A triskelion‐shaped triradical triindeno[1,2‐a:1',2'‐g:1'',2''‐m]triphenylen‐7‐yl (1) and its internally fused derivative obtained by oxidative cyclization (2) were prepared in a straightforward synthetic sequence. Both compounds were confirmed to be triradicals and to possess intramolecular antiferromagnetic exchange interactions between spins, displaying a spin‐frustrated doublet ground state with doublet‐quartet energy gaps of −0.14 kcal/mol for 1 and −0.06 kcal/mol for 2. Despite their open‐shell character, they were sufficiently stable to be handled under ambient conditions on a timescale of days. Both compounds could be reversibly reduced to mono‐, di‐, and trianions and oxidized to 1+ and 22+, with strong NIR absorptions (1800 to over 3200 nm) observed for all open‐shell ions.