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Reconsidering the humoristic process as part of the categories of transitional phenomena, this paper proposes to follow the theoretical clinical paths left open by D.W. Winnicott. Humour is presented as the rebellious destiny of primary illusion, which make it a very sharp tool for fighting against the infringement of the superego and exterior reality. But if it invests the transitional area as a base for strategic retreat, it is also an original creation susceptible to opening up the functions of the psyche. Are these mutative properties applicable to the work of a psychotherapist? This is the primary question in the clinical discussion regarding Samir’s defensive reorganization.