It’s a question most of the nation is asking again after yet another miserable failure, arguably the worst yet, as Roy Hodgson’s side were knocked out of Euro 2016 by the smallest nation ever to participate in the tournament.
But this should not have come as a surprise to those of us who have seen the same pattern repeated over the years, the pointless journey from hope to hopeless and back again.
The processes are repeated – sack the manager, wheel out a Five-Year Plan, crank up expectations before the next big tournament and then watch them fail.
It’s like watching a once-great footballer become an alcoholic, go to rehab, announce he’s feeling fit and well again, and then fall off the wagon – time and time again. Ring any bells, Gazza?
The landscape in English football changed in the 1990s, with the Premier League, Sky Sports, technical players and innovative coaches from abroad.
The new poster boys were Zola, Bergkamp and Klinsmann – intelligent, stylish and modest, on and off the pitch, and they could not have been more different to the bulldog breed English fans loved.
Arsene Wenger introduced new coaching methods, bringing science and skill to the teams he produced, and some others followed suit.
But with England and their fans it was always about rolling up your sleeves and getting stuck in. We got stuck in, alright.
Stuck in a rut that we have never got out of, a relentless cycle of optimism, failure and despair that keeps going round, whoever is in charge, however good the players.
Look at the list of talented players England have had to call on over the past 25 year or so – Gascoigne, Shearer, Sheringham, Scholes, Beckham, Gerrard, Lampard, Terry, Cole, Ferdinand – some of the most talented and decorated players in the world.
But they won nothing with England and rarely even came close.
While football in England moved on, English football did not.
Sure, there were flirtations with innovative coaches – Terry Venables took them to within a studs’ width of winning Euro ‘96, while Glenn Hoddle’s brilliance as a coach was fatally undermined by his failings as a man-manager.
Ultimately, the FA chose Hodgson because he was a safe pair of hands, who could bridge the gap between grassroots coaches and elite managers, and highlight the coaching ethos the FA were trying to promote with the building of St George’s Park.
This, they hoped, would make up the huge deficit in qualified coaches in England compared with other leading nations.
Spain and Germany have around six times the number of qualified coaches, Holland and Italy considerably more, and although the FA are trying to make up the numbers quickly, they do not make it easy.
I did my basic badges over 25 years ago, but to be able to go to a higher level would mean taking time off work and spending a fair amount of money.
I stopped coaching at my local club this year, exasperated by the cancellations because pitches are so poor, apathy from some of the kids, and the frustration of trying to teach young men who think they know it all.
But I know some of this England squad well enough to appreciate they all have the hunger and desire to improve – look at the work Harry Kane has put in over the last few years in order to make such massive strides.
But at this tournament Kane has looked a shadow of the Premier League’s top scorer, his touch and confidence gone.
Maybe it is sign of fatigue – he did play every game of the European under 21 tournament last summer, so has barely had a break in two years.
Maybe Greg Dyke, the outgoing chairman of the FA, was right to target Qatar 2022 as a chance for England to win something.
It will be bang in the middle of our season, when players are at peak fitness but without the fatigue of a long season. Will that be enough, though?
England have not gone beyond the quarter final stages for 20 years, have won only a handful of games at major finals in that time, and are currently without a manager or a masterplan.
They have fans that think another 1966 is just around the corner, a media that builds up the players only to knock them down, and a lack of structure from grassroots upwards that stifles talent.
No wonder I expect to be asking the same question for years to come: why can’t the English succeed at the game they gave the world?
“If you look at the way Arsenal play, they have a structure to the team. Arsene Wenger is under scrutiny for not winning things at Arsenal and people will disagree with me backing him for the England job, but you need a bit of everything in a football team. That blend is crucial. England have strength, passion, desire, hunger, and bullishness. They are strong-minded and resilient. But England need structure. They need guile and finesse.
England don’t play with any kind of cleverness currently. When they fall behind they launch it into the channels and can’t wait to get away from their own goal, just like they do in the Premier League. At this level you need to keep the ball and control games. That is what Arsene Wenger’s teams do.”
“It was pretty pathetic. There was a lot of hype coming into the tournament about our young, energetic youngsters, our players aren’t as good as we think they are. It was awful to watch, we were clueless. We were out-fought, out-battled, their tactics were better than ours, and everywhere you looked on the pitch it was pretty embarrassing. Gareth Southgate fits their remit, he has been with the U21s, he has been around the squad, so I would back Gareth Southgate if he was to go in there. But I would also look at getting experience around him like Glenn Hoddle.”
“My personal choices are… Mourinho (but it’s) three years too soon. Or Slaven Bilic, who knows the country, knows international management, with an attractive style of play. Plus he’s a massive Anglophile who knows what we expect from the players.
“Neither are English, neither are available, so we will go for Southgate or similar. Which will turn long-suffering England fans off again. We’ll win our World Cup group having played nobody and the boom and bust cycle will continue.
“Where was the promise of talent development at St George’s Park? Pearce, Ferdinand, Wright, Shearer, Sheringham, McManaman, Fowler, Cole, damn even Collymore invited to coach, learn, and get involved with the national set-up? ... So we will continue to lurch from English coaches who aren’t good enough to foreign mercenary (Sven and Capello came for the dough) who promise a lot but deliver little.”
“The worst defeat in our history. England beaten by a country with more volcanoes than professional footballers. Well played Iceland.
“England: Decent players, not great players. Poorly coached. Tactically inept. Every player perfectly confused. No belief in plan or system.
“Italy: Decent players, not great players. Brilliantly coached. Tactically astute. Every player perfectly drilled. Belief in plan and system.”