4,000 days of prayer: A man’s journey out of Chicago street violence to a trucking convoy honoring the Feast of Our Lady of Guadalupe

It’s easy to fall back into a life surrounded by gangs, drugs and violence in the streets of Chicago after being released from prison, Juan Romero wrote in an essay from the four walls of his cell as he tried to understand how he landed there and how he could find his way out.

“It’s the only way of life we know,” said Romero, 36, now a free man.

He was in his early teens when first arrested. It was also then when he held a gun. At 19, he pulled the trigger and at 21, he was sentenced to 13 years in prison for attempted murder.

For a long time, Romero didn’t think there was a way out, especially after being convicted. Growing up in Pilsen in the ’90s meant that most of his friends, even his family, were intertwined in it. His older brother had been killed on 18th Street.

Solace and clarity came through prayer, he said.

Last week, a little over four years after serving his sentence, he adorned the hood of the semi-truck he drives for work with an image of ‘La Guadalupana’ — the Virgin Mary — to partake in the annual procession of truckers from Chicago’s South Side to the Shrine of Our Lady of Guadalupe in Des Plaines.

The convoy celebrates their faith and gratitude for answered prayers throughout the year.

Since he was released from prison in October 2019, Romero commemorates the Feast of Our Lady of Guadalupe every December with hundreds of other truckers in a pilgrimage the weekend preceding the holiday, on Dec 12. They join thousands of devotees who visit the shrine walking, running, biking and horse riding, making the Midwest celebration the second largest one after Mexico City and the Des Plaines shrine the most visited monument of its kind in the U.S.

This year, the Archdiocese of Chicago expects 400,000 people to visit the shrine, which houses the first replica of the sacred tilma — cloak — with the image of Our Lady of Guadalupe. Before it was brought to the Chicago area, the Des Plaines icon was touched to the original image and blessed at the Basilica of Our Lady of Guadalupe in Mexico City.

Though Romero detached from religion at a very early age, he said it was thanks to prayers that he found a second chance at life.

Sometimes he still finds his new life difficult to believe, but when he feels the breeze of the open road as he drives through different states, it settles in him. “It’s beautiful,” Romero said. “I’m grateful that people look at a different side of me now and not my background.”

When released from prison, he said he couldn’t find a job even after getting a commercial drivers licence. He lost all faith. But then he met Jose Ramirez and Maria Vargas, the couple who hired him as a truck driver at Mainland Corp., their family-owned flatbed transportation company.

“I’m glad I stayed focused. I’m glad I didn’t give up,” Romero said. His partner, two children, his mother and two of his siblings joined him in the procession this year. The six huddled inside the truck and smiled, excited to be there.

His mother, Maria Romero, who raised the family Catholic, said that she had prayed for that moment many times.

‘Is this the life that I want?’

Romero grew up in Pilsen. Though it now faces strong tints of gentrification and gang activity is stagnant, “back then, the bad influence around you was automatic,” he recalled.

Despite it all, he managed to graduate from Benito Juarez High School. And even though he had hardworking Mexican immigrant parents, he gravitated toward trouble, following in the footsteps of his older siblings.

That is something he is still trying to make sense of: “My parents gave me everything I needed, they supported me but I still took a different route,” he said.

It was when his older brother, Eddie Romero, was killed at age 22 that he took a step back.

“Is this the life that I want?” Romero asked himself knowing that going forward all he could do was deal with the consequences. “That lifestyle only leads to two places: death or incarceration,” he said.

In April 2009, he was sentenced to 13 years in prison. After 11 years behind bars at the Illinois River Correctional Center in downstate Canton, he was released in October 2019.

While incarcerated, his mother would visit him once or twice a year, but it was disheartening to see her that way, he said. So he spent his time reading, drawing and taking college courses.

He completed three vocational programs, including restaurant management, culinary arts and contribution. Romero also got an associate degree from Lake Land College. Following his release, he enrolled in driving school, after learning of the opportunities it could bring.

But despite the resume he’d built, he said his criminal record wouldn’t let him get ahead.

Until the day he heard that Ramirez and Vargas needed a driver. He called them.

“I told them my story, I didn’t want to hide anything,” Romero said.

“They didn’t judge me, they understood.”

At Mainland, at least 60% of drivers are formerly incarcerated men, said Vargas, co-founder of the company. The number of drivers ranges from eight to 12 throughout the year. Hiring them is something Vargas holds close to her heart and one of the reasons why her faith in Our Lady of Guadalupe is so strong. It allows them a new start.

Vargas was only 4 years old when her father was sentenced to 15 years in prison for drug-related charges and after being released, he was immediately deported to Mexico, negating a chance to return to his family.

Her father’s absence hurt her “in more ways than you can imagine,” Vargas said.

“I wish my father had had the opportunity to start over. Maybe today, things would have been different if the government, if society gave former prisoners a second chance at life,” Vargas said.

That is the reason why she and her husband hire people like Romero. He underwent six months of training and the couple hired Romero in November 2020.

That same year, Vargas invited Romero to participate in the pilgrimage she has organized every December since 2015 to commemorate the Feast of Lady of Guadalupe. They hire a mariachi to kick off the celebration and along with her aunts, she makes about 1,500 tamales to give to drivers who participate.

This year, more than 120 truck drivers took part in the convoy. Most make the journey to the shrine to fulfill a promise — a manda — or give thanks to the Virgin Mary for her blessings. For others, it is a prayer for a specific need or concern.

Vargas said that her journey this year is not only one of gratitude but also a plea. The workload has been unfortunately low this year and the diesel prices are extremely high. “But the company has managed to stay afloat,” Vargas said.

“Prayers work. I’m convinced that Our Lady of Guadalupe considers all of our sacrifices.”

Romero said he was never very religious. He stopped praying around the time he began to get in trouble.

But he leaned on faith after he lost his older brother. He wasn’t convinced it worked until he was released from prison and life, once again, put him to the test.

“There’s always hope. Don’t lose faith,” Romero said.

He is mostly grateful that he still has a family and they are together once again.

All after more than 4,000 days of prayer.

larodriguez@chicagotribune.com