In 1927, Flaherty signed with the New York Yankees, a team that was part of the NFL at the time. His tenure with the Yankees was short-lived due to the team's dissolution, but it set the stage for his next opportunity. Flaherty then joined the New York Giants in 1928, where he would spend the majority of his playing career. As an end, he was known for his receiving abilities and defensive skills, contributing to the Giants' competitive edge during his time with the team.
Flaherty's playing career with the Giants was marked by several achievements, including helping the team secure the NFL Championship in 1934. His performance on the field earned him recognition as one of the top ends of his era. After retiring as a player, Flaherty transitioned to coaching, where he would continue to influence the game.
In 1936, Flaherty took on the role of head coach for the Boston Redskins, a team that would later relocate and become the Washington Redskins. Under his leadership, the Redskins won the NFL Championship in 1937, marking the franchise's first title. Flaherty's coaching style emphasized strategic innovation, including the introduction of the screen pass, which became a staple in football tactics.
Flaherty's coaching career with the Redskins lasted until 1942, during which he led the team to another NFL Championship in 1942. His ability to adapt and implement new strategies was evident throughout his coaching tenure. After leaving the Redskins, Flaherty continued his coaching career with the New York Yankees of the All-America Football Conference and later with the Chicago Hornets.
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