Well, an internet search reveals that the Cherokee was rated for towing 2000-5000lbs, based on eqpt. The Globetrotter weighs 3300 dry, prob 4000 ready for the road. If the Jeep is in good shape, with good brakes and well-maintained suspension, and a healthy transmission with a cooler....then, probably. You could make a case for a lightweight, weight distributing hitch like an Anderson to increase stability, since the Jeep only weighs about 3000#. The smaller and lighter the trailer, the better.