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While
working on a story about the effects of child abuse, MacIntyre met a young
criminal named Tyrone Conn who had experienced abandonment and deprivation
in a series of foster families. 
After the story, Conn kept in touch with MacIntyre and his colleague, producer Theresa Burke. Assuming he would never be professionally involved with Conn again, MacIntyre became a surrogate big brother, doing his best to help the young man whenever he could.
In 1999, while
a prisoner at the maximum security Kingston Penitentiary, Conn sparked
a media frenzy when he became the first prisoner in 40 years to escape.
Two weeks later, when the police surrounded his Toronto hideout, a desperate
Conn called his friends at the fifth estate. Theresa Burke tried in vain
to calm the young man down over the phone and then listened in horror
to the shotgun blast that ended his life.
"I didn't quite know how to deal with it at first," MacIntyre says. "We knew that his life and death raised a lot of really important questions. Did my friendship with him handicap my ability to do a story about the system? Many old-time journalists would have said I was the worst person to do it. I thought, I know more about his life and death and that system than anyone else, so why shouldn't I tell the story? As with any story, whether it's in a newspaper or on television, it succeeds or fails in the eyes of the audience. And nobody has yet told me that this story failed."