Chelating extraction of heavy metals from contaminated soils is seen as a remediation technique. This work addresses important consideration in the application of chelating agents for soil remediation, namely the complexing power, selectivity, and recoverability of the chelators with respect to heavy metal contaminants. To address these issues, an assessment technique was developed to evaluate the chelators based on complexation equilibria of the chelators toward the target metals including Pb, Cu, Cd, Zn, Ni, and Hg. Predictions in terms of complexing power and selectivity were made using this technique and were compared to experimental extraction results using several chelators including L-5-glutamyl-L-cysteinylglycine (GCG), ethylenediaminetetraacetic acid (EDTA), nitrilotris(methylene)triphosphonic acid (NTTA), and trimethylenedinitrilotetraacetic acid (TMDTA). Experimental results showed an increasing complexing ability in the order of GCG < NTTA < TMDTA < EDTA, and an increasing selectivity toward the metal contaminants in the order of EDTA < TMDTA < GCG < NTTA. These results were largely consistent with equilibrium predictions. Enhanced recovery of metals from a very strong chelator EDTA was demonstrated with the use of metal-competing cationic precipitants (calcium hydroxide and ferric chloride) or anionic sulfide precipitant.