Ives became a lawyer in Montreal shortly after graduating, being called to the bar in 1900, and worked in the city for two years before moving back to Alberta.

[2][1] Ives moved to the town of Lethbridge in 1901 and joined a legal firm partnering with established lawyer Charles Conybeare.

He again finished second, this time in a three way race ahead of incumbent Labor MLA Donald McNabb but was defeated by Liberal candidate William Ashbury Buchanan.

[1] Ives judgements were known to be short and to the point, and rarely reserved cases, and was known, and sometimes criticized for the assistance he would provide young and inexperienced lawyers in the court room.

After the jury verdict came down, Ives threw out the jury decision in favour of the plaintiffs and dismissed the case; the Supreme Court of Canada eventually overturned Ives' decision The trial scandalized the United Farmers government and helped lead to its defeat in the 1935 Alberta general election.

Ives would find both defendants guilty on charges of conspiracy, and sentenced them to four months hard labour and fined $275,000.