David Letterman has dodged quite a few bullets throughout the course of his decades-long career. Crispin Glover very nearly kicked him in the face in 1987, and years later, he unknowingly pulled a prank on a ruthless cartel leader with a reputation for killing people at the drop of a hat. One of the scariest close calls Letterman dealt with, however, occurred off-screen in 2005. That’s when the late-night host found out about an alleged plot to kidnap his 16-month-old son, Harry.
In March of that year, Letterman and his future wife, Regina Lasko, were alerted by authorities that a painter who’d worked at their home in Montana was planning to extort them. Kelly Allen Frank reportedly revealed to an acquaintance that he was going to kidnap Letterman’s infant son and his nanny and hold them for $5 million ransom. Mike Ferriter of the Montana Department of Corrections told CBS News, “The thought was to kidnap the nanny and the child so the nanny could take care of the child during this period of the kidnapping.”
Frank’s acquaintance informed the authorities, and Frank was arrested on charges of solicitation to kidnap. After making a deal with prosecutors, the kidnapping charges were dropped, and he pleaded guilty to a felony theft charge for overcharging Letterman for the painting he’d done for him. Frank also pleaded guilty to obstruction after lying to an FBI agent and wound up getting a 10-year prison sentence.
Following his initial arrest, Frank’s fiancée spoke in his defense, saying that he was joking about the kidnapping plot and swearing he “would never do anything to harm someone.” That statement seems to conflict with pretty much everything else that’s been reported about Frank, though. He was accused of rape before the Letterman situation and was convicted in 1999 for holding a woman against her will. He was released from prison in 2014 and has been arrested more than once since then. One of those arrests was for allegedly threatening to kill somebody in 2019.
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