Trouble was, we were ready, willing but ultimately unable. Then, 20 years later, with an emaciated ground, embarrassing home support and a volatile boardroom / fan relationship, along comes the big time, just when we're least expecting it.
That's when you find out what kind of club you support. In the lower echelons it's easy to dream of being another Watford, an Ipswich maybe - or even a Norwich. Then the First Division doors creak open, the light shines in, and you realise you're an Oxford United, perhaps a Grimsby, or - pass the dark glasses - maybe even a Shrewsbury Town.
Such unpalatable truths have been pushed to the back of the mind in the exciting three years since Southend emerged from the Third Division for the first time in their 87-year history. The good times under David Webb and Barry Fry have kept attention away from the poor crowds and backroom intrigue, but Fry's traumatic departure has ushered in a new, unwelcome era of soul-searching.
What is more, the chances of Roots Hall transmogrifying from its dilapidated state remain gloomy and the horrible spectre of a move to Basildon refuses to go away.
On the field, there are other horrible spectres (Andy Sussex for a start), and with the regular departure of top-line players like Stan Collymore, Brett Angell, Dean Austin and Peter Butler, the resources are thinning by the day.
In fact, the only bright spot on the pitch at the moment is Ricky Otto, who burgles his way through defences and is already attracting Premiership interest. Barring complete collapse, Southend are safe from relegation this season, but when Otto is snapped up by one of those big-fish predators maybe it will be time to start thinking about a return to the Second Division.
The truth is that Southend have already blown their best chance of becoming a small-time, big-time club. The players and the managers have done their bit, but the fans and the facilities are unreadier than Ethelred. For now the best philosophy is to have First Division fun while the tide is in, because when the tide goes out at Southend, all you have left is mud - and lots of it.
Peter Mason is author of Southend United: The Official History of the Blues.Reuse content