"If [James] had a new car and he pranged it, he would just go and buy a new car - so there were five cars parked in the drive. If he bought a new pair of shoes and he scuffed them, he wouldn't clean them. He would just chuck them in the spare room and buy a new pair. Too much disposable income, I suppose. Too easy just to bin stuff." But there's also another side to James, an affable footballer who was always one of the free spirits in an England era when the biggest players often found themselves dictated to by overbearing agents.
He earned his last cap in the defeat to Germany at the 2010 World Cup, one month short of his 40th birthday, having lost and won back the No1 jersey more times than he cared to remember.
James is in India because, friends say, he wanted to manage a team and, given a nice life as a BT Sport pundit, it was hardly the easy option. Kerala are seventh in an eight-team league and, once the competition finishes on December 9, his contract will be up.
Despite his status as a player, it has not been easy to find coaching work and James hopes to get his Uefa A licence with a view to a career in management. Informed sources say his salary peaked at 50,000 a week probably at Portsmouth during their ruinous spending spree under owner Sacha Gaydamak.
James was generous with his money and established his own foundation to sponsor projects in Malawi and is understood to have directed much of his personal earnings towards its work. His long-running column in The Observer newspaper was done in return for a charitable payment.
Those who knew James would never pretend he was good at managing money but none would claim he was ever greedy.
The details of his decline into bankruptcy are sketchy but his divorce from first wife Tanya was significant and there were other failed investments.
His career earnings are estimated at 20 million, gross.
Those who know him say he has taken his bankruptcy with the philosophical approach he has tackled the ups and downs that have characterised his career. UK Telegraph
