Riley served in the Army after graduating high school in 1971 and later became a follower of the Grateful Dead.

Over 15 years in the 1970s and 1980s, Riley says he regularly used, shared, and sometimes sold drugs to fellow Deadheads. On four occasions, he pleaded guilty to charges involving small amounts of marijuana, hashish, and amphetamines; he was incarcerated for short periods in county jails in California and Wisconsin for two of these offenses.483 Each of these convictions arose out of activities outside of Grateful Dead shows. Riley also maintained jobs at a paper mill in Northern California, where he worked as a dockworker, truck driver, and warehouse laborer. He married and had two children.

In 1993, Riley was convicted in a federal court in Iowa of conspiracy to distribute LSD. Prosecutors alleged that he had mailed or delivered LSD and psychedelic mushrooms to other Deadheads. According to Riley, one of his co-defendants cooperated with authorities against him in order to avoid a life sentence.484 The recipient of two mailings of small amounts of LSD also testified against Riley at trial, and both co-defendants were sentenced to much shorter terms than Riley.

Riley was held accountable for more than 10 grams of a “mixture or substance” of LSD, a threshold amount that triggers a mandatory minimum sentence of life in prison without the possibility of parole on a third offense. In determining the amount of drugs for which Riley was responsible for sentencing purposes, the judge counted the weight of the blotter paper on which the LSD was dissolved, in addition to the miniscule weight of the actual drug he had mailed. The judge also held him accountable for amounts of LSD testified to by the cooperating witnesses, even though there was no physical evidence these drugs existed.

Because the prosecutor filed for statutory sentencing enhancement based on Riley’s two prior felony convictions for possession of 1.75 grams and 5.25 grams of marijuana with intent to distribute, Riley was sentenced to mandatory life without parole under the recidivist provision of the 1986 Anti-Drug Abuse Act, a sentence Riley calls “murderers’ time.”485 According to Riley, without the statutory sentencing enhancement for his prior convictions, his sentencing range under the United States Sentencing Guidelines would have been 27 to 34 months.

At sentencing, Judge Ronald Longstaff told Riley, “The mandatory life sentence as applied to you is not just, it’s an unfair sentence, and I find it very distasteful to have to impose it…. I agree with one thing you said…about the laws of Congress… keeping me from being a judge right now in your case, because they’re not letting me impose what I think would be a fair sentence.”487 Judge Longstaff added, “[E]ven though this is a life sentence, I want it made clear that…it’s one the Judge was very dissatisfied in imposing. And Mr. Riley is not a threat in terms of violence.”488 Judge Longstaff later told a law professor that he believed that a 10- to 12-year sentence would have been appropriate in Riley’s case.

Judge Longstaff, an appointee of former President George H. W. Bush, wrote nine years later, in 2002, in support of Riley’s commutation petition, “Given the circumstances of Mr. Riley’s case, it was difficult for me to impose the required life sentence. To this day, it remains the harshest punishment I have imposed as a district court judge. There was no evidence presented in Mr. Riley’s case to indicate that he was a violent offender or would be in the future. It gives me no satisfaction that a gentle person such as Mr. Riley will remain in prison the rest of his life.”490 Riley’s commutation petition was not granted.

Riley said at his sentencing hearing, “Today I will see the remainder of my life stand in forfeit.”491 He added, “I stand before this Court today with no choice but to promise to allow the Federal Government of the United States to spend freely, and unendingly, the money of the taxpayers…that they will spend each year to protect and isolate the American people from me.”

Riley refers to himself as a “dead man” because of his life-without-parole sentence and says that “the horror of a life term” is “to not be able to see an end.”493 Since his incarceration nearly two decades ago, his father has died and his mother has been afflicted with Alzheimer’s. He spends his time writing poetry and studying the Upanishads and the writings of Friedrich Nietzsche.

Click here to view original ACLU article (Page 87).

*Robert’s sentence was ultimately commuted by President Obama after serving more than 25 years behind bars.