Owing to the inherently probabilistic nature of quantum mechanics, each experimental realization of a dynamical quantum system may yield a different measurement outcome, especially when the system is coupled to an environment that may cause spontaneous emission. Although it is, in principle, possible that some quantum trajectories lead to exotic highly-entangled quantum states, the probability of observing these trajectories is usually extremely low. In the talk, I will show how to maximize the probability of generating highly entangled states, including maximally entangled cat states, in an ensemble of atoms experiencing superradiant decay into a cavity mode. To this end, I will analyze an effective non-Hermitian Hamiltonian which governs the dynamics between the quantum jumps associated with photon emission.