The phrase Awkward Squad is used usually to refer to any grouping of individuals, normally within an existing organisation or structure, who are incompetent or wittingly or otherwise associate together to resist or obstruct change and are possibly stubborn in doing so.
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It is commonly accepted that shortly before his death in 1796 Robert Burns uttered the words "Don't let the awkward squad fire over me".[1][1] So at least by the end of 18th century the phrase was already in use in military slang for a group of recruits who seemed incapable of understanding discipline or not yet sufficiently trained or disciplined to properly carry out their duties [2] [3][2].
John Clare (English peasant poet) wrote with his own spelling and no punctuation: he complained c.1820-1830 to his editors that people could understand him, and that he wouldn't use "that awkward squad of colon, semi-colon, comma, and full stop" (source - display in Clare's cottage, Helpston.)
In Villette (pub. 1853) Charlotte Bronte writes of M. Paul Emanuel: "Irritable he was; one heard that, as he apostrophized with vehemence the awkward squad under his orders."
In Chapter 16 of Our Mutual Friend (1864-65), Charles Dickens describes the character Sloppy as "[A] Full-Private Number One in the Awkward Squad of the rank and file of life."
Norman Cameron ends one of his poems - Forgive me, sire - with the words 'awkward squad' , which plays with the above definition. This would have been written at least about 50 years before the current use.
The tag of the 'Awkward Squad' is applied to a current group of left-wing trade unionists in the United Kingdom, marked out by their opposition to the Labour Party's economic policies. The group includes Bob Crow, Mark Serwotka, and Tony Woodley.