In order to extend the physical length of hole delocalization in a molecular wire, chromophores of increasing size are often desired. However, the effect of size on the efficacy and mechanism of hole delocalization remains elusive. Here, we employ a model set of biaryls to show that with increasing chromophore size, the mechanism of steady-state hole distribution switches from static delocalization in biaryls with smaller chromophores to dynamic hopping, as exemplified in the largest system, (tBu)HBc(2) (i.e., "superbiphenyl"), which displays a vanishingly small electronic coupling. This important finding is analyzed with the aid of Huckel molecular orbital and Marcus-Hush theories. Our findings will enable the rational design of the novel molecular wires with length-invariant redox/optical properties suitable for long-range charge transfer.