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.
The next Alberta provincial election was held on March 22, 1909. Prior to the election, the Conservatives in Calgary held a nominating convention. R.B. was absent from the city at the time. It was actually a friend, George Robinson, that placed R.B.'s name in nomination, without his consent. Again, R.B. was the unanimous choice. Rather than embarrassing his friend and the Conservative party, R.B. chose to accept the nomination. The Conservative party, again, only won two seats. This time there were a total of 41 seats in the legislature and R.B. won his seat.
In early 1910 a political problem surfaced for the majority government Liberal's in Alberta. The Alberta and Great Waterways Railway was the center of a controversy that nearly brought down the government. The debate was in full swing, both in the legislature and outside it, before R.B. finally rose from his seat to express his position. The Edmonton Journal reported:
"Yesterday's sittings of the Legislature were the most sensational in the history of the young province of Alberta. Never in its four and a half year life has such interest attended a debate on the political questions of the day. Never before had the members of the legislature and those who crowded into every nook of the building witnessed such a display of forensic eloquence as was given in the afternoon and evening session.
The long looked for speech of R.B. Bennett on the Great Waterways agreement marked a new era in the local legislature. For in the splendor of the diction and the physical endurance of the orator it established a high water mark for Parliamentary debate in Alberta. Exclusive of the two-hour adjournment he addressed the house for more than five hours in a flow of eloquence that was fully sustained from start to finish.... He held his listeners spellbound from start to finish."
The fiasco boiled down to a dispute between the Alberta government and the Royal Bank over who should possess the remaining $6 million that was raised from British bondholders for the railway. The government demanded the money from the bank and, on R.B.'s advice, the bank refused. The government sued and won in the Alberta Supreme Court. The bank, again on R.B's advice, then sought leave to appeal to the Privy Council in England, the highest court of appeal for Canada at the time, and leave was granted. R.B. himself argued the case before the Privy Council on December 10, 1912, and the decision was handed down on January 31, 1913. R.B. won. Simply arguing a case before the Privy Council would be the high point of any legal career but to win the case made it even more rewarding.
R.B. grew frustrated with the Alberta provincial political scene and decided to run for a seat in the September 21, 1911 federal election. Although he was clearly the underdog in the Calgary riding at the beginning of the election campaign, he rose to the challenge and won a resounding victory on Election Day.