Born in Swansea in 1932, he made his debut for his hometown Club, Swansea Town (now City) in 1952 before joining Tottenham Hotspur four years later. By then he was a regular in the Welsh international side and travelled to Sweden for the 1958 World Cup, scoring the all-important winning goal against Hungary that put Wales into the quarter final where they were knocked out by Brazil, the only goal of the game coming from an unknown 17 year-old called Pele. Medwin was famously a vital part of the 1960-61 ‘double’ side, won an FA Cup winners medal in 1962 and would go onto make 197 appearances and score 65 goals for Spurs before breaking his leg in their 1963 end of season tour of South Africa. Fractured in three places, Medwin tried for 18 months to regain his fitness at White Hart Lane but would never play again.
It was in the New Year of 1965, following the departure of Manager Dick Moss, that Medwin was first spotted at Theobalds Lane and, along with Midfielder and PE Teacher Graham Briggs, managed the first team training sessions for the remainder of the season. Whilst popular with the players, Medwin’s priority (he was a Father of six) was securing an insurance settlement and a release from his Tottenham contract. Cheshunt were initally unable to offer him a full time salary, so Medwin publicly applied for the vacant Managers posts at both Swansea and Southern League Bexley United, but a combination of no replies and a revised offer from Cheshunt’s Chairman, Frank Davies, saw him placed in charge of the Ambers 1965-66 campaign.
Coupled with the arrival of a bombastic new Cheshunt President, Roy Stewardson, Medwin’s side got off to a good start in the league, losing only one of their first twelve games. However two defeats, an 0-8 exit to Wycombe Wanderers in the FA Cup and a 1-5 reverse at lowly Kings Langley in the Amateur Cup, were not well received. By November, he had used 25 players and, when his judgement was criticised by Stewardson for giving debuts to teenagers John Pyatt and Eddie Sedgwick, Medwin offered his resignation. Initially persuaded to carry on by Davies, Medwin finally snapped and resigned, with his last game in charge being an unremarkable 0-0 draw at Tilbury on November 29th 1966.
Coach Don Archer took the side for the rest of the season, narrowly avoiding relegation, whilst Medwin went on to take up coaching positions at Cardiff and Norwich before becoming John Toshack’s Assistant at Swansea City, who then famously climbed all four divisions of the Football League in the late 70s and early 80’s.
Terry Medwin was Cheshunt’s first ‘big name’ Managerial appointment, winning promotion in his first full season along with a County Cup, only to be then poorly treated by an impatient President, resulting to his premature departure. His judgement, questioned at the time by Stewardson, was vindicated when John Pyatt was watched and then signed by Bill Shankly for Liverpool and Eddie Sedgwick went onto become Cheshunt’s all-time leading goal scorer.
