In the framework of Lindblad theory for open quantum systems, we calculate the entropy of a damped quantum harmonic oscillator which is initially in a quasi-free state. The maximally predictable states are identified as those states producing the minimum entropy increase after a long enough time. In general, the states with a squeezing parameter depending on the environments diffusion coefficients and friction constant are singled out, but if the friction constant is much smaller than the oscillators frequency, coherent states (or thermalized coherent states) are obtained as the preferred classical states.