A slow bowler who could spin the ball harder and further than his contemporaries, Fleetwood-Smith was regarded as a rare talent, but his cricket suffered from a lack of self-discipline that also characterised his personal life.

Holding little regard for the other disciplines of the game, batting and fielding, he attracted a lot of attention with his rare style of bowling: left-arm wrist spin.

The third child of Fleetwood Smith and his wife Frances (née Swan), Fleetwood-Smith was born at Stawell in the Northern Grampians area of western Victoria.

[4] The family was well known in the district for their long involvement with the local newspaper, and for Fleetwood Smith's association with the organising committee of the Stawell Gift.

[4] In the early 1920s, he was a member of Xavier's powerful First XI, which included the future Test player Leo O'Brien, Joe Plant and Karl Schneider, who played first-class cricket while still at the school, but died of leukaemia at the age of 23.

[6] Fleetwood-Smith, and fellow Old Xaverians, Leo O'Brien, Stuart King and Joe Plant later represented Victoria v South Australia in a Sheffield Shield match at the MCG in February 1933.

[3] He became a regular in the club's First XI during his second season and in one match claimed 16 wickets for 82 runs (16/82) against Carlton, prompting his selection for the Victorian second team.

[11] In the winter of 1932, Fleetwood-Smith joined a private tour of the United States and Canada, organised by the former Test spin bowler Arthur Mailey.

[4] This rapid rise made Fleetwood-Smith a prospect for the Test team in 1932–33 when England toured and played the famous Bodyline series.

[3] However, in Ironmonger, Bill O'Reilly and Clarrie Grimmett, the Australian team possessed a strong spin bowling attack and Fleetwood-Smith needed to supplant one of the trio to gain selection.

Although he took 50 first-class wickets for the season (at 21.90 average, including 9/36 in an innings against Tasmania),[12] his bowling received rough treatment from Don Bradman in a match against New South Wales.

With Grimmett returned to favour, Fleetwood-Smith was unable to gain selection in the Test matches despite taking 106 first-class wickets (at a cost of 19.20 runs each) on the tour.

[12] Initially sceptical of his ability, Wisden thought that his bowling was "erratic" during the early part of the tour, but that he improved dramatically during the second half of the season.

Chosen to tour South Africa during the following summer, he made his belated Test debut in the opening match of the series at Durban.

[3] In his absence, Australia lost the opening two Tests of The Ashes series against England amid claims that the players were not responding well to their new captain, Don Bradman.

[24] Immediately after the match, Fleetwood-Smith, O'Reilly, Leo O'Brien and Stan McCabe were summoned to appear before four of Australia's leading cricket administrators, who read a prepared statement accusing the team of excessive drinking, inattention to fitness and disloyalty to the captain.

[28] Greg Growden, his biographer, records that Fleetwood-Smith had an unlikely friendship with Bradman (in that the two men were of opposite personalities), which later cooled after an unknown disagreement not associated with this incident.

Set a target of 392 runs to win, England reached 3/148 in their second innings by stumps on the fifth day, with their leading batsman Wally Hammond 39 not out and the match evenly poised.

A lovely ball lured Hammond forward, broke at the critical length, evaded the bat and bowled England's pivot and main hope ...

Wisden noted that he succeeded mainly against batsmen unfamiliar with his method and offered this ambivalent assessment: "He could not be written down as a failure but he certainly fell below expectations ..."[34] However, he played in every Test of the series for the only time in his career.

His seven wickets in the fourth Test at Leeds gave crucial support to O'Reilly, whose 10/122 was the key factor in the victory that enabled Australia to retain The Ashes.

Chuck you must remember was just silly, and totally around the bend ... As for his cricketing ability ... well, if I only had half of it, I never would have been worried about bowling against a team which had eleven Bradmans.Fleetwood-Smith was famed for his eccentric nature on the field.

He would sing, whistle, practice his golf swing, imitate birds such as magpies and kookaburras, pretend to catch imaginary butterflies, and shout encouragement for his favourite football team, Port Melbourne.

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.

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.

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.