Regiodivergent C-C bond-forming reactions are a powerful tool for constructing diverse molecular architectures from common precursors. While transition metal catalysis has dominated regioselective transformations, achieving similar precision with transition-metal-free methods remains an unmet challenge, particularly when using identical starting materials. In this work, we report a transition-metal-free, regiodivergent direct alkylation of electronically unbiased pyridines using 1,1-diborylalkanes as the sole alkylating agent. The key to controlling regioselectivity lies in the choice of alkyllithium activator of 1,1-diborylalkanes: methyllithium directs alkylation predominantly to the C4 position, while