Date: 26th April 2017 at 5:29pm
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With five FA Cups, three EFL Cups, two European trophies and (at least) four Premier League titles, will retire as the club’s most decorated player this summer.

Many sceptics would, of course, cite Russian oligarch Roman Abramovich’s takeover of the club as the main catalyst for Terry’s legacy. Regardless of opinion, all should appreciate the truly English football pedigree he brought to Chelsea once he was established in the side.

Indeed, the most successful teams of the Premier League era have successfully blended continental flair with bulldog spirit, and it is a trait which remains criminally overlooked by some managers even today.

From Senrab to SW6

Terry’s youth CV should be all the indication anyone needs of the potential he possessed from an early age. Playing for Senrab – a youth side that commanded the fear, respect and awe of junior football in the early 1990s – was as good a start as Terry could have been bestowed by the fates.

At Senrab, he began life as a central midfielder in front of a rock-solid defensive partnership of Sol Campbell and Ledley King – all three would become England internationals in time. Inevitably, like so many of London’s greatest youth talents, the incomparable West Ham youth setup was his next port of call.

Then, in 1994, a 14-year old John Terry made the move that would alter the course of history, signing schoolboy terms with Chelsea.

New Millennium: New Hope

As the final decade of the twentieth century dawned, Chelsea FC was a humble club with a stadium end that doubled as a car park. Capitalising on its status as founder member of the Premier League, the West London club grew almost unnoticed – as did the stadium in which it plied its trade. That growth culminated in F.A Cup triumph in 1997, which was then followed by victory in the Cup Winners Cup a year later.

This paved the way for a new era of unprecedented promise for Chelsea FC after years of obscurity. On 28 October 1998, Chelsea met Premier League leaders Aston Villa in the Football League Cup. Traditionally, the early matches of the competition are low-key affairs for Premier League teams – especially those involved in European competition, as both Chelsea and Villa were in 1998/99.

Yet, with the two teams flying high in the Premier League, this encounter would be an early indicator as to whether (or not) either side truly had the spirit and determination to be English champions.

Neither ultimately did, with both clubs ending the season bereft of silverware – but the night, at least, was Chelsea’s. With home advantage, the Blues roared to a 4-1 lead in the latter stages of the match. This provided player-manager, and hat-trick hero, Gianluca Vialli with a golden opportunity to blood an 18-year old Terry.

Given the scoreline and time remaining, it was hardly a stretch for the youngster against Villa’s lesser hitmen – including future England international Darius Vassell. However, Terry’s composure was self-evident from the off, giving Vialli much food for thought.

For Terry there would be one more appearance, a start in a 2-0 F.A Cup win against Oldham Athletic, before embarking on a make-or-break loan spell at Nottingham Forest in 2000. Six loan appearances for the two-time European Cup winners was all the indication that Chelsea’s new manager, Claudio Ranieri, needed to justify his instalment into the regular starting XI.

Coming of age in Y2K

After winning the Community Shield, Chelsea had begun 2000/01 in disastrous fashion. In what was very much a development that foreshadowed events fifteen years later, the Blues occupied a place in the relegation zone after a 2-0 home defeat to table-topping Leicester. This was the cue for future Foxes hero Ranieri to replace Vialli and give John Terry a run in the first team.

With a fearless nature that is seldom emulated today, Terry proved more than a match even for cultured, international-level strikers seven or eight years his senior in 2000/01. Chelsea’s form improved drastically, and by the season’s end, he was undisputedly the club’s player of the year as the Blues’ finished a respectable, if slightly disappointing, sixth.

It would be during the 2003/04 season, alongside William Gallas, that Terry would make the transition from first team regular to captain. With an open chequebook now at Ranieri’s disposal, Premier League markets showed drastically shortened title odds for Chelsea.

Ranier’s men finished second behind Arsene Wenger’s band of “Invincibles”, but qualified for the Champions League once again. However, it was not enough for Abramovich, and Ranieri became the first victim of the Russian oligarch’s hair-trigger axe.

Aided by the dual firepower of newcomers Arjen Robben and Didier Drogba, Chelsea swept majestically to an as-yet unbeaten record total of 95 Premier League points in 2004/05. With Terry now at the prime of his career, much of Chelsea’s first title win in half a century could also be attributed to his miserliness in defence.

Under Jose Mourinho, the Blues conceded just fifteen goals en-route to the first of the club’s four Premier League titles to date.

West end drama

After once more helping his side break the 90-point barrier in 2005/06, the second half of the 2000s decade would prove a relatively difficult time for John Terry. Periods of injury would follow, as Chelsea FC conceded its crown to Manchester United in 2006/07.

