But earlier this month, India's Supreme Court said the company's phone unit had disobeyed a ruling to hand over payments totalling around US$77 million to the local subsidiary of supplier Ericsson.
If the company fails to cough up within a four-week deadline, Anil could spend three months behind bars.
Reliance Group has also taken hit after hit as a result of financial losses and increased competition within the telecommunications industry.
"Telecom was a tale of disaster for Anil owing to cutthroat competition, which led to industry-wide consolidation and debt overhang," Ascentius Insights principal analyst Alok Shende told Bloomberg.
Mukesh was prevented from moving into telecommunications by a non-compete clause — but when it ended in 2010, he muscled in and built Reliance Jio Infocomm Ltd, which launched a 4G wireless network across India.
As competition stepped up, Reliance Communications borrowed more and more.
But it wasn't enough to stop the company from dropping out of the number two position on the market.
Meanwhile, other branches of the company also started to falter, with shares falling in warship maker Reliance Naval & Engineering Ltd and power generator Reliance Power Ltd.
Today, Forbes estimates Anil's net worth to be just US$1.7b, representing a stunning US$40b loss over just one decade.
But while Anil is facing an uncertain future, his brother and fierce rival Mukesh is going from strength to strength.
Last year, Forbes named him as India's richest man with a net worth of US$47.3b.