We study the Landau-Zener dynamics of a tunneling spin coupled to a torsional resonator. For strong spin-phonon coupling, when the oscillator frequency is large compared to the tunnel splitting, the system exhibits multiple Landau-Zener transitions. Entanglement of spin and mechanical angular momentum results in abrupt changes of oscillator dynamics which coincide in time with spin transitions. We show that a large number of spins on a single oscillator coupled only through the in-phase phonon field behaves as a single large spin, greatly enhancing the spin-phonon coupling. We compare purely quantum and semiclassical dynamics of the system and discuss their experimental realizations. An experiment is proposed in which the field sweep is used to read out the exact quantum state of the mechanical resonator.