How Jimmy Romans’s Life Went Up In Smoke

It was a Monday morning in mid-June, the day after Father’s Day 2011, when Jimmy Romans was indicted by the federal government for selling marijuana.

He had been part of a network of friends from the west side of Indianapolis that had distributed thousands of pounds of weed in the area between 2006 and 2010. Jimmy was a wholesaler, a middleman, supplying a few select retailers with bulk amounts of product. Ten months prior, in August of 2010, one of those retailers had been pinched with a pillow of pot by the Indiana State Police and offered a deal: turn confidential informant or take the rap for what’s in the trunk. A few weeks later, ISP had Jimmy on tape financing the deal of 24 pounds of weed.

The maximum penalty under Indiana law for dealing more than 10 pounds of marijuana was eight years. The prosecutor offered Jimmy a better option: plead guilty to the Class C felony and agree not to contest any of the property the police had seized—which was already sitting in a warehouse ready to be sold at the next county auction—and in return he could do two years in a work-release facility. The decision was a no-brainer.

Despite the events of the previous 10 months—Jimmy’s wife had filed for divorce a few months after his arrest—he was in high spirits that Monday morning in mid-June. The tall, skinny redhead was two months from being a free man—good behavior and clean drug tests had cut his sentence in half—and he’d spent the previous afternoon visiting at home with his parents and three children. It almost felt like old times.

Jimmy swung by the small place he was renting, like he did every morning on his way to work. He had just let the dog out when he heard a commotion from outside. Jimmy opened the door to see two van loads of federal agents leaping onto the lawn and charging toward the front porch.

“Hey, here I am,” Jimmy said, clueless. “I’m on work release. I haven’t done anything wrong.”

The agents told him about an indictment coming out of Texas.

“Texas?” he said. “I’ve never even been to Texas.”

Jimmy didn’t know it yet, and he wouldn’t fully understand for nearly two years, but he’d just been tossed into the rapids of the federal criminal justice system without a life vest.

Jimmy Romans began selling marijuana for the same reason as anyone who enters the drug game: it was his best chance at the 21st-century version of the American Dream. Which is to say that Jimmy was looking to get rich beyond his wildest imagination.

He’d grown up in a 925-square-foot house in an urban working-class neighborhood off 38th Street, right next to Lafayette Square Mall. His dad, James Sr., was a field-service engineer while his mom, Sue, worked at the church and cared for Jimmy and his younger sister, Liz.

“Jimmy was such a jokester,” Liz says. “He made friends with anybody and everybody.”

“Nobody was a stranger,” recalls James Sr.

Jimmy was a good athlete and a really great singer—he participated in every choir offered at Northwest High School. But he never applied himself academically and drifted through a steady flow of minimum-wage jobs after school. He got married in his early 20s, had a daughter, and got divorced. It was around that time, the mid-’90s, that he was caught breaking into a grocery store after hours and spent 180 days in the Marion County Jail.

In the intervening decade, Jimmy avoided any further legal trouble. But despite an honest effort—he built prefab homes, did excavation work, and even tried his hand at real estate—his financial situation never much improved. By the time the mid-2000s rolled around, Jimmy was an unemployed felon with child-support payments, a new wife, and a two-bedroom apartment he could barely furnish. That’s when he ran into an old childhood friend, a guy everybody called “Bob.” Jimmy and Bob had dealt in small amounts years before, but now Bob had a connection to semi-trucks full of Mexican weed. Jimmy jumped at the opportunity to make some real green. And boy did he have fun spending it.

It’s impossible to know how much weed Jimmy sold or how much money he made during the four years he middle-manned marijuana for the Mexican cartel. The government would later charge him with moving 22,000 pounds, which at roughly $1,000 per pound equals just over $20 million. It’s a gaudy, outlandish number, and according to Jimmy and his family it’s wildly, unbelievably exaggerated.

What about Jimmy’s situation wasn’t hyperbolic? The man enjoyed the hell out of his new lifestyle.

