Prior to 1995, the West Indies' cricket team had not lost a Test series (home or away) against all opposition for 15 years. Between 1995 and 2008, the West Indies has not won an away series, save against lowly Bangladesh and Zimbabwe. If this is not enough evidence of the West Indies' decline- the West Indies has tumbled from being the unofficial number one team in the cricket world to the nether regions of the official ICC Test and ODI table.
A former South African cricket and a West Indian commentator were discussing possible reasons for the West Indies' decline. The apartheid-conditioned, white South African suggested that the West Indies were the best side for 15 years because the other sides were poor. He suggested that when the other sides became good, the West Indies team performance declined. This intellectually-challenged perspective does not consider the reality of West Indian society.
The 1995 West Indies team that lost to Australia was far from the world-beaters who regularly trounced teams like Australia and England at home. Teams were literally terrified of playing the West Indies, who had a lethal bowling attack and world-class batsmen in their ranks. However, for more than a decade, the West Indies has struggled. Many reasons have been forwarded for this.
Poor player development
The players on the world-beating West Indies teams had the attitude and opportunities to hone their skills. They were involved in the English County championships and the Kerry Packer World Series. This afforded the legends of that team the opportunity to develop a professional attitude to the game. The modern West Indian player does not have much support or development facilities in the Caribbean after all these years.
Low quality and quantity of cricket matches
The West Indies' First-class season (the level below Test cricket in the region) is a joke. Teams are normally scheduled to play 5, 6 or 7 First-class games in one year. Also there's a one-day championship in which very few games are played. In other countries, teams play much more than 12 cricket games per season. Many West Indian players do not have the opportunity to play much cricket outside of international cricket, especially since the English Cricket Board limited overseas players in the English counties.
Poor attitudes
The current bunch of West Indies players fail to respect the West Indian legacy in cricket and appear to have a poor work ethic. Their approach to fitness is non-existent and their lack of application is often embarrassingly highlighted on the field of play. The poor attitude has often led to disputes between players and team management, the board and intra-team conflict.
Administrative bungling
The West Indies Cricket Boards is in financial debt and organisational disarray. The poor cricket administration extends to tour preparation as well. The WICB does not seem to have a vision for West Indies cricket. It also seems to create conflict or confusion (Digicel vs Bmobile & Stanford vs Digicel, for example) that is harmful to the development of cricket in the region.
The losing mentality
Winning is a habit. Losing can become a habit as well. The West Indies are so accustomed to losing that they even managed to lose games from strong positions. Lack of confidence and the inability to capitalise on winning positions have plagued the team, especially on overseas tours (recent example: 2006 Test series against New Zealand).
ICC Future Tours Program
Previously, the West Indies would make a profit from going away to countries like England and Australia. With the ICC Future Tours program, the West Indies does not receive revenue from its overseas tours. Apart from this, an impoverished WICB is forced to host matches against countries that cannot be marketed to West Indies cricket fans effectively.
When New Zealand, Zimbabwe and Bangladesh tour the Caribbean, the WICB never makes a profit. The ICC's stance on the issue is partially aiding the West Indies' decline, while it seeks to expand the game. This is ironic since the West Indies is the only part of the Western hemisphere that cricket is taken seriously.
Conclusion
There may be several other reasons for the continual failure of the West Indies on and off the field of play. While most teams face periods of drought as part of the sports cycle, the West Indies has been in the doldrums for far too long.
The Stanford 20/20 competition is welcome in the Caribbean as it injects much-needed cash and resources into the game. More importantly, it has revived interest in cricket around the region. Stanford claims that his input will turn the West Indies' fortunes around. Whether his input can offset the many factors responsible for the West Indies' decline is left to be seen.