The Toughest Gigs in Football Management

It takes a special kind of guy, or a glutton for punishment, to manage a football team but some jobs seem damn near impossible.  There may be harder ones out there, but here I’m going to run through a few of the toughest.

Real Madrid

The Real Madrid manager’s job comes with a huge weight of expectation. With Barcelona as strong and talented as they currently are; winning the required amount of silverware simply isn’t realistic but nevertheless it is still expected – and demanded.  Carlo Ancelotti was probably their best boss in recent years and even he didn’t make the grade as Real showed little loyalty despite his La Decima success.

Then there’s the rumours of player power/unrest, an over-involved board and the supporters, who want entertainment as well as results. It all adds up to almost certain failure.  Rafael Benitez is the man in the hot seat right now and he got what looks like a stay of execution earlier in the week, but I’d be amazed if he lasts the season at the Bernabeu.


Sunderland have a big stadium, passionate fans and seemingly enough money to build a competitive Premier League team – but no one has managed to put all the pieces together.

Established names like Martin O’Neill and Dick Advocaat (although he was never seen as a long-term option) have failed to build anything substantial at the Stadium of Light and up-and-comers like Gus Poyet and Paolo Di Canio also haven’t worked out.

I never really thought much of Di Canio, that seemed a weird appointment, but Poyet arrived with a bit of promise and didn’t fare much better.  I don’t know exactly what the problems at Sunderland are, I’m not sure anyone does (plenty have offered their theories over recent years, Niall Quinn talked of ‘Gremlins’, Poyet said he knew there was ‘something wrong’ but never managed to pinpoint what that was, those thoughts were echoed ominously by Advocaat prior to his exit earlier this year…), but I do know Sam Allardyce has a huge job on his hands.  If anyone can help them avoid the drop and build something he’s the man, he did it at Bolton and West Ham, but even this may be beyond Big Sam.

Bolton Wanderers

What Allardyce built others have since demolished, leaving current Bolton boss Neil Lennon without a pot to piss in, probably literally.  The problems with Real and Sunderland are more long-term but what Lennon has now is arguably the toughest gig in football management.  He’s got no money for players and not only that – the club decided not to tell him the funds had dried up until around the time a loan move for a winger who can’t get in the Wolves team fell through.

The saving grace for Lennon is that the fans, largely, seem to understand.  The Wanderers faithful got some unfair criticism from various pundits and the press in general when Gary Megson left, when anyone who really saw what was going on there knew he was out of his depth.  The Leicester fans were ecstatic when he departed and the Sheffield Wednesday fans were disappointed when he arrived, which says a lot about his abilities – or lack thereof – as a manager.  If Bolton can get a new owner in Lennon’s job, theoretically, becomes a lot easier (unless the new man makes an immediate change, which isn’t beyond the realms of possibility) but at the moment he probably feels like he’s trying to climb a greased up ladder with his arms tied behind his back.  He might get so far – but sooner or later he’s going to slip back down again, cracking his face, his nuts or both on each rung on the way to the ground.


Maurizio Zamparini bought Palermo in 2002 and since then they’ve gone through managers like I go through questionable metaphors. At my count they’ve had 28 in 13 years, which makes Sunderland look stable.  Delio Rossi was fired, hired and fired (resigned by ‘mutual consent’ technically) again within the space of five months and his replacement, current Lazio boss Stefano Pioli, lasted just 90 days.  I’m a huge fan of Zamparini – if you don’t know about him or want to know more, take a look at this – but I wouldn’t want to work for the guy.

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