He bought cool cars, flashy jewelry, and floor-length furs. He filled his basement with enough sports collectibles to stock a retail store. He attended big sporting events, made trips to Vegas, and had been in the process of purchasing a vacation home in Florida. But at the same time, Jimmy had practically zero wealth. When he was arrested on the original state charge in Indiana, his seized assets totaled just over half a million dollars, not including the 6,000-square-foot red-brick behemoth his family had been living in (that house was still owned by Bob, who had moved to the Dallas metroplex the year before).

“My son had a money problem,” James Sr. says. “He didn’t know the value of it!”

Jimmy had always been bad with money, although often in a good way. He was very generous. When he was broke, for instance, he wouldn’t hesitate to put a dollar in a homeless man’s cup or let a friend crash for free in a house he was trying to rent out. It was the same way when he was flush, only it was hundred-dollar bills and all-expenses-paid vacations. In retrospect, it seemed like he was trying to karmically right his criminal wrongs, as if the flash of a thick roll could bribe the universe into looking the other way.

Jimmy donated anonymously to Riley Hospital for Children, dropped off toys and bikes to a local radio station every Christmas, and lavished his mom with a $7,000 catered Mother’s Day dinner. Once, after seeing the baseball fields he played on as a kid in disrepair, weeds overgrowing the infield and broken fence posts in the outfield, Jimmy found the director of the Little League and donated $5,000 to help restore the old ball fields. He wanted the kids he saw out there playing to have the same great memories of the place that he had.

But, of course, the universe can’t be bribed. And by the time Jimmy found himself on a bus headed to Fannin County Jail in dusty Bonham, Texas, he couldn’t even afford a lawyer.

“DOJ is basically like a football team that goes out on the field with razorblades and bicycle chains.”

Why was the government prosecuting Jimmy Romans in Texas, specifically East Texas, 800 miles from where he sold marijuana? The short answer: Because they could.

Jay Combs, Assistant U.S. Attorney for the Eastern District of Texas, looked out over the jury seated on wooden pews inside the century-old courthouse in Sherman, a city with a population of about 36,000—roughly the size of Plainfield—located near the Oklahoma border.

“A partnership in crime, ladies and gentlemen,” Combs told the jury. “That is what you’re going to hear about over the course of the coming days.”

It had been 15 months since Jimmy, along with 15 other co-conspirators from the Indianapolis area, were indicted by the government for conspiracy to distribute marijuana. While Jimmy had been putting his life back together following his state arrest, the Indiana State Police had continued their investigation. They had an informant who put them on to Bob, who was overseeing the operation from the Dallas area, and they’d intercepted a white cargo van on I-465 that was filled with 2,000 pounds of pot. The bust had attracted the attention of the DEA. It was dominoes from there.

The long answer as to why Jimmy was on trial in the Eastern District of Texas consists of two reasons. One is technical, the other inherent.

The first reason comes from a 1912 Supreme Court case, Hyde v. United States. The Sixth Amendment of the U.S. Constitution makes clear that a defendant accused of a crime has the right to stand trial before an impartial jury from the state and district in which the crime is alleged to have occurred. What the 101-year-old Hyde ruling did was create a loophole, allowing any overt act committed in furtherance of a criminal conspiracy to be tried in whatever district the act was committed.

It can be anything, really. Something as simple as a single member of a conspiracy receiving a traffic citation in a district is enough to implicate everyone in the entire conspiracy. Which is exactly what happened in Jimmy’s case: A U-Haul being used to move a member of the conspiracy down to Dallas to work as a money runner had been pulled over along the I-30 corridor in Texarkana, just inside the border of the Eastern District.

That was all that Jay Combs needed to prosecute the case. And he wasn’t the only one—the route that the U-Haul had taken from Indy to Dallas, which had been highlighted in an atlas the government recovered, gave seven other districts a venue claim. The Southern District of Indiana, at the time headed by current Indianapolis Mayor Joe Hogsett, would have made the most sense. But they declined to take it.

