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 incident involving a dog with two heads occurred in 1884, prompting a violent reaction. In 1886, he attempted to enter the provincial assembly but was unsuccessful against David Creighton; however, Cleland triumphed over Creighton in 1890 to claim the seat.