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The ex-con who had once plotted to kidnap David Letterman's infant son while working as a painter on the talk show host's Montana ranch has succeeded in executing yet another jaw-dropping maneuver straight out of the Depression-Era Crime Movie Playbook: He escaped with another inmate from the Montana State Prison where he was being held, and, four days later, the two are still on the run:

Offers of help came the New York Police Department and the U.S. Department of Homeland Security as officials continued searching for two missing, Montana State Prison inmates, one accused of bilking television personality David Letterman.

Sunday marked the third day of the Deer Lodge Valley search launched after staff determined Kelly A. Frank, 45, and William J. Willcutt, 22, were missing from the prison ranch. New information indicated the pair "may be armed and have other provisions to sustain themselves," according to a prison news release. Warden Mike Mahoney, contacted Sunday at the prison in Deer Lodge, declined to provide specifics.

The Smoking Gun has a refresher on the preparations Frank had made in anticipation of the kidnapping, including chilling details like fact that he had keys to Letterman's home, and precise knowledge of where the crib was located. Even more bizarrely, the kidnapping charges were eventually dropped in exchange for him pleading guilty to felony theft, essentially putting Frank away for ten years for overcharging Letterman for his painting services. The case is sure to shed unkind light on Montana's criminal justice system and its bumbling attempts at keeping dangerous criminals off the streets—they just might want to swallow their pride and accept the help of the NYPD and federal agencies, before Frank has the chance to ask another celebrity to pay way too much for his painting and deck-staining services again.