Chhota Shakeel gang

The Chhota Shakeel gang, also known simply as the Shakeel gang, stands as one of the most powerful and feared criminal organizations in Mumbai's underworld. As a faction of the sprawling D-Company network, the gang has been defined by its ruthless violence, its transnational reach, and, most strikingly, its incorporation of women into positions of real operational authority. The gang's story is inseparable from the broader history of Mumbai's mafia, yet its particular significance lies in how it functioned as a structure within which women like Rubina Siraj Sayyed could rise from obscurity to become powerful, notorious figures, managing finances, coordinating with lawyers, and overseeing the welfare of jailed gangsters. The gang's operations, spanning extortion, drug trafficking, and political manipulation, reveal the deep entanglement of crime with the legitimate economies of the city, and its history offers a lens into the gendered dynamics of the underworld that the book's narrative seeks to illuminate.

Origins and Place in the Mumbai Underworld

The Chhota Shakeel gang emerged from the turbulent landscape of Mumbai's criminal underworld, a world shaped by the earlier generation of gangsters who established the city's major criminal networks. The gang's lineage can be traced to the formidable alliances of the mid-twentieth century, when figures like Haji Mastan, Karim Lala, and Vardharajan Mudaliar formed some of the most powerful gangs in Mumbai. Mastan, who had arrived in Mumbai in 1934 and risen from a cycle mechanic to a dock coolie in 1944, amassed millions through smuggling gold, silver ingots, and electronic goods, and his villa, his Mercedes, and his tremendous influence were all offshoots of his illegally hoarded wealth. This earlier generation of gangsters, operating in an era of prohibition and smuggling, laid the groundwork for the more organized and violent gangs that followed, including the D-Company and its constituent factions like the Chhota Shakeel gang. The gang's rise was part of a larger shift in the Mumbai underworld, where the old guard of smugglers gave way to a new breed of gangsters who combined extortion, contract killing, and drug trafficking with the political and communal tensions that would come to define the city in the late twentieth century.

Rubina Siraj Sayyed and the Gang's Female Operatives

The Chhota Shakeel gang's most distinctive feature, as documented in the book, is the prominent role played by women in its operations, a fact that sets it apart from many of its rival gangs. Rubina Siraj Sayyed's trajectory into the gang illustrates this dynamic. A beautician in south Mumbai's Dongri area, Rubina was much in demand for her expensive beauty treatments at social events and weddings, earning an annual income far higher than that of her civil contractor husband, Siraj Sayyed. Despite her success, she was not satisfied, harboring bigger dreams of joining politics and becoming a municipal corporator. Her entry into the underworld began in 2002 when her brother-in-law, Obaid Sayyed, a Shakeel aide, was arrested in a murder case and lodged in the Arthur Road Jail. During her visits to the court and jail, Obaid asked her to convey messages to Shakeel, and she agreed. A smooth talker with a flirtatious voice, Rubina managed to flatter the fugitive gangster, and an impressed Shakeel asked her to join the gang, an offer too lucrative for her to refuse. She assumed that her role in the underworld would boost her chances of contesting the municipal elections, and she started working for the gang almost immediately, taking instructions from Shakeel aide Fahim Mach-Mach, coordinating with lawyers, handling the financial affairs of all gang members between south Mumbai and Jogeshwari, and looking after all the needs of Shakeel's gangsters in jail. In only a few months, her lifestyle changed tremendously; she moved from riding a two-wheeler to driving a car, and from being a beautician, she became the notorious, powerful 'heroine' of an underworld gang. Rubina's fluency in English and tech-savvy nature allowed her to evade the police's electronic surveillance time and again, and the Crime Branch only discovered her activities a year later, after one of Shakeel's men, Uday Pawar alias Pankaj, got in touch with her.

Operations, Extortion, and the Mechanics of Power

The gang's operational methods, as revealed through Rubina's activities, demonstrate a sophisticated blend of violence, financial management, and legal maneuvering. For a couple of years, Pankaj had been demanding Rs 50 lakh from a film distributor and issuing threats to him. When the distributor agreed to pay Rs 10 lakh, Pankaj called Rubina to report this to her, and the police, who happened to be listening in on the conversation, began tracking her movements and calls, recording twenty-six conversations made to Fahim Mach-Mach and Shakeel. After watching her closely for over four months, the Crime Branch finally arrested her in 2004. According to the police, at the last count, she was looking after twenty-five families of men affiliated to the Shakeel gang and would distribute Rs 1.5 lakh among them every month, apart from making payments for legal expenses. This role as a financial manager and jail liaison was crucial to the gang's cohesion, ensuring that the families of incarcerated members were supported and that legal defenses were funded. The gang's reach extended beyond simple extortion into the broader criminal economy of Mumbai, which included drug trafficking networks and the smuggling routes that connected the city to the Gulf and Nepal. The gang's power was also felt in the real estate sector, where, as seen in the activities of other underworld figures, builders were terrorized through extortion and land-grabbing, generating a fear psychosis that allowed criminal enterprises to run smoothly.

Legal Consequences and the Gang's Enduring Legacy

The Chhota Shakeel gang's operations eventually drew the full weight of the state's legal machinery, particularly through the use of stringent anti-organized crime legislation. Rubina's case was fought by advocate Shahid Azmi, who years later, in February 2010, fell victim to a former shooter of the Chhota Rajan gang. The special MCOCA court convicted her for charges under MCOCA and 120 (b) (Conspiracy) of the IPC and sentenced her to five years of rigorous imprisonment on 23 March 2006. Her conceit and arrogance only seemed to increase during her years in jail, and the jail authorities were regularly inundated with complaints from prison inmates against her for assaulting them. Among the most prominent of these cases was when Rubina, along with her cellmate and Gateway blast-accused Fahmida Sayyed, attacked a diminutive Zahira Sheikh, who was serving out her perjury sentence in the Gujarat Best Bakery case. Following this, jail authorities punished Rubina by barring her from buying jail canteen coupons, which otherwise provided inmates access to luxury goods such as soaps, biscuits, toothpaste, and dry fruit. The gang's legacy, however, extends beyond its legal entanglements. The book's narrative emphasizes that within the gangs of the Chhotas, one finds clones galore, but rarely a woman who dared to stand up against the mafia, a reference to figures like Sapna Didi, who was given a dastardly death by the don's acolytes, with four of her twenty-two stab wounds specifically targeted at her private parts as a grisly warning to other women. The Chhota Shakeel gang, in its incorporation of women like Rubina, thus represents a complex and often brutal chapter in the history of Mumbai's underworld, one where gender dynamics and criminal power were deeply and dangerously intertwined.