After school in 1926 he joined the original AFL's LA Wildcats team before playing end with Red Grange's New York Yankees in 1927 and 1928. After this Yankees franchise folded, Ray played in the NFL for the New York Football Giants.

After his playing days were over he took the job of coaching the Boston Redskins in 1936 and in his 7 seasons at the helm, his Redskin teams won two NFL Championships and four division titles. We have to keep in perspective George Halas and his Chicago Bears were the dominant force in the NFL during this era. Despite the powerful Bears Flaherty's squads defeated the Chicago teams in 2 out of 3 NFL championship games where they opposed each other.  

Coach Flaherty was also an innovator as he introduced a couple of significant items to football, the screen pass behind the line of scrimmage and the two platoon system where one group specialized in passing and the other in the run game.

Mr. Flaherty left the Redskins after the 1942 NFL Championship win to serve his country during World War II. After the war Flaherty returned to coach the New York Yankees in the brand new All American Football Conference and quickly guided the Yanks to two straight AAFC titles. He coached his final season in 1949 with the AAFC's Chicago Hornets and closed the brilliant coaching career with a record of 80-37-5 and an awesome .676 winning percentage! The Pro Football Hall of Fame enshrined this great coach in the entry class of 1976 as a coach.