Here, we adopt and expand a one-pot multicomponent ladderization approach to synthesize a diverse set of charged ladder molecules (Fig. ) bearing methylthio (-SMe) anchor groups for single-molecule electronic characterization. Our results demonstrate that ladder-type molecules with fused arene backbones exhibit a molecular conductance (dlog(G/G0)/dx ≈ -0.1 nm -1 ) that is independent of junction displacement x, in stark contrast to the nanogap-dependent conductance (dlog(G/G0)/dx ≈ -7 nm -1 ) observed for non-ladder analogs. In addition, molecular conductance through the ladder backbone is robust and nearly independent of the chemical identities of counter anions or substituent groups. Our computational results show that charged ladder molecules exhibit constrained torsional motion in their terminal anchor groups, which contributes to an exceptionally narrow conductance distribution during dynamic 'pulling' trajectories in STM-BJ experiments. In addition, ladder-type molecules offer enhanced junction conductance compared to their non-ladder counterparts, which is attributed to enhanced electron delocalization along the molecular backbone. Interestingly, our results show that positively charged ladder backbones can serve as electrostatic anchor points, facilitating voltage-regulated dual charge-transport pathways in ladder-type molecules. A combination of molecular simulations and chemical and physical characterization was used to understand the electronic properties of ladder-type molecules, including density functional theory (DFT) calculations, X-ray crystallography, electron paramagnetic resonance (EPR), superconducting quantum interfering device (SQUID) experiments, and cyclic voltammetry.