In conclusion we have synthesized a genuine analogue of the π-allyl cation replacing the typical carbonbased framework with three contiguous bismuth atoms. The synthesis of such a complex demonstrate the ability of very diffuse and large frontier p orbitals of heavy main group elements to effectively overlap similarly to their lighter congeners, thus allowing effective π-delocalization of electrons. Intriguingly, the molecular architecture of our bismallyl cation is characterized by two Bi-Bi bonds formally possessing a non-integer bond order. However, as expected when heavy main group elements are involved, the electronic description becomes more entangled due to SOC and relativistic effects. Indeed, according to our interpretation of the absorption spectrum the intensity in the red-region of the spectrum (around 700-900 nm) originates from triplet states that borrow intensity from their singlet counterparts by strong SOC mixing. This situation is highly characteristic of the heavy element bismuth which tends to break the established spin-and space selection rules that govern the properties of most complexes bearing lighter main group elements. In addition, due to the electrophilicity of the highly reduced (Bi)3 + core, the compound can be used to transfer a Bi(I) atom which provide a blueprint of reactivity for assembling materials and molecular architectures based on low-valent bismuth compounds. Overall, this complex expands the understanding of chemical bonding in this area of the periodic table and sets novel boundaries in the chemistry of main group elements towards conjugated systems.