Sam Wallace: Roberto Di Matteo not the right man for major rebuilding job at Chelsea

Talking Football: Chelsea should recall that Avram Grant was one penalty away from European Cup victory

The bookmakers have Chelsea at the longest odds of all four Champions League semi-finalists to win the competition. It would, admittedly, take two further monumental performances that they simply may not have in them. Tomorrow's second leg comes at the end of a draining 10-day, four-game run. Even in spite of the players who were rested, they looked like they were running out of steam at the Emirates on Saturday.

But the question remains: where does it leave Chelsea if they win the Champions League next month?

Don't dismiss it. After a weekend which ended with Newcastle United three points clear in fourth place; Real Madrid beating Barcelona at the Nou Camp for the first time since 2007 and Harry Redknapp having won just one league game in the last nine — just as the Football Association prepares to appoint the next England manager – no one needs reminding that form is an elusive property in football. It comes and it goes with remarkable consequences.

A Champions League trophy for Chelsea on 19 May would mean the club were faced with an extraordinary decision on whether a caretaker manager, whose appointment was never intended to last beyond the end of the season, might have to be given the job permanently. If only for the trifling reason that Roberto Di Matteo will have just delivered the club and its owner the one trophy they had spent nine years and the best part of £1bn trying to win.

No one would argue that this Chelsea team is anything like as good as it has been over the last five years, yet they could win the biggest prize of all. Football occasionally presents anomalies like the trophy at the end of a bad season or the slump no one expected. No individual, however good, is immune to the bad moments. If Lionel Messi can get sidetracked into an argument with Alvaro Arbeloa, as he did on Saturday night, and end up frustrated and defeated, then it can happen to anyone.

Redknapp's terrible run of results is a concern but that does not nullify the experience, the track record and the qualities that so evidently make him the best-qualified man for the England job. One need look no further than Alan Pardew's managerial career for the perfect example of why one should strive to see the bigger picture rather than make snap judgements on individuals.

If Chelsea eliminate Barcelona tomorrow, and go on to win the final in Munich, the point still stands that they need to change. That whatever new era is being ushered in this summer cannot be delayed or postponed simply because they stumbled upon the European Cup.

If Di Matteo, admirable though his effort has been, was not considered ready to do the long-term rebuilding job as manager last summer, then common sense would dictate he would not be the man to continue next season. But it goes deeper than just Di Matteo's future. This season could end in Chelsea being European champions, it could end with them in the Europa League. Either way, it feels like a watershed.

It was enlightening to read the reasons Txiki Begiristain, the Barcelona technical director for seven years until 2010, gave for not joining Chelsea when he left Barça. "It's not enough to have a technical director who only deals with the academy and grassroots work; he's also got to be able to influence the first team as well and be able to take the vision forward," he said in an interview with The Times last Saturday.

"It's pointless having a technical director getting the grassroots football to go in one direction... if the first-team coach does not agree with those ideas. All that is what I conveyed to them [Chelsea] at the time, but in the end it was something that we couldn't agree upon."

It shone a light on a disconnect at the heart of Chelsea which has been detectable since Jose Mourinho's last full season in 2006-07. Besides the six managers – temporary and permanent – who have come since Mourinho, there has been Frank Arnesen, the former sporting director, the various advisers and then the prerogative of Abramovich himself to shuffle the pack. The current technical director is Michael Emenalo. He appears well-liked but little is known about him outside the club.

It is the misfortune of the Abramovich years that they tend to be remembered for the bad signings and the managerial appointments that, for too many reasons to list, went wrong. The three Premier League titles, each one remarkably hard-won, get overlooked. In the case of the first, Chelsea won it against arguably the best Arsenal team in history. In the case of the second and third, Chelsea won them primarily against Sir Alex Ferguson, the most successful title-winning manager of all.

In that context, it has not been a bad effort by Abramovich. His club gate-crashed one of the biggest cabals in English football's history and, once in there, they refused to leave. Comparisons with Manchester City, post-Abu Dhabi, are difficult to make because City's tilt at joining the elite began from a much lower base in 2008 than Chelsea's had five years earlier. But both clubs would agree that just spending a new-world billionaire's fortune does not alone lay the foundations for continued success.

Who the next Chelsea manager should be, how the club should function – those are separate arguments. Safe to say that even if Chelsea become European champions next month, that does not mean the current system is vindicated or even that the current manager is the man for the future. If Chelsea need any more convincing why that should be the case, they need only recall that Avram Grant was one penalty kick away from winning the competition.

Walcott is still hamstrung by the weight of expectation

It is not often that Arsène Wenger criticises one of his own players, so when he reprimanded Theo Walcott for not coming off earlier with a hamstring problem at the Emirates on Saturday it was worth taking note.

The injury now imperils Walcott's participation in Euro 2012, which is hard on him given he is yet to play at a major tournament for England, having been taken to the 2006 World Cup finals and never used and then controversially left out of the 2010 squad.

In Walcott's defence, he has been criticised in the past for coming off too readily. Overall it seems symptomatic of a young man still trying to establish himself among those at the very top of the English game, where it was always expected he would be. What is not in doubt is that if he were to miss this summer's European Championship it would be a cruel outcome for a player who has carried a weight of expectation for so long.

Sending cash home isn't just African issue

It feels like a cheap headline for an African footballer, but Papiss Cissé's revelation that his wages support 70 people is not uncommon. I interviewed Emmanuel Adebayor this season and he was quite upfront about the imperative of earning as much as he could because so many people relied upon him financially.

The mistake is to think that it is only African footballers who find themselves in that situation. There are many footballers, some of them still on their first professional contracts, who are the key breadwinners for their families.

I have heard some horror stories about the bad decisions that are made in a teenage footballer's career because the family chases the money. Talk to people at academies and the good football agents and they will tell you the same.