It was the summer of 2004. Chelsea Football Club had just finished runners-up to Arsenal in the English Premier League a their best league position for 49 years a and in the process, broken the club record for highest number of points won in a season. Despite that, Russian billionaire Roman Abramovich a still in the nascent years of his ownership of the club a made his first major decision by deciding to relieve Italian Claudio Ranieri of his managerial duties. Abramovich sought a man who could match his ambition and hunger for success a someone that could not only take on the established powerhouses of Arsenal and Manchester United, but take them on and win. Before long, he had found the ideal candidate.

Jose Mourinho exploded onto the English Premier League scene in June 2004 with his now-iconic press conference where he declared himself to be the a Special Onea . That sense of confidence rubbed off on his players, kick-starting an unprecedented era of success at Chelsea; the Portuguese won two Premier League titles, two League cups and an F.A. Cup in his three full seasons in charge, before leaving in somewhat acrimonious circumstances as the most successful manager in the cluba s history. The lure of the Premier League and life in London was perhaps too great for Mourinho, who returned to Stamford Bridge in 2013 after spells at Inter Milan and Real Madrid. A year on, the former translator from Setubal is on the brink of his third Premier League title. What lies beyond that, however, is Jose Mourinhoa s greatest challenge.

As another second-season Jose Mourinho side continues its inevitable march towards success, it is worth considering what the future holds for Mourinho and Chelsea. It is a well-known fact that the Portuguese has had his best successes during his second season in almost all of his managerial roles till date. Equally, his third seasons have failed to live up to expectations. At Benfica, Uniao de Leiria, Porto and Inter Milan, Mourinho did not stay beyond the second season, while at Chelsea and Real Madrid, his third season was marked by tension and animosity between himself and the hierarchies of the respective clubs, which translated to a lack of success on the pitch. As such, there has always been a question-mark over Mourinhoa s ability to sustain long-term success at a club.

There is a sense, however, that in his latest managerial position, things are a little different. The Bluesa boss said ahead of last seasona s Champions League semi-final against Atletico Madrid: a My future is Chelsea. Ita s Chelsea that decides when our relationship is over, not me. I want to stay forevera . It is something that Mourinho has repeated on several occasions since his return to the English capital, and if taken at face value, indicates a change in his mentality. By his own claims, he is a calmer, more settled manager, and one that appears ready to undertake an enormous challenge a the essence of which is to sustain success at the highest level with Chelsea year after year. A second-season Mourinho team is a familiar prospect. But what does a fourth-season or a fifth-season Mourinho team look like?

Sir Alex Ferguson is the greatest manager in Premier League history. What is most remarkable about him, however, is not necessarily his tactical acumen or the style of football his teams played, but his unrelenting desire to be successful season after season for the best part of three decades. Ferguson built teams, demolished them, and built better ones a all the while maintaining a level of success unparalleled in the history of English football. That, above anything else, is a true sign of his greatness. It is, of course, unlikely that Mourinho will be able to replicate the feat in terms of Premier League titles or the number of years at the job, but it is what he must aspire to in order to silence his critics.

The challenge is a unique one for Mourinho, but one that both he and the club appear ready for. Mourinho has won every trophy there is to win at club level, more than once. He has won titles in Europea s traditional top three football countries a England, Spain and Italy. The Real Madrid job is the absolute pinnacle in a managerial CV, and ita s something Mourinho can tick off. Chelsea, for their part, have changed managers with reckless abandon over the past decade, hiring everyone from Avram Grant to Carlo Ancelotti. Whilst Abramovich might point to the cluba s trophy cabinet, Chelseaa s success has come despite the frequent change in managers, rather than because of it. With most of the cluba s key players aged 26 or below, it is clear that Mourinho is building a team not just for the present, but one for a successful future. All indications are that the marriage between Chelsea and Mourinho is destined to be a longer, if not more successful one than the last time around.

