The excessive use of plastics has led to severe global problems involving environmental, energy, and health issues and demands for sustainable and recyclable alternatives. Toward circular plastics, the development of efficient chemical recycling methods without loss of properties or allowing reprocessing into new materials offer tremendous opportunities. Here, we report an intrinsically recyclable and reconfigurable poly(disulfide) polymer using a natural small molecule, thioctic acid (TA), as the feedstock. Taking advantage of its dynamic covalent ring-opening polymerization, this material enables a dual closed-loop chemical recycling network among TA monomers and two kinds of polymer products, including self-healing elastomers and mechanically robust ionic films. Mild and complete depolymerization into monomers in diluted alkaline aqueous solution is achieved with yields of recovered monomers up to 86%. The polymer materials can be repeatedly recycled and reused with reconfigurable polymer composition and tunable mechanical properties offering prospects for sustainable functional plastics.