How do ion–dipole bonds manage to break apart an ionic lattice?

Question

I was reading this answer and its reasoning behind the dissolution of NaCl seems to lie in entropic favorability. However, as it states, many, if not most, dissolution reactions are favored by enthalpy (i.e. exothermic). Reasoning with energy alone, without entropy, it seems that ion–dipole forces are greater than the Coulombic forces between the ions themselves. However, how can this be? Aren’t ionic bonds second only to covalent bonds? How can water molecules form ion–dipole bonds with ions that are stronger than the ionic bonds within the lattice?