Thanks only to a deal with federal prosecutors, the 65-year-old probably won't finish it in a prison cell.
A Seattle resident, Shepard was caught in one of the more troubling drug crimes imaginable - he was dealing powerful prescription painkillers to addicts he courted through treatment programs. For a healthier man, the federal drug crime conviction that followed would almost certainly have meant prison time.
Wounded at war and having spent much of his life on the street, Shepard is barely mobile and suffering from severe heart trouble. Though they had him dead to rights - he sold more than 800 pills to an undercover police officer, and admitted to the whole mess shortly after his arrest - federal prosecutors in Seattle have asked that Shepard receive probation.
"Although he appears to have viewed himself as providing some kind of service to the community, in fact he preyed on the vulnerable by selling prescription narcotics to drug addicts, thus fueling the very disease they sought to escape," Assistant U.S. Attorney Kate Vaughan said in court papers.
"But for his severe and deteriorating medical condition," the federal prosecutor continued, "he would be incarcerated."
Police caught wind of Shepard's drug dealing in November 2012, when officers learned he was selling painkillers out of Nomadian Community Resource Center in Seattle's Hillman City neighborhood. Shepard owned the non-profit center, which hosted Alcoholics Anonymous and Narcotics Anonymous meetings.
Undercover officers posed as addicts in treatment to gain Shepard's trust. While Shepard refused to sell the drugs during the meetings, he was willing to do so immediately afterward.
Speaking with an undercover officer, Shepard compared the members-only center to a Masonic club. He refused to sell to recent inductees and appeared concerned - justifiably, it turned out - that "rats" would inform on him to police.
Shepard ultimately admitted to selling prescription painkillers to "members" of the non-profit. The members, who also attended treatment meetings at the Orcas Street center, were given ID numbers used in the drug deals.
Among the drugs Shepard sold were narcotics - oxycodone, hydrocodone, morphine and methadone - that many of the treatment clients were presumably hoping to break away from.
Law enforcement agents searched the center in March 2013, seizing drugs as well as two pistols from Shepard's bedroom.
While the actual scope of his operation remains unclear, Shepard told an undercover officer that the Nomadian Community Resource Center had 2,000 members. Shepard sold 862 pills to undercover Seattle police officers and Drug Enforcement Administration agents over eight drug deals.
Shepard's own trouble with drugs began at birth and continued throughout his life.
Born to a drug-addicted mother, Shepard spent time in foster care before joining the U.S. Army in 1966. He was 17.
Sent to Vietnam, Shepard was awarded the Purple Heart after he was blown out of a helicopter. Despite his wounds, he was dishonorably discharged after he was caught stealing.
Shepard left the Army behind, but not the drug addiction he'd acquired there, his attorney said in court papers.
"I was mentally beat up with a drug habit," Shepard told his attorney, according to court filings.
In the years that followed, Shepard was either high - he used heroin before turning to crack cocaine - or incarcerated. Sometimes hospitalized for schizophrenia, Shepard was often homeless and usually without work.
Predictably, Shepard's health has declined dramatically as he has aged. He is nearly immobile due to heart problems and other maladies; he is currently eligible for an artificial heart, which he would not receive in prison.
"To incarcerate Mr. Shepard would undoubtedly accelerate his death," defense attorney Jesse Cantor said in court papers.
"He simply does not pose a danger to the community," Cantor continued. "He spends most of his day either sleeping or at the hospital. Mr. Shepard is not in any condition that would cause one to be concerned that perhaps he would repeat his offenses."
Under the sentencing recommendation brought forward by prosecutors and the defense, Shepard would be sentenced to two years under house arrest and three years on probation.
Shepard is scheduled to be sentenced Friday morning by U.S. District Judge John Coughenour.