 but he was the unanimous choice. The province of Alberta was officially created on September 1, 1905 and the first general election was held on November 9 of the same year. Under R.B.'s leadership the Conservative party only won two out of the 25 seats in the Legislative Assembly of Alberta. R.B. did not win his. He promptly resigned from the leadership of the party and returned to his work in the Lougheed and Bennett firm.