We investigate a wide range of possible evolutionary histories for the recently discovered Bootes dwarf spheroidal galaxy, a Milky Way satellite. By means of N-body simulations, we follow the evolution of possible progenitor galaxies of Bootes for a variety of orbits in the gravitational potential of the Milky Way. The progenitors considered cover the range from dark matter-free star clusters to massive, dark matter-dominated outcomes of cosmological simulations. For each type of progenitor and orbit, we compare the observable properties of the remnant after 10 Gyr with those of Bootes observed today. Our study suggests that the progenitor of Bootes must have been, and remains now, dark matter-dominated. In general, our models are unable to reproduce the observed high velocity dispersion in Bootes without dark matter. Our models do not support time-dependent tidal effects as a mechanism able to inflate significantly the internal velocity dispersion. As none of our initially spherical models is able to reproduce the elongation of Bootes, our results suggest that the progenitor of Bootes may have had some intrinsic flattening. Although the focus of this paper is the Bootes dwarf spheroidal, these models may be of general relevance to understanding the structure, stability and dark matter content of all dwarf spheroidal galaxies.