This paper examines the academic paths of Freeman Dyson and C. N. Yang, along with their respective assessments of each other. It also explores their interactions with other physicists, particularly at the Institute for Advanced Study in Princeton with the Director J. R. Oppenheimer, as well as the assessments by Enrico Fermi, J. R. Oppenheimer, and Eugene Wigner when C. N. Yang was promoted to full professor. Additionally, it covers Freeman Dyson’s later recollections of P. A. M. Dirac, Richard Feynman, Enrico Fermi, Murray Gell-Mann, and others.