In this interview, astronomer Massimo Stiavelli discusses his involvement with the Hubble and James Webb Space Telescopes. He recounts his early childhood growing up in Italy, higher education at the Scuola Normale Superiore in Pisa, and his interest in elliptical galaxies. He reflects on his time as a postdoctoral researcher at Rutgers University, his time at the European Southern Observatory, and his role deriving signs from the Hubble Space Telescope’s aberrated data. Stiavelli discusses his position with the European Space Agency in Baltimore, along with the initial developments of the Next Generation Space Telescope. He also offers his perception on the Space Telescope Science Institute and the scientists working there. He recalls his early involvement with the NGST’s Science Working Group, his role as Project Scientist, and his perspective on the growing schedule and budget delays that led to Congressional hearings. Stiavelli also recalls the impact of the Covid-19 pandemic on the final stages of Webb’s development, the launch, and its current operation. The interview concludes with an overview of Stiavelli’s views on the future of cosmology and the impact of JWST.