That created a situation where the federal agents who’d taken over the investigation from the Indiana State Police were then able to offer the case to federal prosecutors in the “just passing through” districts, a process known by critics as “venue shopping.”

The Eastern District of Texas was buying.

The second, less technical reason Jimmy was on trial in Texas had to do with the very nature of the federal criminal justice system itself.

“You have to understand the pathology of the process and the extent to which the criminal justice deck is stacked in favor of the government,” explains Clark Neily, vice president of criminal justice at the Cato Institute. “DOJ is basically like a football team that goes out on the field with razorblades and bicycle chains.” Federal prosecutors are given wide latitude and unchecked discretion during the early stages of a criminal investigation, says Neily. Moreover, his argument goes, they are incentivized to achieve speedy convictions. “Think of prosecutors as deer hunters competing to get the nicest rack on their wall. That’s how they get promoted within the organization.”

Which explains why, according to a 2018 study by the National Association of Criminal Defense Lawyers (NACDL), fewer than 3 percent of federal criminal cases result in a trial, while more than 97 percent are resolved by a plea agreement.

Of the 15 men from Indianapolis originally indicted, four of them, including Jimmy, opted to exercise their Sixth Amendment right.

It would become clear that the government was not pleased.

Jimmy’s court-appointed lawyer, James Whalen, had been practicing criminal law in Texas for nearly two decades. He knew that his client’s best chance was to contest the venue.

The trouble was that convincing a jury to acquit on what seemed like a technicality is a tough sell, particularly on a drug charge in very conservative, very pro–law enforcement Sherman, Texas.

The trial lasted three days.

The cops testified about the stop of the white cargo van, and how it had been spotted at Jimmy’s house on one occasion, and they brought with them photo evidence of all the toys and collectibles Jimmy had in his basement: 50 signed jerseys. Forty signed balls. A pair of boxing gloves autographed by Muhammad Ali. There was a partial picture of the 35 pairs of white Nike Air Force Ones in his closet, and Jimmy’s prized sheared beaver coat made an appearance.

As damning as the testimony from police was, it was the words from the other co-conspirators that sealed Jimmy’s fate. Especially his old childhood friend Bob, the original and main target of the federal investigation. (His forfeited assets included over $4.5 million in cash and five houses.) Bob, who had an extensive criminal record and had been caught lying under oath and coercing witnesses in a previous DWI case, had debriefed with the government 10 times before trial.

“Why did you plead guilty?” Combs asked at the beginning of his testimony.

“Because I felt like it was the right thing to do and I wanted to take responsibility for my actions,” Bob said. “I committed the crime.”

Over the course of two days, he laid out the inner workings of the organization he admitted to being the leader of. He told the jury how he’d stolen the Mexican connection from his previous dealer and was the point person between the source of supply and the streets of Indianapolis. Any money that was collected by Jimmy or other middlemen was sent to Bob, who kept all the receipts on an Excel spreadsheet that he diligently updated daily. He even told the jury about how it was Jimmy, a few years his senior, who’d introduced him to marijuana and taught him how to bag up $20 sacks when he was still a senior in high school. It was all very, very damning.

But it was Jimmy’s ex-wife, who’d been cooperating with investigators since the divorce, that really drove home the dagger. She testified about how years before—when she’d been pregnant with their second child—Jimmy had instructed her to move a heavy duffel bag that was full of marijuana. She also brought with her a note Jimmy had handwritten listing all the assets he once owned. Most importantly, and against all evidence to the contrary, she claimed that Bob and Jimmy were 50/50 partners.

Jimmy’s lawyer tried his best to remind the jury of the venue issue, at one point spending three minutes with Jimmy’s ex-wife trying to find Fishers, Indiana, on a map. And just as he had with every other witness the government presented, Whalen attempted to show that she had something substantial to gain for her testimony. Specifically, he pointed out that she was in the United States on a green card, and thus subject to expulsion from the country if charged with a crime.

