The hypothesis doesn't make much sense. The resistance of an object to being ripped apart is given by its elasticity, not by how much is massive.
Anyway, to the central question there is no answer yet. This is the so called information loss paradox, one of the greatest unsolved problem in theoretical physics.
In general relativity the object falls in a finite amount of proper time and hit a singularity (assuming the most simple black hole, Schwarzschild). Due to Hawking radiation the hole evaporates completely and information is lost because a pure state has evolved into a mixed state.
One of the most promising resolutions to the paradox is given by string theory: the fuzzball proposal. Basically the hole is a sort of very degenerate stringy star (there is an over-over simplification here) free of horizon and singularites that radiates more like an usual piece of burning coal, so the information is not lost. The crucial point is that (in the usual simplified picture of pair particles produced near the horizon) the place in which the particle are produced is NOT vacuum, so the there is not information paradox in the first place.