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A Madison man who pleaded guilty in May to a drug delivery charge, related to the heroin and fentanyl overdose death of a Lodi man in 2017, will spend six months in jail as part of a sentence of probation that depends heavily on his own behavior over the next three years to avoid going to prison.

Dane County Circuit Judge Nicholas McNamara on Tuesday told Jeffrey D. Skidmore, 48, that if Skidmore’s probation is revoked over the next three years, he’ll automatically and immediately begin serving a five-year prison sentence, without having another hearing before McNamara.

McNamara sentenced Skidmore to five years in prison and three years of extended supervision for delivery of heroin, but ordered the sentence suspended and placed Skidmore on probation for three years. As a condition of his probation, Skidmore must serve six months of his probation in the Dane County Jail. McNamara ordered that the jail portion of the probation be served immediately — not starting in weeks or months as is customary — “to help you understand the degree of unpredictability of your choices,” he said.

The sentence, McNamara said, takes into account Skidmore’s prior criminal history, but also the fact that Skidmore has had no monitoring rules violations while free on bail since his arrest.

Skidmore was charged in May 2018 with first-degree reckless homicide for the December 2017 death of Charles J. Cisewski, 27, who died after he injected a combination of heroin and fentanyl that Skidmore sold in Monona to a friend of Cisewski. Under a plea agreement this May, Skidmore pleaded guilty to delivery of heroin, and the homicide charge was dismissed.

Family members of Cisewski told McNamara that though he was not perfect, and suffered from the addiction that ultimately cost him his life, he was a good man who loved his family, the outdoors, fishing and hunting, playing guitar and cooking.

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His mother, Roberta Paepke, said she still has crab legs in her freezer that her son had planned to cook for them, and still cares for the dog, Coco, that her son left behind.

“I will grieve for my son for the rest of my life,” Paepke said.

Skidmore’s girlfriend, Ariel Viken, tearfully told McNamara that Skidmore, who used heroin himself, has changed a lot since December 2017, including staying sober and helping her get her business off the ground. Since learning of the death of Cisewski — someone Skidmore never even met — he has often cried himself to sleep, she said.

Assistant District Attorney Valerian Powell asked McNamara to sentence Skidmore to three to five years in prison, while Skidmore’s lawyer, state Assistant Public Defender Tracey Lencioni, asked for a suspended sentence and probation, though for different periods than McNamara ultimately set.

Skidmore said that even though he never met Cisewski, “it doesn’t mean that I don’t feel awful about this.”

“I’m sorry, I’m so sorry,” he said to Cisewski’s family.

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