It was an argument that fell on uncaring ears. The jury returned a guilty verdict first thing the next morning. And just like that, Jimmy was plunged back beneath the rapids of the justice system and propelled, frantic and gasping, toward the sound of crashing water.

The worst was yet to come.

Jimmy sat in stunned silence. He understood what Judge Crone was saying but was still numb to its full meaning.

Looming high on the bench in her black robes was the Honorable Marcia Crone. Judge Crone, deeply religious and strongly conservative, had been appointed to the federal bench by George W. Bush in 2003. As much power as federal prosecutors have in who gets charged with what, it is judges with lifetime appointments who hold the ultimate power in deciding the fate of a guilty defendant.

Judge Crone was considered a fair arbiter during the guilt-and-innocence phase of the trial. But when it came to sentencing, she wasn’t afraid to hit the top range of the recommended guidelines.

The way federal sentences are calculated is incredibly complex, yet the formula is something nearly every guilty defendant can recite verbatim and in excruciating detail. The simplest way to think of it is as a crime scorecard, in which a person’s criminal history combines with the elements of their new offense to equal a guideline for the judge to base their sentence upon.

Jimmy had a clean criminal history (the burglary charge was too far in the past to count against him), but prosecutors threw everything else they had at him. Bob claimed to have imported over 50,000 pounds, of which Jimmy was held responsible for 22,000 pounds—just enough to put him over the threshold to automatically trigger recommended sentencing of 30 years to life. Since the government also was charging him with operating a stash house and introducing an underage Bob to cannabis way back when, Jimmy’s sentencing guidelines came back with a recommendation of life imprisonment.

On behalf of the government, Jay Combs argued that the sentence was appropriate. Jimmy was not your “average player,” he said, citing all the evidence illustrating the luxurious lifestyle he’d lived. “In fact, there is much to show that he was a kingpin of a massive $40 million operation, and the sentencing guidelines reflect just that.”

Defense attorney James Whalen, on Jimmy’s behalf, countered that the sentence was excessive, that based on the facts of the case it would simply be for punishment’s sake alone. Whalen mentioned that voters in two states, Colorado and Washington, had recently approved the sale of marijuana for recreational use. He asked the court to consider the growing trend. He also pointed to the 12-year sentence that the leader of the conspiracy, Bob, had received. “I think to then sentence Mr. Romans to life in prison results in a significant sentencing disparity,” he said. “And it clearly, in my view, punishes Mr. Romans for exercising his right to a jury trial.”

Whalen was referring to what’s known as the “trial penalty,” the perceived discrepancy between what prosecutors will offer during a plea deal and what the sentence becomes after a trial. In fact, a 2018 study of sentencing data confirmed what the anecdotes suggested: The average post-trial sentence for guilty defendants is triple that of the average post-plea sentence, even when the crime is exactly the same.

“Your Honor, I have been doing this for long enough that I’ve had clients receive life sentences. And the one common denominator in all those cases is they murdered somebody.”

“Well,” Judge Crone responded, “you can get life for not murdering people.”

“I know you can, Your Honor. But to me this is not that case. And I think the fact they spent money does not justify a life sentence. The guidelines are wrong. I think a variance is appropriate.”

Judge Crone looked down upon the 40-year-old father of three sitting below her. Her mind was made up.
“Request for variance is denied,” she declared. “I think a life sentence is appropriate in this instance. The large quantity of drugs, the large quantity of funds, him getting other people involved in this lifestyle of crime and drugs.” The judge was boiling herself into a sermon, her righteousness spilling over the bench. “No matter what states are doing, I don’t agree with it. The federal government hasn’t changed the marijuana laws, and I think it’s misguided the states that have. So I don’t agree with that. And I’m not going to look at the trends.”

