Recruited from
Northcote, Regan struggled in his first few seasons and was tried in a variety of positions before he established himself at full-back. Taking on and matching full-forwards like
South Melbourne's
Bob Pratt (whom Regan regarded as his most difficult opponent),
Carlton's
Harry Vallence,
Richmond's
Jack Titus and
St Kilda's
Bill Mohr, Regan earned his title as the "Prince of Full-backs". He was a magnificent mark and a superb kick. Archival footage shows him using the now defunct drop kick for his kick-ins. In slow motion they demonstrate his perfect balance and timing. Regan was among the best players in the Magpies'
1935 and
1936 premiership victories, both against
South Melbourne. In May
1938, during a match against
Carlton, Regan fell heavily and suffered a double dislocation of an elbow. He spent a week at
St Vincent's Hospital, and ended up missing nine matches. He recovered in time to play a part in Collingwood's finals campaign, but again for the second successive year was on the losing end as Carlton emerged victorious with the
1938 pennant. In January 1942 Regan announced his retirement from football to join the
Salesian community at
Sunbury as a lay brother. In February 1943, with Australia now involved heavily in the Second World War, Regan enlisted with the
Royal Australian Air Force (RAAF) and served as a
leading aircraftman. He returned in
1943 to captain Collingwood. In April 1946, shortly after being discharged from military service, Regan returned to Collingwood and trained so well that he was selected for their Round 1 match of the
1946 season against
Hawthorn. In March 1947, it was announced that Regan had been appointed coach of
Kalgoorlie City Football Club in
Goldfields Football League.
Essendon champion
Dick Reynolds considered Regan the best full-back he ever saw. In an article for Melbourne newspaper
The Argus Reynolds recounted watching Regan play state football against the likes of
Ken Farmer from
South Australia and
George Doig from
Western Australia and said:
[H]e made them earn every goal they kicked against him. It was great to see the way in which he shadowed them or marked or punched the ball away, and then, with great dash and a beautiful kick, sent the ball in the right position for an attack. His quick thinking and unruffled style at critical moments made him a star full-back. During his playing career, Regan had worked as a clerk for the Commonwealth Social Service in Melbourne. After returning to Melbourne from Kalgoorlie he continued to serve at Collingwood for many years, and was club secretary from 1969 to 1977. == Posthumous honours ==