The template-enhanced ring-opening metathesis polymerization (ROMP) of a norbornene-based thymine monomer was examined. The template, based on diaminopyridine functionalized norbornenes that are designed to recognize thymine substrates with high fidelity, was synthesized via ROMP. The resulting template was used to harness the polymerization of the thymine monomer producing a bis-poly(norbornene) complex. Using 1 H NMR spectroscopy, we determined that the polymerization conditions do not disrupt the hydrogen bonding. In addition, the template enhances the rate of the polymerization by inducing an increase in local monomer concentration. To examine whether the polymerization is controlled, we synthesized a solid-supported diaminopyridine template. After the polymerization off this solid-supported template, we extracted the daughter polymer from the support. Detailed analysis of the daughter template proved that the templated polymerization was controlled and that the supported template produces a well-defined daughter polymer.