We investigate the nonequilibrium dynamics of a Josephson-coupled Jaynes-Cummings dimer in the presence of Kerr nonlinearity, which can be realized in the cavity and circuit quantum electrodynamics systems. The semiclassical dynamics is analyzed systematically to chart out a variety of photonic Josephson oscillations and their regime of stability. Different types of transitions between the dynamical states lead to the self-trapping phenomenon, which results in photon population imbalance between the two cavities. We also study the dynamics quantum mechanically to identify characteristic features of different steady states and to explore fascinating quantum effects, such as spin dephasing, phase fluctuation, and revival phenomena of the photon field, as well as the entanglement of spin qubits. For a particular "self-trapped" state, the mutual information between the atomic qubits exhibits a direct correlation with the photon population imbalance, which is promising for generating photon mediated entanglement between two non interacting qubits in a controlled manner. Under a sudden quench from stable to unstable regime, the photon distribution exhibits phase space mixing with a rapid loss of coherence, resembling a thermal state. Finally, we discuss the relevance of the new results in experiments, which can have applications in quantum information processing and quantum technologies.