1907 - 1933
In 1938, the Times’ obituary of the longest-serving manager in Chelsea’s history remembered him as ‘one of the managers who started the fashion of paying huge transfer fees and was responsible for bringing many celebrated players to Stamford Bridge, including [Hughie] Gallacher and [Alex] Jackson
.’Club publications liked to depict the Hurlford, Ayrshire native as ‘inscrutable as the Sphinx’ – a man of few words but homespun wisdom aplenty. The secret to his longevity under an ambitious and combustible board may well have been gently fighting his corner while doing as he was told – he certainly enjoyed no real success in the dugout.
‘The directors were a big problem when it came to signing new players,’ noted Nils Middelboe, one of Calderhead’s most famous recruits. ‘They acted single-handedly, with the manager – the only person with any real knowledge of football – pushed into the background.’
As a centre-half, Calderhead’s playing career had taken in Queen of the South Wanderers, where he earned a solitary Scotland cap (which, he self-deprecatingly revealed, his wife used as an iron holder), and a Notts County side that won the FA Cup in 1894.
He had managed Lincoln City for seven years before joining the Pensioners (as Chelsea were nicknamed in our early decades), where reaching the club’s maiden FA Cup final in 1914/15 and achieving promotion twice (1912 and 1930) were the high water marks of his 26-year tenure as secretary-manager, 14 in the top-flight.
Indeed, when in 1928 he received a gold medal from the Football League it was in recognition of his 21 years’ service as club secretary. He had successfully put the squad back together after the First World War, and is the man chiefly responsible for the ‘moneybags Chelsea’ tag, his succession of glamorous signings regularly helping break national attendance records at the Bridge. However he must also accept much of the blame for Chelsea’s onetime reputation as ‘football’s great underachievers’ – perhaps that was the riddle of the Sphinx.
Calderhead retired in spring 1933, the same year music hall star Norman Long released a parody record, ‘The Day That Chelsea Went And Won The Cup.’ He passed away on 9 January 1938 at 42 Finlay Street, Fulham, aged 73.