The study presents a sustainable, metal-free tanning system based on 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and N-methylmorpholine (NMM), which stabilizes collagen through a zero-length crosslinking mechanism. Reactive triazine intermediates, generated in situ, selectively activate collagen carboxyl groups, forming active esters that subsequently react with amine functionalities to form amide bonds. Unlike conventional tanning systems, no metals or toxic chemicals are incorporated into the tanned leather. Optimization of reagent concentration, temperature, and dosing strategy revealed that the gradual formation of reactive intermediates is essential to balance reaction kinetics and diffusion throughout collagen. Under pickle-free conditions, hydrothermal stability was achieved with only 2.5–3.4 wt% CDMT/NMM, yielding shrinkage temperatures of 81–85 °C that surpass most reported chrome-free tanning systems. The resulting leather displayed a bright white appearance, excellent dyeability, and outstanding physical-mechanical performance, including superior tear resistance and competitive tensile strength. These properties are consistent with the formation of a homogeneous collagen network reinforced by direct covalent amide crosslinks while maintaining fiber flexibility. Furthermore, avoiding pickling significantly reduces chemical consumption and improves wastewater biodegradability, enhancing the environmental sustainability of the process. Overall, CDMT/NMM emerges as a scalable, environmentally friendly tanning technology that combines mechanistically controlled collagen crosslinking with excellent leather performance.