In 1884, he found a dog with two heads and shot it with a shotgun, causing political turmoil. He ran unsuccessfully for a seat in the provincial assembly in 1886, losing to David Creighton; Cleland defeated Creighton to win the seat in 1890.
The event of a dog with two heads sparked controversy in 1884. In 1886, he made an unsuccessful bid for a seat in the provincial assembly, only to be defeated by David Creighton; however, Cleland's perseverance paid off when he defeated Creighton in 1890.