Jamie Kastner Gets The First-Ever Interview With A Fugitive Hijacker In Cuba In ‘The Skyjacker’s Tale’

Before skyjacking became synonymous with suicidally smashing a plane into a building, there was something undeniably sexy about it. The idea that you could outrun your pedestrian problems, commandeer a jet, and fly off into your own personal promised land (and maybe stick it to The Man in the process) captivated many. Many more than most people remember, in fact: During the “golden age of hijacking,” between 1968 and 1973, planes were hijacked at the rate of nearly one per week. Sometimes, the hijackers even got away with it.

One of the lucky ones (or smart, or strategic, or crazy enough) was Ishmael Ali (formerly Ishmael Labeet). A self-professed black militant and member of a Black Panther faction from the Caribbean island of St. Croix, in 1984 Ali was on a flight from St. Croix back to the mainland where he was scheduled to serve out eight consecutive life sentences for his part in a shooting massacre that killed eight at a St. Croix golf course owned by the Rockafeller family. Despite being handcuffed and sandwiched between two air marshals, Ali somehow produced a pistol, commandeered the plane, and ordered the pilots to fly him to Cuba, where he’s lived ever since.

Some black revolutionaries of the era, who gravitated towards Marxism as it was obviously the opposite pole of world influence at the time — if you thought the U.S. were corrupt, imperialist warmongers, maybe the folks they were constantly demonizing actually weren’t so bad? — sought asylum in any overtly anti-American country that would have them, from Algiers to North Korea. There, as you might expect, they by and large had a bad time. By contrast, Ishmael Ali’s choice of Cuba seems to have worked out pretty well.

The free world hadn’t heard from Ali in 30-some years, until Canadian documentarian Jamie Kastner discovered him through random coincidence (tipped off by a friend of his mechanic, who had run into Ali while traveling to Cuba). Kastner, who had directed The Secret Disco Revolution and Kike Like Me, had no personal connections to either the Virgin Islands or Cuba, but he was smart enough to know a good story when it fell in his lap. So he set off to Cuba to find Ali and secure the first-ever interviews. Kastner profiles Ali in The Skyjacker’s Tale, playing this week at the Toronto International Film Festival.

Ali’s flight to freedom alone is a hell of a story, but that isn’t the half of it. There’s also the events that caused Ali (then Labeet) to become a dissident, the court case that made him a fugitive, and the 30 years in exile afterwards. Then there are the big questions. Ali maintains he never committed the murders he was convicted of in the first place, which led to a trial in which he was defended by famous radical lawyer William Kunstler before a judge appointed by Richard Nixon, in which confessions were alleged to have been procured using torture. Did he do it? When does righteous resistance become terrorism? Was Ali common criminal or revolutionary? And then there’s the coda: Will the U.S.’s warming relations with Cuba mean the end of Cuba as a safe haven? Do the Marxist-jargon spouting black revolutionaries of the ’70s have anything to teach today’s police brutality protesters? Any cautionary tales?

There’s a lot going on in The Skyjacker’s Tale, almost too much for one movie to handle. I got to pick Jamie Kastner’s brain about it while he tries to sell the film this week at TIFF.

How did you first hear about this story?

I came to this story completely at random through my car mechanic. I drive a 30-year-old Mercedes, beautiful clunker, that necessitates a close relationship with a mechanic. Fortunately, this mechanic is kind of an intellectual, politically minded guy, who one day said, “You do docs. I have a buddy who goes down to Cuba regularly, and uhm, he met this guy in a bar who hijacked a plane to get there.”