Terry Venables might be better known as the manager who almost led England to European Championship glory during a summer when football ‘came home’, but to an older generation of Chelsea fans, he will forever be the larger-than-life captain of Tommy Docherty’s Diamonds, the moniker bestowed upon the promising group of players coming through at Stamford Bridge in the early 1960s.

It was quite the coup for the Blues to bring him to west London in the first place, as the Dagenham-born youngster was coveted by clubs throughout the capital during his school days. Chelsea finally secured the services of the boyhood Tottenham fan, just as they did with so many of the capital’s top talents around that time, thanks in no small part to the work of the larger-than-life club scout Jimmy Thompson and the clear pathway established between the Blues’ youth set-up and the first team.

‘Chelsea had a good name for bringing young kids through,’ Venables told Rick Glanvill for our official historian’s book Rhapsody in Blue. ‘Even as a kid you’re ambitious: you thought you’d get into the team at 17 or 18.’

He did just that, less than two years after arriving for his first day at the club in July 1958 alongside, among others, Peter Bonetti, Allan Harris, Bert Murray and Bobby Tambling. Harris and Murray were two he had struck up a firm friendship with on the schoolboy football scene; it was no coincidence the three of them ended up at the same club.

His leadership qualities were spotted early on as he was made captain of a youth team which won back-to-back FA Youth Cups. It was during the first of those triumphs that Venables both started training with the first team and was given his senior Blues debut, which came in February 1960 when he was aged 17. Ted Drake’s side were beaten 4-2 by West Ham United at Upton Park, squandering a two-goal lead in the process.

‘I think it’s fair to say I could have had a better start to my career, with nothing I tried seeming to work for me,’ Venables wrote of the game in his autobiography, Born to Manage.

He had started alongside Johnny Brooks, the former Tottenham Hotspur inside-forward who Venables had idolised and subsequently wished to emulate in terms of his composure, charisma and capability of splitting the opposition defence with a slide-rule pass.

While that was the only first-team appearance Venables made that term, his attention switched back to the FA Youth Cup, which we won for the first time in 1960 before retaining it the following year. By this time, he had become a regular in the senior Blues set-up, although ‘senior’ may have been a stretch; Drake’s Ducklings, as our title-winning manager’s young charges were known, started the campaign with a side boasting an average age of 24, a number which had decreased to 22 by its conclusion. The inconsistency – some would say naivety – of youth was apparent by the goals for and against tallies, which read 98 and 100 respectively.

It was clear, however, that the club had quite a player on our hands in the form of Venables, who took on the No4 shirt and looked to have all the qualities of a classic on-field general, dictating play from deep and directing players positionally. This was not a youngster lacking in confidence – he had, after all, displayed his showmanship over Christmas during his maiden full campaign in the first team by singing on stage at the Hammersmith Palais.

An even younger Chelsea side, shorn of its talismanic frontman Jimmy Greaves, struggled during the 1961/62 season and it was largely an unhappy campaign for Venables as he played only 12 matches. There was the highlight of his first-ever goal in senior football, which came in a heavy defeat at Cardiff City, but after featuring in Drake’s final game as Blues boss, replacement Tommy Docherty called upon Venables only three times as the club dropped down into the Second Division.

The following campaign saw the transition from Drake’s Ducklings to Docherty’s Diamonds, with Venables one of the major players as we immediately bounced back to the top flight, playing every minute of our 42 league matches that term. A penalty on the final day – the first of eight successful conversions from the spot in the league during his Blues career – in a handsome victory over Portsmouth secured our return to Division One.

Aided by his promotion to spot-kick duties, Venables became a regular name on the scoresheet for the remainder of his time at the club, but far more noteworthy at that time was his contribution towards dressing-room harmony. During the 1963/64 season he became club captain, a natural role for a player who was always the life and soul. Nearly all of his team-mates from that time spoke fondly of a man who loved a prank but, more than anything, always had the backs of those he led out onto the pitch every Saturday.

‘Terry was a leader right from the start of his career,’ said team-mate Barry Bridges, who came through during the same era. ‘When he was captain I suppose he was only 19 or 20, but he did more to lead the team than the manager. He was the guvnor on the pitch and it was no surprise to see what he went on to achieve as a football manager himself.’

