Forty-four years ago, five Afro-Caribbean men stormed a ritzy Rockefeller-owned country club on the island of St. Croix and murdered eight wealthy individuals – seven of whom were white – in an execution-style shooting. The murders would racially divide the small nation, one of the U.S. Virgin Islands, and contribute to the decline of a once-booming tourism industry.

After a contentious trial, where it was argued that the accused were politically motivated, Ismail Muslim Ali (formerly Ishmael Labeet) and his four co-defendants were convicted of eight counts of first-degree murder and sentenced to serve eight consecutive life terms.

On New Years Eve in 1984, after countless failed attempts to overturn his conviction, Ali would hijack an American Airlines plane full of passengers and take asylum in Cuba, where he’s lived freely with his wife and children since.

The Skyjacker’s Tale director Jamie Kastner

With unprecedented access to one of the FBI’s most-wanted fugitives, veteran filmmaker Jamie Kastner‘s 75-minute docu-thriller, The Skyjacker’s Tale, focuses on the contemporary framework around Ali’s secretive life in Cuba and how he’s now threatened with extradition to the U.S. more than 30 years later.

Produced by Kastner’s Cave 7 Productions, the film further provides jumping-off points to investigate the 1972 crime, the turbulent trial that ensued in the U.S. Virgin Islands and the later skyjacking, while revealing the racially charged police tactics used in an attempt to force confessions.

Bell Media-owned Canal D and pay-TV network Super Channel were the first broadcasters to board the documentary – which premieres Saturday, Sept. 10 at the Toronto International Film Festival – after acquiring the Canadian TV rights the film in 2014.

The film marks Kastner’s third project with Canal D and his first production deal with the pay-TV broadcaster.

The deals came months after Kastner was awarded CAD$300,000 (US$274,500) in funding from the Canada Media Fund’s POV fund, after pitching the film at the Hot Docs Forum, and awarded an initial grant of $11,000 in development funding from the Shaw Media Hot Docs Fund.

Toronto-based design studio and sales house Agency 71 has since joined the doc as Canadian theatrical distributors, while Kastner’s Cave 7 will handle the film’s international distribution.

Kastner’s most recent film, The Secret Disco Revolution, premiered at TIFF in Toronto in 2012. His other docs include Kike Like Me, Djangomania! and Free Trade is Killing My Mother. 

Ahead of Saturday’s debut, Kastner talked to realscreen about his approach to the sensitive subject matter, utilization of reenactments as a storytelling method and the reasons behind Cave 7′s jump into film distribution.

This interview has been edited and condensed for clarity and length. 

You rely somewhat heavily on re-enactments, particularly to recreate the robbery. Was there any hesitation in using that method to tell a comprehensive story in a documentary?

I don’t think I lean that heavily on recreation, [but] I’m proud of the recreations and I’ve gotten very positive responses. Recreations have been in and out of fashion for the amount of time I’ve been making films, and beyond that. When I started out, it would have seemed completely forbidden to do anything so cheesy as a recreation.

To me, recreations are just another color on the palette and why limit yourself? That’s like saying, ‘I’m not going to use the color red.’

That said, I did have trepidation. I did not want to make cheesy recreations and it’s a real danger. In the end, I would have been comfortable using more recreations given how well these ones turned out.

What were some of the production challenges that you encountered throughout the project?

Penetrating – as a white guy from Toronto – a fraught, poor black community in the Caribbean and getting them to open up about their most notorious crime, which everybody on the island still blames to this day for having ruined tourism on the island, was challenging.

You’re navigating two countries that are old Cold War enemies – the U.S. and Cuba – so that means navigating a whole bunch of sensitivities. It’s a minefield of vested interests at every turn, so it was nothing but challenging.

Can you tell me about the decision behind why you’re moving into film distribution? 

I’ve become known for having done very well pre-selling my own films internationally in the past. I have worked with great sales agents in the past, and, through a combination of that, and my own regular market activities, I have built a wide range of solid relationships. Now that my wife Laura Baron Kastner, a former corporate lawyer and entrepreneur, has joined the company, adding some serious business heft, we have begun producing and exec-producing the work of other filmmakers as well as my own. It seemed like a natural step.

Has the film acquired any sort of distribution heading into TIFF?

The interest in this film going into TIFF is unprecedented in my experience, and I’ve had films that have launched pretty big for Canadian docs. I had a film that launched with eOne at TIFF in 2012, Secret Disco Revolution; and when Kike Like Me launched at Hot Docs in 2007, it was the top-selling film of the festival that year. The interest in Skyjacker’s Tale, I feel that sometimes you just get lucky.

Agency 71 has picked it up as Canadian theatrical distributors, and I’m very excited to be working with them in this capacity. My company, Cave 7 Productions, is handling the international distribution.

• The Skyjacker’s Tale holds its world premiere on Sept. 10 at 9:30 p.m. EST at Hot Docs Ted Rogers Cinema.