Meaning
To go through hell / To have a rough time
Example
Antes de ficar rico, ele comeu o pão que o diabo amassou.
Before becoming rich, he went through hell.
Origin
The force of comer o pão que o diabo amassou lies in its imagery. In the Christian tradition bread is the supreme symbol of life and blessing; bread kneaded by the devil is therefore its cursed opposite — a loaf made of malice and hardship. To eat it is to be fed nothing but suffering.
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More idioms
Acertar na moscaTo guess correctly / To hit the nail on the headAmigo da onçaA fake/false friendAndar na linhaTo toe the line / To behave properlyArmar um barracoTo cause a public sceneRodar a baianaTo cause a public scene / To go ballisticArrumar sarna pra se coçarTo ask for troubleArrastar as asasTo hit on someone / To flirtAbrir o jogoTo come clean / To open upArregaçar as mangasTo roll up one's sleeves / To get to workAgarrar com unhas e dentesTo hold on for dear life / To seize an opportunity