The strangest and saddest saga in the life of David Letterman involves Margaret Mary Ray, a deeply disturbed woman who spent years stalking him. She first made headlines in 1988 when she was arrested when she didn’t pay a $3 toll — while driving Letterman’s Porsche, which she’d just stolen, insisting to officers that she was his wife.
In subsequent years, Ray continued to harass Letterman and was arrested on numerous occasions while trespassing on the property of Letterman’s Connecticut home. She ultimately spent 10 months in prison and then an additional 14 months in a psychiatric facility. Letterman responded with concern — for both his own well-being, and hers. “The thing is, she’s insane,” Letterman told the Stamford Advocate, via Tulsa World. “And you don’t want to do anything to make it worse than it is.” According to Letterman, he’d come to the end of his rope in how to deal with her. “It’s been five years now, and I’ve tried a lot of things, and none of them have worked.”
Eventually, she turned her attention from Letterman to retired astronaut Story Musgrave. When she was arrested for trespassing at his Florida home, reported the Los Angeles Times, Musgrave told authorities that she’d been stalking him for the past four years. In 1998, Ray took her own life when she kneeled in front of an oncoming train.
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