James Roberts was a New Zealand trade unionist, politician and was president of the Labour Party from 1937 to 1950. He was called 'Big Jim' and 'the uncrowned King of New Zealand' in recognition of the considerable influence he wielded during the period of the First Labour Government over policy creation and implementation.

The 1944 Wellington City mayoral election was part of the New Zealand local elections held that same year. In 1944, election were held for the Mayor of Wellington plus other local government positions including fifteen city councillors. The polling was conducted using the standard first-past-the-post electoral method.