Personal Life
On 28 February 1935, Fleetwood-Smith married Mary "Mollie" Elliott at St Mary's Catholic Church in East St Kilda. The wedding was a society event widely covered by the newspapers. Her family was well known in Melbourne for owning a prosperous soft-drink business; her father was an alderman of the city. Fleetwood-Smith had a reputation as a ladies' man who traded on his resemblance to the actor Clark Gable, and his infidelities after his marriage were not discreet. He joined the Elliotts' business as a sales representative, which brought him into daily contact with the pub trade and increased his alcohol consumption.
After the outbreak of World War II, Fleetwood-Smith enlisted in the Second Australian Imperial Force and was posted to the Army's Physical and Recreational Training School at Frankston where he served alongside Don Bradman as a Warrant Officer. He was involved in a collision with a nightcart when driving a borrowed army vehicle and the matter ended in court where he was ordered to pay costs. After less than a year's service, he was given a medical discharge in February 1941.
Fleetwood-Smith played the first post-war cricket season of 1945–46 for the Melbourne club and then retired with a tally of 252 wickets at 17.52 average in 74 district cricket matches, including four premiership teams. By this time, his marriage had broken down and his wife petitioned for divorce in June 1946, which was granted the following year. This alienated him from his family in Stawell as his ex-wife remained close to the Fleetwood-Smiths. He had lost his job with the Elliotts' company during the war. Fleetwood-Smith married Beatrix Collins (the sister of a teammate at Melbourne) at a registry office on 9 July 1948. He worked intermittently at menial jobs and his drinking increased; his second marriage also failed.
His arrest for vagrancy and theft in March 1969 was widely covered by the media. Appalled by his circumstance, a number of influential friends from his cricketing days, such as the former Australian Prime Minister Sir Robert Menzies, aided him by organising him legal assistance. The hearing was later adjourned, and he reconciled with his wife Bea after committing to remain sober. They lived together again for the last years of his life. However, the years of homelessness left him in poor health, and he died from cancer at St Vincent's Hospital in Fitzroy a fortnight before his 63rd birthday.
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