The first of a three-match contest starts at Birmingham's Edgbaston ground today with the inaugural day/night Test in England.
West Indies have not won a Test in England since 2000, just part of a miserable overall away record during the last 20 years.
They have also arrived without several star players, the legacy of a bitter dispute with administrators and a clash with the lucrative Caribbean Premier League Twenty20 tournament.
England come into the series fresh from a 3-1 home Test success against South Africa.
"Over the years, it's always amazed me with England," Richards told Thursday's edition of The Times.
"They never win as much as they should," he added at an event staged by the Lord's Taverners cricket charity.
"I look at the Champions Trophy -- there was no better team for that format but they still fell short.
"England have the right stuff in their teams but then they fall down at some hurdle or just don't jump high enough."
Known for his intimidating presence at the crease, Richards urged Jason Holder's side not to be overawed by England.
"I hope the West Indies team can see that England are beatable," said Richards, who also enjoyed success in English county cricket with both Somerset and Glamorgan.
- 'Hurt' -
==========
As such, watching their decline has been particularly painful for the 65-year-old Antiguan
"It does hurt that the glory days have been lost," he said.
"I was doing some television work during the Champions Trophy and there was no West Indies there. No West Indies. That's like saying there would be no Chelsea or Arsenal in the Premier League. That's how it felt."
"Yes, we had our differences (when I was playing) but what stood us out was when we put on that maroon cap there was a real sense of pride. I want to see that return, I want to see that in this group.
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