Radical stabilization energies (RSE)s have been calculated for a variety of boryl radicals complexed to Lewis bases at the G3(MP2)-RAD level of theory. These are referenced to the B==H bond dissociation energy (BDE) in BH3 determined at W4.3 level. High RSE values (and thus low BDE(B==H) values) have been found for borane complexes of a variety of five- and six-membered ring heterocycles. Variations of RSE values have been correlated with the strength of Lewis acid–Lewis base complex formation at the boryl radical stage. The analysis of charge- and spin-density distributions shows that spin delocalization in the boryl radical complexes constitutes one of the mechanisms of radical stabilization.