His ball control skills made him one of the most talented players in the country, but his individualism and outspoken nature limited him to only five England caps in a six-year international career.
He spent the war assembling aircraft radios and playing for Bradford PA, and was sold on to Second Division rivals Newcastle United for a £13,000 fee in October 1946.
He scored six goals on his Newcastle debut, but fell out with the club's directors, and was sold on to Sunderland for a British transfer record fee of £20,050 in February 1948.
He scored 97 goals in 320 First Division matches for the club, with the closest he came to a trophy being the 1949–50 season when Sunderland finished third in the league, and when they reached the semi-finals of the FA Cup in 1955 and in 1956.
[5] Arsenal's secretary-manager George Allison heard of Shackleton's talents, and drove to Bradford to sign him to amateur forms in 1938.
[8] Following this disappointment he took a job at London Paper Mills in Dartford, and turned out for the factory's works team in the Kent League.
[13] He began to avoid his shifts in the pits, and so was called into the Royal Air Force, where he served the remainder of his national service.
[14] He scored four goals in seven Second Division matches at the start of the 1946–47 season, but left the club in October 1946 after growing tired of heckling from his own supporters who did not appreciate his individualist style.
[18] However his return to Park Avenue in his fourth game for Newcastle was not a happy one, as he had a penalty saved by former teammate Chick Farr in a 2–1 defeat to Bradford PA.[19] The "Magpies" boasted a devastating forward line of Jackie Milburn, Roy Bentley, Charlie Wayman, Shackleton, and Tommy Pearson, and totalled 95 league goals in the 1946–47 season, though their tally of 62 goals conceded and 13 defeats left the club having to settle for fifth place.
[21] After the semi-final game he and club captain Joe Harvey went on strike over housing issues; the club's board eventually relented and granted Shackleton the house they had initially promised him, though to save face told the press that Harvey and Shackleton had been in the wrong and had apologised.
[22] He further came into conflict with the club at Christmas 1947, when he and goalkeeper Jack Fairbrother refused to join the squad on a scouting party on opponents Charlton Athletic, who they faced later that season in the third round of the FA Cup.
[32] Shackleton felt that a surprise home defeat to Manchester City on 15 April was both decisive and galling, as teammate Jack Stelling twice missed a penalty in a 2–1 loss.
[37] He was dropped and replaced by Stan Pearson for England's next game, before making a surprise return in a 1–0 win over Wales at Villa Park on 10 November 1948.
[39] He put in his finest performance however in his final England appearance, scoring with a chipped goal in a 3–1 win over the then World Champions West Germany on 1 December 1954.
I felt a keen sense of satisfaction – not because the goal made our victory over Germany certain, but because I had decided exactly how to go about scoring it long before the chance presented itself.
"[42] A showman who liked to entertain the crowd, he was able to cut the ball with sufficient spin that it would roll towards an opponent only to stop and then return to him as though on a string.
[43] On one occasion, 2–1 up against Arsenal with 5 minutes to go, he dribbled the ball into The Gunners' penalty area before putting his foot on it, pretending to comb his hair while looking at his watch.
to foreigners, because his fame was spread around Europe by the legendary "anarcho-folk-punk-band" Chumbawamba in their "Song To Len Shackleton" (released 2002 on their "Readymades" CD) Source:[51]