As a child, MacDonald met many painters through family connections and, in the mid-1890s, studied at the National Gallery of Victoria's school.
On 9 September 1914, with the outbreak of the First World War, MacDonald enlisted in the 5th Battalion, Australian Imperial Force.
With the rank of private, he served at Gallipoli where, on 26 April 1915, he was wounded in the abdomen and was classified unfit for active service.
[2] Returning to Australia, MacDonald took up art study, publishing works on Frederick McCubbin, Penleigh Boyd, David Davies and George Lambert.
His relationship with the Trustees became strained, particularly the chairman, Sir Keith Murdoch, who resented his ferocious attacks on contemporary art.
[3] In 1943, he was first witness on behalf of those who brought an action against the award of the Archibald Prize to William Dobell for his portrait of Joshua Smith.