It was a sad decline, West Indies legends retired and they were never truly replaced. They managed through the 90s with Ambrose, Walsh, Lara and Chanderpaul in the side, but when England beat West Indies in 2000 for the first time in a VERY long time that was it. Even with Walsh and Ambrose bowling at them England managed to pick off the other bowlers and then the West Indies dramatically collapsed when England for a rare occurence themselves played Cork, Gough AND Caddick in the same side and took the West Indies apart. Once Ambrose and Walsh retired that was more or less it, Lara, Chanderpaul and some others. To be fair one or two bowlers have come through and looked nearly men, but the batting is too fragile and there's not enough bowling to carry them very far.
The problem won't be helped by the side being so poor, watching your team get thumped is hardly a way to excite youngsters into wanting to take up the sport. Maybe the West Indies should move away from USA, that might help!

Once the likes of Greenidge, Haynes, Marshall, Richards and Dujon retired the side became at best average and continued to slide. England did very well to draw the 1991 series, for me a better performance than the 2000 series win against a much weaker West Indies. I reckon maybe even the win that should have been out in West Indies around 1989/1990 was a better England performance, robbed only by cheating tactics of bowling 11 overs an hour so England didn't reach their target

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Needing 151 to win, with virtually all day in which to get them, England were given a positive launch, 25 coming from six overs. Larkins then fell to Moseley, who struck a more grievous blow by banishing Gooch in agony. The extent of his injury was kept from the England players while they fretted through the rain-ruined afternoon. When play resumed, in barely fit conditions, 78 were required from 30 overs, of which only seventeen were bowled before the light became too dangerous. England had lost wickets at vital times and, just fleetingly, a West Indies win had seemed possible. With delaying tactics of a blatant nature dictating the pace of the play, it was an unsatisfactory finish to an otherwise marvellous match.
Wisden - WEST INDIES v ENGLAND 1989-90
Crucial point in the series, 1-0 up at the time of this 3rd Test with the chance to go dormie 2-0 up with two to play, England denied by weather and cheating. Sure England might have tried the same, but I doubt they could have managed to waste as much time and as many balls/overs. Fortunately not too many games finish so close to the wire, these days it seems to be the batting side wanting to waste time more than the fielding side and it's easier to waste time when bowling, there are certainly more tricks like intricate field setting, tying bootlaces, changing your mind over who bowls, aborting run-ups, bouncing excessively, bowling as wide as is legal, bodyline etc. Batsmen can waste time, but not quite as often without being obvious during an over.