Sir Bobby Charlton 

The legendary World Cup-winning midfielder was cited by many as England’s greatest ever footballer when he sadly passed away recently at the age of 86. He very likely was.

Management however simply wasn’t his forte, as demonstrated by a disastrous and brief stint in charge at Preston North End in the early Seventies that saw the club relegated in his first campaign.

Soon after, Charlton resigned from his post, aggrieved at a key player being sold.

With the ball at his feet and the goal 25 yards away there were few more ruthless in the game. Yet off the pitch, perhaps he was too much of a gentleman to succeed in a trade that requires a mean streak. 

Paul Gascoigne

Another legendary English midfielder, another failed gaffer, although in this instance Gazza’s problems away from football scuppered his managerial aspirations from the off.

A brief spell as player-coach in China was quickly curtailed when the ailing star flew to America to go into rehab.

A similar role at Boston United came to nothing when they refused to let him participate in I’m A Celebrity, Get Me Out Of Here just a few games in.

A subsequent spell at Kettering Town lasted barely a month when the board claimed he was turning up for training drunk. 

With the Poppies, he won two, drew two and lost two. In fairness, we can think of other coaches around today with inferior win percentages. 

Gary Neville

Whether you love him or hate him it has to be acknowledged that Neville talks a good game, knowledgably dissecting games and incidents for Sky.

In the dug-out though, that wealth of expertise proved no use at all, his time in Spain quickly descending into struggle, even farce.

An inability to speak the language didn’t help his cause, nor did the initial reception by the Valencia fans to his appointment.

The former Manchester United defender was brought in by the club owner Peter Lim, his good friend but distrusted and detested by the Los Ches faithful.

Then the poor results followed, the nadir being a 7-0 hammering at the hands of Barcelona.

“I just said English words and stuck an O on it,” he has joked since, and the football odds on Neville returning to the touchline anytime soon reside somewhere between none and slim.  

Hristo Stoichkov

“I don’t believe in tactics,” the magnificently moody, sumptuously gifted Bulgarian once said and what’s the betting his nation’s football federation weren’t aware of the quote when they unwisely installed him as Bulgaria’s head coach in 2004?

A failure to qualify for the next World Cup followed, as well as inevitably a soap opera’s worth of strife. Two of his captains quit, insisting they could not work with Stoichkov, in three turbulent years.

And so to Celta Vigo, where he promptly got them relegated. By the time of his sacking Os Celestes were dangerously close to plummeting into the third tier.

A truly elite player. A terrible coach.  

Thierry Henry 

Respected for his punditry, admired for his work as Belgium’s assistant coach, and hugely lauded for the weekly miracles he performed as a player, Henry got the managerial itch in 2018, when Monaco dismissed Leonardo Jardim. 

Returning to the club where he first made his name, Henry said the right things, and no doubt improved his star-struck players in training, but on the pitch Monaco’s fortunes slumped alarmingly, taking them into the clutches of a relegation dogfight. 

With defeats racking up in a regular basis, the Arsenal legend was fired with just under half the season still to play.


*Credit for all of the photos in this article belongs to Alamy*

Stephen Tudor is a freelance football writer and sports enthusiast who only knows slightly less about the beautiful game than you do.

A contributor to FourFourTwo and Forbes, he is a Manchester City fan who was taken to Maine Road as a child because his grandad predicted they would one day be good.