World Cup 2014: Roy Hodgson faces defining period as England manager with Raheem Sterling rising in value

England manager’s long career will be in the balance in Brazil but over 38 years he has shown a willingness to take gambles

The England squad pose for a photo at Luton Airport yesterday before taking their flight to Florida (PA)

The forecast is for clouds in Miami this week, with Roy Hodgson apparently doomed to take an English summer with him wherever he goes, from the Algarve to Florida, where his players arrived on Sunday – the penultimate step on the long journey to Rio de Janeiro. It is getting closer to what will be the biggest month of Hodgson’s managerial career and, whether he likes it or not, the period upon which history will judge him.

From Croydon to the Copacabana over 38 years, and 20 jobs in management. In one of his press conferences on Thursday the son of south London was asked about his roots – the BBC are planning to produce a documentary on him – and Hodgson answered in that slightly overly formal manner of his that he was very proud to be a Croydon boy, although even he seemed at a loss to define what that might represent.

That has always been the difficulty of getting to the essence of Hodgson the manager. There was no reference point from his playing career, which passed at such a low level that there does not even appear to be any film footage in existence of those days. In terms of his management, his mentor was arguably his friend Bobby Houghton, the man who got him his first job and even more of a mystery to the English football public than his more successful protégé.

Most of Hodgson’s career has passed without being scrutinised by the English, until its most recent years. He acknowledges as much and is fond of a joke at his own expense. Last month he was reminiscing about his days as the Switzerland manager taking the team to the 1994 World Cup finals – as fine an achievement as any of his – and remarking that looking back now, he recognises how “amateurish” their approach was to the tournament.

Put plainly, Hodgson is regarded as a conservative. It is not entirely undeserved, given his high-profile jobs in England when he has been more successful with underdogs like Fulham and West Bromwich Albion than big dogs like Blackburn Rovers (as they were in the late 1990s) and Liverpool. But in his first managerial job at Halmstads he was no traditionalist; he was a radical who tore through the conventions of Swedish football; helped develop many of the players who were so successful at the 1994 World Cup finals and went on to greater success at Malmo from 1985.

At FC Copenhagen, where he spent just one year from 2000 to 2001, the hierarchy acknowledge that he laid the structure for the modern-day club that has enjoyed such domestic success in recent years.

The decisions that define Hodgson at this World Cup finals will be marginal. He is never, for instance, likely to field Raheem Sterling, Ross Barkley and Alex Oxlade-Chamberlain in one starting line-up – few managers would in his situation. But he may well decide to play at least one, and again on Friday night against Peru he was given reason to believe that the one could be Sterling. The boy from Wembley is playing with the fearlessness that changes games. He does not care who he is playing against, and it shows.

It was in the position that Wayne Rooney played for 66 minutes at Wembley that the Liverpool player was introduced on Friday, and in place of the man whom Paul Scholes has dared Hodgson to drop. Early days yet for Manchester United’s Rooney, who was playing his first football match since 26 April, but you could hardly take your eyes off Sterling. Perhaps he is best for that role, attacking tired defenders, drawing mistakes at the end of games – but there comes a stage when he just has to play.

Where that would be is a question Hodgson has been unprepared to answer so far. He bridles at any attempt to pin him down, presumably with one eye on his line-up for Italy, but when it comes to Sterling, he will not even disclose the position he believes suits the player best. Did he know? “Not yet but it would be foolish to say that, wouldn’t it? This [Peru] was only his third appearance and it would be stupid for me to say on the basis of just a few minutes ‘Raheem Sterling: this is his best position’.

“I’m not even certain I want Raheem Sterling to have a ‘best’ position necessarily. I want Raheem to be able to play in the position where we need him. We thought it would be good to bring him on initially in the position behind the front player, in behind Danny Welbeck, where we’ve seen him play well. But then we wanted to bring Ross Barkley on so we moved him wide and he did OK there.

“He’s a good player and I’m sure he’s going to be a very big player for England going forward as well, but at the moment I would rather like to see some of these younger players treated with a little bit more caution. I think it’s very dangerous to start building them up and saying ‘England are going to do terrifically well because of them’. There’s a lot of other players in our squad who are going to have to take responsibility, and hopefully the younger players will come in on the back of it and put the icing on the cake.”

The “icing on the cake” reference was telling. The Sterling generation are, for now, the decoration on a confection that Hodgson wants to keep as straightforward as possible. He cannot afford to lose that first game of the World Cup against Italy on 14 June. As for the Italians, they start the penultimate week of preparation having to come to terms with losing the services of the midfielder Riccardo Montolivo, who broke a leg against the Republic of Ireland at Craven Cottage on Saturday.

With all his years of experience, Hodgson will know it is moments such as those, and the way a squad handle them, which often point towards the bigger picture of a team’s performance. Montolivo is by no means irreplaceable but he is important and the Milan man’s injury is one more thing to deal with. England have not yet had their first big blow to their preparation. Perhaps they will not have one at all.

At some point at this tournament, Hodgson will make the decisions that define his managerial legacy.

It may be something as yet unanticipated but he would only be human if he was wondering how far he dare push Sterling in his plans, and how the player will himself respond.