A gambling demon is an external agent that can terminate a time-dependent driving protocol when a certain observable of the system exceeds a prescribed threshold. The gambling demon is examined in detail both theoretically and experimentally in a Brownian particle system under a compressing potential trap. Insight for choosing an appropriate work threshold for stopping is discussed. The energetics and the distributions of the stopping positions and stopping times are measured in simulations to gain further understanding of the process. Furthermore, the nonstationary and far-from-equilibrium stochastic process in the action of the gambling demon allows us to examine in detail some fundamental issues in stochastic thermodynamics, such as irreversibility and stopping-time fluctuation relation. Paradoxical violation of the stopping-time fluctuation relation can be reconciled in terms of the entropy production associated with fast hidden internal degrees of freedom. All the simulation or theoretical results are confirmed experimentally.