As a club, Chelsea are just below the level of the true global elite a the likes of Real Madrid, Bayern Munich, Barcelona and Manchester United a both in terms of financial muscle and footballing success. The Blues, are, however, taking measures to bridge that gap. A new sponsorship deal with Yokohama Rubber will see Chelsea pocket A?40m a season starting 2015/2016 a the second biggest kit-deal in the history of English football. A stadium expansion has also been touted, after plans for an altogether new stadium were shelved, to significantly increase the revenue from gate receipts. It is something that could have a knock-on effect on the amount of money Mourinho has to spend on transfers, posing a threat to success on the pitch. This is, however, part of long-term management, and something Mourinho will have to work around to keep his team competitive at the highest level.

Mourinhoa  s Second Chelsea Stint Is His Toughest Challenge Yet

The possibility of expanding Stamford Bridge is being investigated by the club

Financial growth is driven, to a significant extent, by success on the pitch. Chelsea are now a global brand, a more recognisable institution than when Mourinho joined a decade ago, and that is largely down to the numerous successes the club have had over the past decade. Although Mourinho might not be able to directly bridge the economic gap between Chelsea and the football super-powers of the world, success on the pitch can go a long way towards doing so in an indirect sense. Winning the Champions League with Chelsea, in particular, is something that could help attract a new generation of fans towards Chelsea a growing the cluba s fan-base and consequently, commercial revenue. Taking Chelsea to that next level is a task of gargantuan proportions, and one that can only be accomplished through sustained success on the pitch at the highest level, season after season a unchartered territory for Jose Mourinho.

Mourinhoa s record of promoting players from the youth academy is another stick that his critics use to beat him with. Whilst it is true that the Portuguese has had success with young players, most of them have been bought for the first team given their level of talent. Promoting youngsters from the academy is not high on the list of priorities for a manager or a club intent on achieving instantaneous success, as has been the case with Mourinho and the jobs he has had so far. It is a good sign for the Blues, then, that their manager has made it explicitly clear on numerous occasions that he intends to integrate players from the academy into the first team in the coming seasons. Doing so successfully is another major challenge Mourinho is faced with, and yet another that is somewhat new for him.

The Chelsea academy has never seen better days. The players at the academy are perhaps the most talented bunch the club have ever had, with the young Blues reaching their fourth straight F.A. Youth Cup final this season, as also the final of the UEFA Youth League. The likes of Lewis Baker, Nathan Ake, Andreas Christensen, Ruben Loftus-Cheek, John Swift and Dominic Solanke have already made their senior bows under Mourinho, an encouraging sign for the future. Even though he has made bold statements to the effect that he would accept blame if some of these players did not become England internationals, Mourinho acknowledges that promoting youngsters is a difficult task given the demands of modern football.

Mourinhoa  s Second Chelsea Stint Is His Toughest Challenge Yet

Dominic Solanke has scored 33 goals for Chelsea this season. He could be the future for the club and the England national team.

Integrating academy players into the senior squad is, by all accounts, an imperfect science. It is imperative, however, that Chelsea capitalise on the talent they have within their ranks. Crucially, the overwhelming majority of this young talent is English. The likes of Ruben Loftus-Cheek, Lewis Baker, Nathaniel Chalobah, Isaiah Brown, Dominic Solanke, Charlie Colkett and Jay Dasilva amongst others have all represented England at various age-levels. With John Terry in the twilight of his career, the absence of another club-grown player in the first team is becoming ever more conspicuous, and it will fall upon Mourinho to ensure that that particular void is adequately filled. In a very real way, the level of success that Mourinho achieves in terms of nurturing these young players will have a major impact not only on the future of the club, but also that of the England national team years down the line.

The challenge facing Mourinho is enormous, but clear: keep Chelsea on the path of success season after season whilst promoting younger players from the academy into the first team, and attempt to elevate the club to the level of the biggest clubs in world football. He might not succeed, or even come close, but what is evident is that this undertaking requires time and stability. It requires the Portuguese to stay at the club for years, and for the club to play its part in ensuring that that happens, barring any extraordinary circumstances. The time has never been more ripe for either party.

Jose Mourinho has always been a trailblazer. Perhaps now, however, it is time to follow in the footsteps of the man he calls a the Boss of Bossesa a Sir Alex Ferguson. Mourinho has already left an indelible mark on Chelsea, and indeed, world football, but what he achieves in the coming years could see him recognised as a bona fide all-time managerial great.

What lies ahead is Mourinhoa s toughest challenge yet – but also his greatest opportunity.