On July 19, when news of businessman Raj Kundra’s arrest by the Mumbai Crime Branch in connection with a pornography racket started trending online, no one was really surprised. After all, this was not Kundra’s first brush with the law.

A college drop-out, the South London-born Kundra moved to India only after he married actor Shilpa Shetty in 2009. The couple met during her successful stint on Celebrity Big Brother in the UK. Kundra started by handling her perfume business and the production of Miss Bollywood, a stage extravaganza she starred in, for which he travelled with her through Europe in 2007. While being a part of a high-profile relationship brought him to a new country and opened new doors for Kundra, it also meant that there was more scrutiny into all aspects of his life, starting with his businesses.

In the early years of their relationship, Shetty often described him as an entrepreneur and one of the richest Indians in the UK, while Kundra rarely spoke publicly and little to nothing was known about his businesses. There were some vague mentions of companies that traded in diamonds and import-export, but the couple maintained that producing Bollywood films was where their future lay. That plan didn’t really materialise, though.

Their first big financial investment as a couple was as co-owners of Indian Premier League (IPL) franchise Rajasthan Royals in 2009. Player auctions, private jets to view matches and post-match parties — the couple quickly became an integral part of the IPL juggernaut. As he grew more comfortable under the spotlight, Kundra began to branch out. He wrote a novel, “based on a real story”, titled How Not To Make Money that was published by Random House. And, launched a series of unrelated, but celebrity-led businesses. He also ventured into the home shopping space with Best Deal TV along with Akshay Kumar in 2015. He replicated the ‘league format’ with other sports and launched Super Fight League, an MMA-style tournament in partnership with Sanjay Dutt in 2012. This was followed by the Match Indian Poker League, a regulated poker tournament, launched in 2017. All three of these businesses have either faded away or lie dormant today.

It was the most visible of all his ventures where Kundra first ran afoul with the law. When the infamous IPL betting scandal broke in 2013, his was one of the big names that came up in the probe with the then ICC chief N Srinivasan’s son-in-law Gurunath Meiyappan and Rajasthan Royals cricketers S Sreesanth, Ajit Chandila and Ankeet Chavan. The police stated that Kundra would place bets via the team co-owner Umesh Goenka. As a result, Kundra was suspended from all cricket-related activities for life and RR was also banned for two years. In 2018, however, he was given a clean chit by the Delhi police.

Kundra has been in troubled waters quite regularly in the years since. In 2018, he was questioned by the Enforcement Directorate in connection to a crypto-currency scam to the tune of Rs 2,000 crore. In 2019, he was questioned by the Enforcement Directorate in Mumbai during an investigation in the Prevention of Money Laundering case against Dawood Ibrahim’s aide and late drug trafficker Iqbal Mirchi.

Last year, as the pandemic hit the world, the couple welcomed their second child Samisha, who was born via surrogacy. Kundra entertained his 700k followers on Instagram with videos where he morphs into Ranveer Singh, Iron Man and Lionel Messi and even does the occasional pati-patni comedy video. On the surface, things could not have looked any happier for the Shetty-Kundras, but the multiple legal issues they were facing had begun to catch up.

There was a police complaint of cheating and fraud concerning Satyug Gold Pvt Ltd, a gold trading company, where they are ex-directors. They were also summoned by the Ballard Pier magistrate’s court for delay in the payment of tax deducted at source (TDS) by Best Deal TV.

Significantly, the investigation by Maharashtra Cyber Cell for obscene content also started last year culminating in raids on a Madh Island bungalow in February where two women were found in a state of undress. And this is where Kundra seems to have dug himself deeper than he had ever done before. In 2019, he invested in the tech start-up Armsprime Media that built and monetised celebrity apps. Among Armsprime Media’s clients were models Poonam Pandey, Sherlyn Chopra and Gehana Vasisth.

Among those arrested in February was Rowa Khan alias Yasmeen, who claimed to be a producer-director. The police later learnt that Khan runs a mobile app called HotHit Movies, where porn videos are uploaded. Interestingly, Armsprime is the company that developed and monetised apps like HotHit Movies and HotShots. Mumbai police have said that Kundra’s name came up during the investigations in connection to his links to the company that hosted pornographic films on digital platforms.

There is a related case where the Maharashtra Cyber Cell had issued an FIR against 14 web portals and streaming services for obscene content in 2020. One of the apps belonged to Armsprime Media for which Chopra shot a film titled Chocolate in December 2019. In her statement to the Bombay High Court in April 2021, Chopra said she was told to “let go of my inhibitions and open up like Hollywood models”. It was Chopra who mentioned Kundra’s involvement in the company in her statement. When summoned by the cyber cell, the businessman maintained that he had exited the company in 2020, though he did apply for anticipatory bail in June 2021.

In a 2013 interview to Business Standard, Kundra talks about how he learnt the value of money from his father Bal Krishan, who started out as a cotton factory worker and bus conductor in London and went on to build a grocery business and buy post offices. Sent off by his father with 2000 pounds on his credit card to make something of himself, he claims he made millions in his first venture — selling pashmina shawls. In recent years, references to his rags-to-riches journey often come up in his #rajmantras Instagram account. In one post he wrote, “When you have made it from scratch nothing can stop you ever! Money might not buy happiness but it gives you the freedom, opportunities and options. Never give up! (sic)”. As the 45-year-old spends the next few days in police custody, he might want to think about that other famous quote by Ralph Waldo Emerson — “Money often costs too much”.