Riches to rags: Players who lost it all
He reportedly earned in excess of £20 million (S$35.6m) during his time in the Premier League.
James even held an online auction to sell off some personal belongings and football memorabilia
But an expensive divorce in 2005 led to a build-up of debts that he struggled to pay off and in May 2014, James eventually declared himself bankrupt.
In November that year, he even held an online auction to sell off some personal belongings and football memorabilia.
Hendrie made his debut for Aston Villa's senior team at the age of 18 in 1996, spending the next 14 years at Villa Park.
At the peak of his career, Hendrie was earning a reported £40,000 a week.
He went on to play for a number of other clubs including Stoke City, Leicester City, Blackpool and Brighton and Hove Albion, before signing for Indonesian outfit Bandung FC.
But in January 2012, he was declared bankrupt by Her Majesty’s Revenue and Customs at the High Court.
It was reportedly due to some failed property ventures, where he lost approximately £10 million and was £1 million in debt.
A lavish lifestyle and a divorce along the way added to his misery, as he attempted to commit suicide twice. But he has since been rebuilding his life, including getting involved in children's football schools.