We examine the real-time dynamics of a system of one or more black holes interacting with long wavelength gravitational fields. We find that the (classical) renormalizability of the effective field theory that describes this system necessitates the introduction of a time dependent mass counterterm, and consequently the mass parameter must be promoted to a dynamical degree of freedom. To track the time evolution of this dynamical mass, we compute the expectation value of the energy-momentum tensor within the in-in formalism, and fix the time dependence by imposing energy-momentum conservation. Mass renormalization induces logarithmic ultraviolet divergences at quadratic order in the gravitational coupling, leading to a new time-dependent renormalization group (RG) equation for the mass parameter. We solve this RG equation and use the result to predict heretofore unknown high order logarithms in the energy distribution of gravitational radiation emitted from the system.