In the fall of 1969, a vacancy on the Celtics beat of "The Boston Globe" was created, and Ryan got the job. Ryan was hired by the paper's morning sports editor Francis Rosa. While covering the Celtics, Ryan developed a close relationship with the Celtics organization. Ryan would even go out to dinner with the team. Ryan sat at the press table eight seats from the Celtics' bench, where colleagues referred to him as the "Commissioner", not unlike Peter Gammons's nickname. Boston Sports Media critic Bruce Allen has said, "His passion is not faked."