A mechanism is proposed for the degradation of natural rubber by the cold mastication process. The rubber hydrocarbon is considered to be ruptured into free radicals by the deformation of the rubber. These recombine, or react with oxygen or other suitable reactant, and thereafter do not necessarily recombine. Experimental evidence supporting this mechanism is reported, mainly the masticating or rubber in an atmosphere of nitrogen after incorporation of substances likely to interact with the radical ends of the ruptured chains. Forty‐seven substances functioning in this way are listed. A more detailed study has been carried out with one of these, benzoquinone, varying separately concentration, time of mastication, temperature, and mean chain length of rubber. A similar mechanism is shown to apply to the synthetic rubbers tested. The probable chemical reactions occuring and the correlation of cold mastication with other freeradical systems are discussed. The role of oxygen in cold mastication is considered in detail. The possible significance and practical application of the work is suggested.