Venables’ first full season as skipper, in 1964/65, was arguably the best of his time here. Not only did it include his only trophy won as a Blue, it also saw his club form recognised at international level. As a result of the two caps won for the senior side during the space of 49 days during the winter of 1964, he became the first man to be capped by England in schoolboy, youth, amateur, Under-23 and full internationals, although he would never play for his country again.

After scoring on the opening day of the campaign against Wolves, Venables added two more in consecutive games against Leeds and Arsenal which confirmed us as genuine title challengers. A penalty in the first leg of our League Cup final against Leicester City helped secure the club’s first-ever triumph in a major cup competition, but our bid for a domestic Treble came unstuck in the closing weeks.

With Venables and Docherty often at loggerheads – two jocular fellows who loved nothing more than to be the centre of attention – things came to a head with the infamous Blackpool incident, when the skipper was one of eight players sent home from an away trip due to breaking curfew. Though he was one of those to return for the final-day loss at Blackpool, the damage had already been done – both to our title hopes and the relationship between captain and manager, despite a brief reconciliation.

Winning the League Cup had gained us entry to the Fairs Cup the following season and the European stage seemed to suit Venables down to the ground. He scored a famous hat-trick against Roma in the opening round, which included a goal which would have been replayed time and time again had it occurred in the modern era. When a free-kick was awarded to the Blues, Venables made a song and dance of counting out 10 yards and then, having reached the wall, spun around to receive the pass before finishing with aplomb.

‘We worked things like that out beforehand,’ he said of that cheeky goal. ‘We were non-stop talking about football, like in the cafe in Fulham Broadway, for hours after training. Talking about what you could do, how you could get better.’

The hat-trick came at the end of a run of eight goals in nine games to begin that season, but he would not score again until March and the underlying problems with Docherty came to a head after our tepid FA Cup semi-final defeat to Sheffield Wednesday, when Venables was among those singled out for criticism by the manager.

Unfortunately, the damage this time was irreparable. The beginning of the end came in the away dressing room at the Camp Nou ahead of a Fairs Cup semi-final against Barcelona, when Docherty introduced the players to new signing Charlie Cooke. The story goes, as told by the manager, that Venners decided to test the new boy by throwing the ball to him; Cooke promptly caught it on his instep before juggling the ball, taking it on his neck and then flicking it back to Venables. That game in Catalonia would be his last in Chelsea blue.

‘I think I knew then,’ Venables conceded years later. ‘I got the hint when he was juggling the ball in the corner! Things had got to a bad stage. I didn’t understand at the time, but if someone’s got to go, it’s always the player. I’d always wanted to play for Chelsea and I loved it so much I wanted to be there all my career. I didn’t want to go.’

He left just a fortnight later, joining Tottenham Hotspur for a fee of £80,000 and a year later he was part of the side, along with Greaves, which beat their old team-mates in the FA Cup final.

Venables represented two more London clubs, Queens Park Rangers – losing an FA Cup quarter-final against the Blues in 1970 as we went on to lift the trophy for the first time – and Crystal Palace, before bringing down the curtain on his playing career in 1974 and embarking on a new chapter in football as a coach.

His last two clubs on the pitch were the first two of his managerial career, which hit new heights in 1984 when he took over at Barcelona. ‘El Tel’, as he was dubbed, brought a hard-nosed 4-4-2 to Camp Nou, where he was ably assisted by his old Chelsea team-mate Allan Harris, and won La Liga in 1984/85. However, they lost the European Cup final against Steaua Bucharest in Seville the following season.

He came home to London to manage Tottenham in 1987 and added another FA Cup triumph to the one from his playing days with the Lilywhites and he was also the last Spurs boss to beat Chelsea, in 1990, before our famous 12-year unbeaten run against our rivals.

Following this, Venables was given the honour of leading England at a major championship on home soil, as he was appointed manager two years out from the European Championship. His popular Three Lions side captured the hearts and imagination of the country as they reached the semi-finals of Euro 96 before suffering penalty shoot-out heartache against Germany.

Having left England at the end of the tournament, brief spells managing Australia, Crystal Palace, Middlesbrough and Leeds followed before Venables stepped away from football. The lure of assisting Steve McClaren during his ill-fated tenure in charge of England briefly pulled him back into the game, but both left their jobs with the FA following the failure to qualify for Euro 2008.

However, it is for the ability, determination and leadership he demonstrated on the Stamford Bridge pitch that he will forever be remembered at Chelsea. Rest in peace Terry.