Richardson gravitated towards parks, analysing and digesting games with a modicum of seriousness.
"It was my dream from that early age to play for the West Indies."
He did, going on to become a captain, succeeding Richards late in 1991.
Roberts and Richards were the only two players from the smaller islands of Antigua to have represented their country before Richardson.
"When they played, they gave me hope. I thought, 'Great, they've done it, they are pioneers and they are poor boys so I'm going to do it as well'."
Under his captaincy, Curtly Ambrose and Courtney Walsh led the bowling attack and a world-class Brian Lara was in the making.
By nature, Richardson was a competitive beast, no matter what code.
If it was football, he trained to be the best and put up challenges to make incremental gains, such as play in every position.
"If I was weak in a position then I used to deliberately put myself in that position to become stronger."
In cricket, he diligently toiled to become adept in devouring express deliveries but spin bowling left some room for improvement.
"Towards the end of my career, to me, I was a better player of spin than fast bowling," says Richardson, who began his career with the Leewards Islands in 1982 as an opener.
His act of premeditated defiance extended to taking on the world's best. If someone was touted as the fastest bowler then Richardson wanted to face him.
"If he was the best spin bowler then I wanted to take him on because it's not about who's easy but who's tough."
Pakistan leg spinner Abdul Qadir Khan, Sir Richard Hadlee, of New Zealand, Kapil Dev, of India, Imran Khan, of Pakistan, and dreaded bowling compatriots Wasim Akram and Waqar Younis were among bowlers he saw as yardstick of batting excellence.
"So I like challenges and that's what life should be all about.
"I always aspired to be great but at the same time I also wanted to remain humble."
Richardson played 86 test matches until 1995, scoring 5949 runs and 16 centuries. He relished playing against Australia, carving up nine tons against them.
His highest score of 194 was against India in Guyana in 1989. He also played 224 ODIs, including three World Cups.
When the dust settled after series and cups, he savoured the camaraderie and to this day maintains ties with some of the players.
His upbringing was modest, with his parents "working hard and they struggled".
"You know, many times we didn't know where our next meal was going to come from but a lot of us from the village were like that."
Growing up, Richardson got his hands dirty planting vegetables and went spear fishing to make ends meet in a typical subsistence economy environment.
Living in nearby Cedar Valley, St John's, these days, Richardson is looking forward to returning to his roots when he's retired.
From time to time, he visits the village where his brother and sister still live.
Richardson knew he was going to represent his country when he played his maiden first-class game for Leeward Island against Barbados as an 18-year-old.
His time at the New Zealand and Australia co-hosted ICC World Cup will leave indelible impressions on his mind.
"Especially in New Zealand, where we've been very well looked after," he says, overwhelmed with the service at the Te Pania hotel.
The role of team manager isn't a dream come true because he's always regarded himself as a servant of West Indies cricket in every conceivable manner.
It didn't cross his mind at the end of a rewarding playing career although he did contemplate coaching at a grassroots level.
"I really believe that's [grassroots] where it can make a big difference."
However, when approached to assume the mantle of team manager, Richardson couldn't turn it down.
"There's been some changes and it's been a new experience for me but I've learned a hell of a lot. It's something I've enjoyed and I'm glad I've accepted the opportunity."
The role now is total contrast to playing and somewhat of an eye-opener.
"I have to admit, as a player, it was a lot easier, much easier," he says, throwing his head back in laughter from the comfort of the lounge suite at the foyer of the hotel.
No stranger to working hard, Richardson has no qualms about the role but it's a lot harder than the playing days when they trained and studied the strategies to go into battle.
Before jumping on board with the Windies, he was running a sports tourism business in Antigua that entailed similar skills.
"When I'm finished, done with this, I'll be in a fairly good position to take good care of my business."
Having fulfilled his role as a Windies captain, it isn't surprising that the incumbent crop of players look to him for support and guidance.
"I also get a lot of respect from the players."
With the contrast of two teams - test and ODI - he embraces different challenges in his managerial role.
"The characters in the ODI team seem to be more outgoing and have bigger names such as Chris Gayle and, in T20s, Kieron Pollard, although he's not here."
Ditto Dwayne Bravo who also isn't in the World Cup equation.
"You know, you have to make adjustments when you have ODI players and test players ... but they are a good bunch of guys generally."
No doubt he comes across the "odd problem here and there" but, generally, they are workable and responsive.
He still harbours a desire to nurture youngsters once his tenure is over.
"Other than that, I just want to retire and be happy with my family in Antigua, play some golf and have a quiet life."
Richardson's prowess isn't limited to the pitch. Since 2001, he reportedly played a bass guitar in a reggae band, Big Bad Dread and The Baldhead, alongside Ambrose, who is the bowling consultant in the current squad.
Richardson was knighted in February last year.
