He used a mobile phone from Tihar jail and swindled people pretending to be either a government officer or a minister's aide or even a Supreme Court judge. She collected the money outside through hawala channels.
They built a fortune and flaunted a sea-facing bungalow in Chennai, a fleet of cars and a wildly extravagant lifestyle.
Conman Sukesh Chandrasekar's latest swindle was exposed when investigators questioned two actors.
One of them is Sukesh Chandrasekar's alleged partner-in-crime Leena Maria Paul, a small-time actor who starred in the 2013 film Madras Cafe. The other is Jaqueline Fernandes, a friend of Leena Maria Paul and allegedly one of the couple's victims.
According to sources in the CBI, Enforcement Directorate and Delhi Police, there are over 23 cheating cases against Chandrasekar and Leena Paul across the country.
The Chennai bungalow was bought with Rs 200 crore that the couple allegedly scored off their latest victims - the wives of former Fortis Healthcare promoters Malvinder Singh and Shivinder Singh. The police say Chandrasekar and Leena pretended to be close to the Home Minister and Law Minister and promised to help their husbands secure bail. NDTV reached out to Malvinder Singh and Shivinder Singh's families but received no response. A copy of the FIR filed by Aditi Singh, Shivinder's wife, confirms the charge.
The bungalow, filled with lavish furnishings, also featured a racing car in the living room - a Mercedes Benz 300 SLR with 722 emblazoned on it, apparently from the famous Mille Miglia race of 1955.
The Enforcement Directorate has seized goods worth Rs 20 crore till now, including shoes, bags and clothes from brands like Ferragamo, Chanel, Dior, Louis Vuitton, Hermes and Versace. The couple owned a Rolls Royce Ghost, a Bentley Bentayga, a Ferrari 456 Italia, one Lamborghini Urus, an Escalade, and a Mercedes AMG 63.
In jail since 2017, Chandrasekar continued conning businessmen and politicians off over Rs 100 crore. He allegedly used high-end devices for his cons. Agencies suspect the money was routed through Leena's family in Dubai.
Chandrasekar was 17 when he was first arrested, in 2005. He allegedly cheated a Bengaluru-based couple of Rs 1.14 crore after pretending to be a friend of former Karnataka Chief Minister HD Kumaraswamy's son.
In 2013, he and Leena Maria Paul were arrested for fraud worth Rs 19 crore in Chennai involving Canara Bank.
He was charged by the CBI last year for allegedly posing as the agency's director and extorting money from TDP MP Sambasiva Rao, who is an accused in a Rs 6,000 crore bank fraud case.
While investigating this, the CBI learnt that Chandrasekar had swindled former AIADMK chief VK Sasikara's family after pretending to be a Supreme Court judge who would ensure her early release from a Bengaluru prison.
While the Enforcement Directorate is tasked with recovering the money that runs into hundreds of crores, the Delhi Police is working on a water tight case to secure a conviction -- the first in 16 years.
Sources said the CBI has written to Delhi Police on the phones seized from Chandrasekar in jail to try and decipher the technology he used; he always managed to have the number of a senior government functionary on his phone display while deceiving people.