Jimmy sat in stunned silence. He understood what Judge Crone was saying but was still numb to its full meaning. James Whalen was all too aware.

“I was shocked,” he admits now. “A life sentence for marijuana—how in the world does that even comport to make sense? Especially in the age of legalization. If you’re importing that much heroin, okay, you have the potential to kill a lot of people. But marijuana? Nobody’s dead here.”

After reading the sentence aloud, Judge Crone briefly paused before adding insult to injury: “It is ordered that the defendant shall pay the United States a special assessment of $100 which is due and payable immediately.”
She’d given Jimmy a life sentence and charged him $100 for the privilege.

The gavel came down.

FMC Lexington sits high atop a hill overlooking the pastoral landscape of Eastern Kentucky. The imposing brick prison, with its towering concrete facade and layers of barbed wire, looks like something out of a Stephen King novel. It is Jimmy Romans’s home.

On a sunny Sunday morning this past January, not long before COVID-19 spread like wildfire through the prison, Jimmy Romans appeared in the visitor’s room looking heavier than when he’d gone in, with white whiskers speckled into his red stubble. He greeted a stranger like they were old friends.

“You ever been to federal prison before?” he asked, spreading his arms out wide to showcase the cramped visiting room. “Welcome!”

Jimmy had appealed Judge Crone’s decision but received no relief. He bounced around from one federal facility to the next over the following half-decade, holding the weight of his walking death sentence at bay while compiling certificates of self-improvement and a clean disciplinary record.

He received a break in 2017 thanks to legislation known as “Drugs Minus Two.” The amendment retroactively reduced the sentencing guidelines for drug trafficking offenses. Life without parole became 360 months, or 30 years. He is eligible for release in January of 2037.

For the Indiana State Police, their effort paid off. In addition to the half-million in assets they seized from Jimmy, they enjoyed a hefty slice of the federal forfeiture as well.

Down in Texas, Assistant U.S. Attorney Jay Combs was nominated for a national award for his work “prosecuting and investigating a significant drug trafficking organization.” Meanwhile, the courthouse in Sherman has since become a venue for trying Colombian drug cases.

Jimmy’s childhood friend Bob served five years and is now a free man.

Judge Marcia Crone is 68 and still sitting on the bench.

As for the trends, Jimmy’s lawyer asked her to consider: Medical marijuana is now available in over half the country, and voters in nine additional states have legalized recreational use since Jimmy was sentenced back in 2013. According to a recent Gallup poll, 66 percent of the country supports an end to federal prohibition.

The federal prison system is the nation’s largest jailer. It costs the government nearly $35,000 a year to house a single inmate. Almost half of its inhabitants are imprisoned on a drug trafficking conviction. For both humanitarian and budgetary reasons, there has been a strong bipartisan push to release nonviolent drug offenders from federal prison. The Trump administration even put together an informal task force, led by the president’s son-in-law and White House adviser Jared Kushner, to weigh in on clemency petitions. A nonprofit out of California has taken up Jimmy’s cause, and his paperwork has been submitted to the administration and is currently under review.

Back in the visitor’s room of his current home, Jimmy reflects on the choices that brought him there.

“I got too big for my britches,” he says. “I was greedy, man. But people make mistakes and life goes on, you know? My mistakes are going to last a lifetime.”

Jimmy has done the math. His two youngest kids, who he hasn’t seen since Father’s Day 2011, will be pushing 30 if he makes it to the end of his sentence. His two grandkids—he’s Papaw Jimmy now—will have graduated from high school. He may never see his parents as a free man again. Jimmy admits that he deserved to be in jail, but argues that he’s done his time: just 5 percent of marijuana offenders in the federal system are serving sentences longer than 20 years. All he’s asking, he says, is for a shot at the second half of his life, a chance to repair his broken relationships and prove to people that the man he used to be is not the man he’s become.

“President Trump can order my release with the swipe of a pen,” Jimmy says. “It’s in his hands right now.”

It is enough to keep hope alive.