We obtain the representation of the backward shift operator on Chebyshev polynomials involving a principal value (PV) integral. Twice the backward shift on the space of square-summable sequences l2 displays chaotic dynamics, thus we provide an explicit form of a chaotic operator on L2 (−1, 1, (1−x2)–1/2) using Cauchy’s PV integral. We explicitly calculate the periodic points of the operator and provide examples of unbounded trajectories, as well as chaotic ones. Histograms and recurrence plots of shifts of random Chebyshev expansions display interesting behaviour over fractal measures.