Waste rubbers have caused a severe environmental pollution now. Their reutilization is an urgent eco-economic demand for the sustainable society by converting the wastes into feedstock for the chemical industry. In the present work, the metathetic degradation of waste rubbers (waste natural rubber gloves as model) was comprehensively investigated with different chain transfer agents (CTAs). The waste natural rubber gloves could be degraded with three CTAs with different polarities (styrene, methyl acrylate (MA) and acrylic acid (AA)), catalyzing with the HG2 catalyst in chloroform. Four kinds of main reactions were proposed in the olefin cross-metathesis (OCM) degradation, based on the product analysis. It was also found that the degradation was favored by a consistent low concentration of the CTA, inhibiting the by-reactions and subsequently improving the degradation yield. Therefore, an easy and effective strategy for the high-performance OCM degradation of waste rubbers was proposed by dropping the CTA.