We present results from a 42 ks Chandra/ACIS-S observation of the transitional FR I/FR II radio galaxy 3C 288 at z = 0.246. We detect ~3 keV gas extending to a radius of ~0.5 Mpc with a 0.5-2.0 keV luminosity of 6.6 × 1043 erg s-1, implying that 3C 288 lies at the center of a poor cluster. We find multiple surface brightness discontinuities in the gas indicative of either a shock driven by the inflation of the radio lobes or a recent merger event. The temperature across the discontinuities is roughly constant with no signature of a cool core, thus disfavoring either the merger cold front or sloshing scenarios. We argue therefore that the discontinuities are shocks due to the supersonic inflation of the radio lobes. If they are shocks, the energy of the outburst is ~1060 erg, or roughly 30% of the thermal energy of the gas within the radius of the shock, assuming that the shocks are part of a front produced by a single outburst. The cooling time of the gas is ~108 yr, so that the energy deposited by the nuclear outburst could have reheated and efficiently disrupted a cool core.