In 2011, Roy teamed up with liquor baron Vijay Mallya of Kingfisher beer fame, paying $100 million for 42.5% of his Force India Formula One auto racing team.
It paid $370 million for a franchise in cricket's Indian Premier League.
In 2010, Sahara considered buying English Premier League soccer club Liverpool and held talks to buy the debt of film studio Metro-Goldwyn-Mayer.
Neither deal happened.
Still, Roy is not typically bracketed with a corporate elite led by Indian families such as the Tatas, Birlas and Ambanis.
"If you look at the orthodox business community, they have kept him at arm's length," said Ashok Prasad, a physician, lawyer and academic who taught overseas before returning to Gorakhpur, the city where Roy started out.
Instead, Roy is associated with Bollywood celebrities and, like many tycoons, is seen as having good political connections.
Last year, KM Abraham, then a SEBI board member, which had ordered that the bonds be refunded in the case that ultimately went to the Supreme Court, wrote to the prime minister alleging "undue pressure" from the then-finance minister and his office to deal leniently with high-profile cases, including Sahara's.
The Finance Ministry and the regulator denied the allegations.
Image: Bollywood star Kareena Kapoor (centre, in black) dances at the Sahara Indian Sports Awards in Mumbai on October 31, 2010.