Taylor played for his hometown club Bristol Rovers as an apprentice (in 21 league matches, scoring twice) before he was signed by Liverpool manager George Patterson for £5000 plus Ted Hartill in March 1936, he made his debut on the 28th of the same month in a league game at the Baseball Ground, Liverpool shared the points with Derby County in a 2–2 draw with Taylor scoring a late equaliser, his first goal for the club.
Taylor joined Liverpool as a young inside-forward with a lot of potential, but was reverted by George Kay to wing-half in which position he developed into a stylish, composed defender.
England legends Tom Finney, Stan Mortensen and Tommy Lawton made it a memorable day for Taylor, scoring the goals in a 3–0 win.
Taylor took over the reins with a determination to put Liverpool back where they belonged, immediately signing Alan A'Court, Tommy Younger, and club legend Ronnie Moran who ended up spending five decades at Anfield.
They included striker Roger Hunt, given his debut by Taylor in 1958, who spent 11 years at Anfield and scored 286 goals, and was also a member of England's World Cup-winning side in 1966.