Hugh John Montgomery was born in Bedeque, Prince Edward Island on July 31, 1878.

He grew up on the island and attended Charlottetown Business College [2] He moved west in 1898 after graduating and settled in Wetaskiwin when it was still in the Northwest Territories.

[2] Montgomery first ran for a seat to the Alberta Legislature in a by-election on November 17, 1914, in the electoral district of Wetaskiwin.

Montgomery was elected by a wide margin over Conservative candidate Finlay Watson, who thus lost his deposit.

[8] Montgomery was defeated again in the 1935 general election, this time by John Wingblade of the Social Credit League.