O'Romeo: The Real Story Of Hussain Ustara And Sapna

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February 10, 2026 12:28 IST

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In O'Romeo, Shahid Kapoor plays dreaded gangster Hussain Ustara, whose life has been touched upon in S Hussain Zaidi and Jane Borges' book Mafia Queens.

IMAGE: Shahid Kapoor in O'Romeo.

Key Points

  • Vishal Bhardwaj's new film O'Romeo reportedly traces the lives of gangsters Hussain Ustara and Sapna Didi.
  • Shahid Kapoor and Triptii Dimri play the leads.
  • Hussain Ustara and Sapna Didi united against Dawood Ibrahim but failed to eliminate him.

Vishal Bhardwaj documents one of the most unsettling chapters of Mumbai's underworld history in his latest film, O'Romeo. Starring Shahid Kapoor, the trailer packs in a lot of action, drama and even tender romance.

Shahid plays dreaded gangster Hussain Ustara, whose life has been touched upon in S Hussain Zaidi and Jane Borges' book Mafia Queens.

Syed Firdaus Ashraf gives us a glimpse at who Hussain Ustara was and the lady he was in love with, Sapna Didi.

IMAGE: Shahid Kapoor in O'Romeo.

The Hussain Ustara story

In the early 1990s, Mumbai lived under the shadow of organised crime. Gang rivalries, extortion networks and police encounters shaped daily life, while ganglord Dawood Ibrahim's diabolic syndicate operated with near impunity.

It was within this environment that Ashraf Khan lived a relatively private life as the wife of Mehmood Khan, a gangster affiliated with Dawood.

According to those familiar with Mehmood's activities, he had grown weary of the criminal world.

Marriage, they say, had given him the desire to quit the syndicate and rebuild his life away from crime.

Leaving the underworld, however, was rarely an option.

Before any exit could take shape, he traveled to Dubai to meet Dawood Ibrahim.

After meeting Dawood, he returned to India but was killed outside Mumbai airport in a police encounter.

The Ashraf story

Mumbai police Inspector Emanuel Amolik, who led the encounter, got rich praise for killing the gangster. But Mehmood's wife Ashraf felt the encounter had been done at Dawood's behest.

She went to court against Inspector Amolik, naively believing that if the cop was indicted, it would pave the way for Dawood to be extradited to India.

Those close to Ashraf describe a visible transformation after her husband Mehmood was slain in the encounter.

Grief gave way to anger, and anger hardened into resolve.

In her mind, Dawood Ibrahim stood at the apex of the system that killed her husband.

How Hussain Ustara got his name

IMAGE: Triptii Dimri in O'Romeo.

She asked Arun Gawli, one of Dawood's rivals, for help, but he turned her away.

Later, she came in contact with Hussain Ustara, a sharpshooter known for his skill and composure.

The suffix 'Ustara' (meaning razor) was added to his name at age 15 after he refused to part with his share of stolen money with the ring leader.

In the fight that followed, Hussain took out his ustara and sliced the ring leader's neck. That's how he got the name, Hussain Ustara.

How Ashraf became Sapna Didi

There was a common link between Ashraf and Hussain Ustara: Both were enemies of Dawood Ibrahim.

Ustara was a police informer and that is how Ashraf got in touch with him.

It was Ustara who rechristened Ashraf as Sapna, which eventually became Sapna Didi.

She asked whether he would teach her to use a gun as well as help her kill Dawood.

Ustara agreed to train her and join her in her mission.

This decision was influenced not just by the audacity of her plan but because Ustara had, by then, developed romantic feelings for Sapna; feelings that were never returned.

Sapna remained emotionally tethered to her deceased husband Mehmood, focused singularly on revenge.

For her, the training was preparation, not partnership.

How Hussain Ustara and Sapna Didi's bond collapsed

The duo carried out various activities in Mumbai as well as in Nepal, which damaged Dawood's smuggling syndicate.

They were a good team until one day, Ustara crossed a line and it led to the collapse of their relationship. This happened in 1991.

When Ashraf wanted to save herself from Dawood's men, Ustara attempted to initiate a physical relationship with her.

She rejected him, making it clear that she saw him only as a friend.

Harsh words were exchanged, and the partnership ended.

From that moment, Ashraf/Sapna chose to pursue her objective alone.

Her most audacious plan soon followed.

The Dawood Ibrahim assassination plan

Ashraf/Sapna intended to kill Dawood during an India-Pakistan cricket match in Sharjah.

The choice of venue was deliberate. Dawood was expected to attend in the VIP enclosure, surrounded by spectators and the media.

The plan relied on proximity rather than firepower.

Everyday objects -- umbrellas, glass bottles and stiletto heels -- were to be used as weapons by her accomplices.

She believed that Dawood would not be armed in a public space and that surprise could overcome security.

But the assassination attempt never took place.

Whether the plan was leaked, abandoned or intercepted remains unclear.

What is certain is that news of her intentions travelled quickly through underworld channels.

Ashraf/Sapna had crossed an invisible but decisive line which angered Dawood's lieutenant, Chhota Shakeel.

How Sapna Didi was killed

In 1994, Dawood's men arrived at Ashraf/Sapna's Nagpada residence in central Mumbai.

She was dragged down the stairs and stabbed 22 times.

Investigators believe the brutality was intentional, designed to ensure that the killing would be remembered.

The message was unambiguous. This was what awaited anyone who dared to contemplate an attack on Dawood Ibrahim.

No verified photograph of Ashraf Khan is known to exist today.

Her face has vanished from police records, leaving behind only testimony, files and fragments of memory.

The end of Hussain Ustara

Hussain Ustara told author S Hussain Zaidi that he carried her photograph in his heart.

Four years later, on September 11, 1998, Ustara met his end.

Eight Dawood henchmen men shot him in the same Nagpada locality where Ashraf/Sapna had been slain.

Photographs curated by Satish Bodas/Rediff

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