Despite the fact that marijuana is legal in Colorado and medical marijuana is legal in 20 states, there are still hundreds of marijuana convicts sitting in American jails. Even crazier? 25 of those prisoners are serving life sentences for marijuana convictions.

One particular story has captured my attention, because the prisoner-for-life hails from my home state of Indiana. In 2004, James Romans, a 42-year old divorced father of three from Indianapolis, was struggling to pay the bills with low-wage construction jobs. That is, until his childhood friends made him an offer he couldn’t refuse: if he would help them distribute marijuana shipped in from Mexico, he’d have no problem paying his bills.

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And for six years, he didn’t. But in 2010, Romans got busted with 27 pounds of weed. The court gave him a relatively light sentence, partially due to his single dad situation, ordering him to participate in a work release program for a year. But with just two weeks left in his sentence, Romans’ former associate (and long-time buddy) got busted in Texas for slinging weed. (Interesting sidenote: Romans’ friend, Eric Pieper, the alleged ring leader, was getting his PhD in Texas while running a major marijuana ring. Great solution to college loan debt.) The upshot: Romans was flown down to Texas and tried by the feds for conspiracy to distribute, which is a much more onerous charge.

But it gets worse. Many of the fifteen defendants in the case—all former buddies of Romans—had already cooperated with the feds, and thrown him under the bus. Romans claims they lied in order to get lighter sentences. Whether this is true or not, it doesn’t change the fact that Romans got royally screwed in the end.

Thanks to mandatory minimum laws, which the U.S. adopted in 1987—at the height of the crack epidemic—the sale of more than 10,000 kilos of marijuana qualifies as a very severe offense. (And keep in mind, these sales are estimated over many years.) And if a judge concludes that the defendant owned a gun “in furtherance” of the crime and operated a house where the drugs were kept, the level of offense ratchets up even higher. So when Romans’ judge, a notoriously remorseless woman named Marcia Crone, didn’t believe James Romans’ pleas that he was just a middle-man and his friends lied, she gave him a life sentence.

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This system of allowing drug offenders sentencing leniency for “cooperation” (which often involves lying) often ends up with one or two defendants getting a raw deal. And Romans got just that: he’s a gentle Midwestern guy in a maximum security prison, where one of his roommate’s was already brutally stabbed. But there may be hope yet. Romans’ lawyer, James Whalen—who we talked to for this Morning Show segment—says that a Supreme Court case may help his client in the court of appeals. United States vs. Booker was a 2005 ruling that said judges do not have to comply with sentencing guidelines. Romans’ fingers couldn’t be more tightly crossed. Because if his appellate judge isn’t buying the U.S. vs. Booker defense, he’ll never get to play outside with his kids again.

Ryan Nerz is the host of "The Cannabusiness Report" and the author of two books about American subcultures: "Eat This Book" (competitive eating) and "MARIJUANAMERICA" (weed culture). He lives in Miami.