The differing perspectives and actions of US government, business and labour towards the Guatemalan government and Guatemalan trade unionists themselves in the half-decade or so following the overthrow of the Arbenz administration in 1954 are the focus of this study. Few areas were more important to the US project for Guatemala following the Castillo Armas invasion than helping the Guatemalans to create a ‘free’ and ‘democratic’ labour movement – and few areas would prove more frustrating. Part of the problem was the intransigent stance of Guatemalan elites. An additional challenge was strong opposition from the major US-based companies operating in Guatemala, most notably the United Fruit Company and its affiliates. This work contests interpretations that regard US policy towards countries like Guatemala at the time as simply beholden to business interests or as seeking domination. Rather, as Washington's interest in the transition diminished, officials in the US embassy and representatives of US labour in Guatemala were left isolated, unable to fulfil their vision for a democratic labour movement in the teeth of such opposition.