Measurement can be harnessed to probabilistically generate entanglement in the absence of local interactions, for example between spatially separated quantum objects. Continuous weak measurement allows us to observe the dynamics associated with this process. In particular, we perform joint dispersive readout of two superconducting transmon qubits in two remote cavities. We track the evolution of a joint quantum state under the influence of measurement, both as an ensemble and as a set of individual quantum trajectories. Analyzing the statistics of such quantum trajectories can shed new light on the underlying entangling mechanism.