I think this from the Observer 2005 sums it up quite well. Great players often don't make great managers especialy at clubs like ours. We've had arguably 2 of the best English players in David Jack and Bobby Moore managing us and both in terms of results were "failures".
"History will always consider Moore a managerial failure, and his record at Southend was unimpressive: relegated to the Fourth Division in his first season, barely staving off the humiliation of having to seek re-election to the Football League in his second, mid-table anonymity in his final year. But backroom disruption always left him facing an impossible job. When Moore joined, Southend had just been taken over by the Essex builder Anton Johnson, who had ambitions to turn it into a grand sporting club. Inviting a rugby league team, the Maidstone-based Kent Invicta, to share the Roots Hall stadium was one of his wheezes. But Johnson was short of both money and fans. Debts rose to £700,000 and even the fans' Christmas loan fund was purged of £70,000. At this point, the Serious Fraud Squad was called in. In December 1985, the Football League banned Johnson from any further involvement in football and he was later declared bankrupt with hundreds of thousands owed to creditors.Moore's role in all this remains sketchy. His position as chief executive was seemingly titular under Johnson, as he was never implicated in any of the police or FA investigations; he went on to serve Vic Jobson, Johnson's successor as chairman. Indeed Moore, as much as anyone, could be credited with saving Southend. Not only was he left to unravel the mess left by Johnson, but he also stepped in as manager following the sacking of Peter Morris in February 1984. As if by accident his break into management had finally come.
'It must have been very stressful for Bobby working there,' says Stephanie Moore. 'They didn't know how they were going to pay the players. They'd get to the end of the week and somebody would say, "Oh, we've got a game tomorrow". Bobby was involved in all this other stuff , the last thing he was allowed to do was really pay much attention to the team. He was too busy trying to keep the club afloat.'
By the summer of 1985, Jobson was in full control of the club and, for the first time since Moore's arrival, there was some stability. Frank Lampard, another former West Ham player and the father of the current Chelsea star, became player-coach and there was money to sign new players. Lampard describes Moore as 'an excellent, excellent manager for the players', who never really lost his temper. If he did throw a tantrum, 'it didn't really look like him, it didn't have that same effect'.
Moore's grace on the football field had once exuded a natural authority, says Lampard - an 'aura', something you couldn't quite put your finger on. Instructing lesser players wasn't so easy. 'He would often talk about great players not making good managers because they played through instinct,' says Pearce. 'I don't think Bobby was ever going to be a football manager. He wasn't a success when he dabbled in it because he was a player of such great ability. I'm not sure he was able to coach players of poor ability and make them great players - or even better players.'
Moore's time at Southend ended with further backroom arguments. Jobson had already objected to Moore moving back to live in central London so that Stephanie would be closer to her workplace. Then they fell out over team selection. 'There were one or two players,' recalls Lampard, 'and Vic wanted them to play, but they weren't in the starting line-up. Bob was very hesitant about what to do about it. Once that happened, that was the end of me being there. I can't even remember whether Bob changed the team, but it left such a bad taste. Two weeks later, Bob left too. And that was it.'
When Moore left Southend in April 1986, it was effectively the end of his managerial ambitions. A couple of months later, he had a new job: as sports editor of Britain's newest tabloid, the Sunday Sport, a product of the technology-led expansion of press titles. Its owner, David Sullivan, had made his fortune from pornographic magazines"