Silverware came in the form of two F.A Cups (2007 and 2009) and a Football League Cup (2007), but it meant nothing to a Chelsea side that craved true, long-term supremacy over the highest domestic and European honours. Manchester United once more enjoyed a spell of Premier League dominance and Chelsea would be continually frustrated in European competition.

For Terry, tears of despair were given an international presence in 2008, when Chelsea experienced penalty shootout heartbreak to (of all teams) Manchester United in Moscow, as the Red Devils won the Champions League for a second time under Sir Alex Ferguson.

As Chelsea’s most rewarding decade was coming to a close, Terry’s own problems reached a peak. Details of an alleged affair between Terry and former teammate Wayne Bridge’s now-former girlfriend Vanessa Perroncel began to emerge, culminating in the temporary loss of his international captaincy.

On the pitch, the frustrations of Terry’s team also reached an (equally) unforgettable peak in April 2009, as Chelsea bowed out to Barcelona in the Champions League semi final on away goals. Famously, in the most colourful of terms possible, Drogba bellowed his distaste at a “disgrace” of a refereeing decision down a camera lens to a worldwide audience.

2012: Terry is reborn

With Terry by now something of a figure for ridicule in popular football culture, it seemed as though Chelsea’s best chance of European glory had gone. But three years later, on 18 April 2012, Chelsea would enact sweet vengeance at the same stage of the competition, granting the Blues a golden opportunity slay the ultimate hoodoo.

Once more, Barcelona awaited Chelsea in the semi finals of the Champions League. Chelsea FC had endured its poorest season in recent history, occupying sixth place under Roberto Di Matteo despite boasting some exceptional talents. By contrast, Barcelona were reigning cup holders, boasting an unstoppable Messi alongside future Arsenal talisman Alexis Sanchez, and the unplayable Tiki-Taka trio of Xavi, Sergio Busquets and Andres Iniesta.

With the stakes stratospheric, both sides spent much of the first half cancelling each other out. Terry, now approaching the twilight of his career, was once more playing like the peerless field marshal of 2004/05. Alongside Gary Cahill, he resisted wave after wave of attack from (many would argue) the best attackers in the entire world.

Yet, a goalless draw was of little help to either side, and Stamford Bridge needed a hero. Inevitably, it was Didier Drogba, the man who had fired Chelsea to a record-breaking points tally seven years previously, who obliged. Ramires played in a beautiful cross, and Drogba swept home with his left foot to send Stamford Bridge into raptures.

Terry, now in the advanced years of his career, could have been forgiven for tiring in the second half. Not once was such fatigue evident though, and the deserved 1-0 result that would be followed by a 2-2 draw at a pulsating Nou Camp.

The rest, as they say, is history. Chelsea went on to draw with Bayern Munich on hostile turf, despite being outplayed for the entire final. The ensuing penalty shootout resulted in Chelsea atoning for the penalty defeat to Manchester United four years previously, and granted the West London club its first ever European Cup.

Where next for Mr Terry?

At present, retiring players have one of two mainstream choices: to take the plunge and enter management, or opt for a lifetime of media work. For instance, Monday Night Football is now blessed with the presence of Jamie Carragher and Gary Neville, two professionals who were once sworn enemies on the pitch. Therefore, they are more qualified than most to analyse the intricacies of the postmodern era.

One must, however, take the latter as a warning example to would-be managers going directly into top level management. In prematurely taking a hotseat, Neville’s CV is now permanently tarnished by a disastrous spell at Valencia.

For Terry, any entry directly into management would pose a similar risk. Although the lure of a newly-rich Chinese Super League may tempt his hand, Terry’s leadership is built purely for an English game, which always purports itself to be direct and uncompromising.

The most likely outcome will be Terry staying put at Chelsea in a coaching capacity – possibly until he is carried out in a box. But there is still a future management opportunity for Terry, when one considers club owner Roman Abramovich’s infamous propensity to swing the proverbial ‘axe’ without due warning or hesitation.

Regardless of his self-evident management skill, Antonio Conte – or even his successor – will one day experience a less-than-stellar season, and this could be the cue for yet another inimitable Abramovich execution.

When Conte, or his successor, bears its fatally incomparable brunt, a reversion to ‘boot room’ politics, as glorified in the 1980s by Liverpool, could be seen as the way forward, once Abramovich has become sufficiently disillusioned with continental managers. With only a true ‘son’ of the club then eligible for the big job, Terry may well find himself in the Stamford Bridge hotseat sooner than people can possibly expect.

Tamhas Woods holds a Masters degree in sports broadcast journalism and several years experience in sports writing.