He spent 17 years behind bars. Now, he’s determined to help those still inside prepare for release.

by Erin McGroarty

Some say time freezes when you go to prison. That the age you are when you go in lingers in a way when you get out. 


Those close to Shannon Ross describe him as possessing the wisdom of an old man, but the drive of a 19-year-old. 


That was the age Ross was when he began a 17-year prison sentence for a homicide conviction.


While inside, Ross read piles of books, completed his undergraduate degree in business administration and began a newsletter for other incarcerated people that would later morph into the successful reentry nonprofit he runs today.


“My time in prison was just a lot of focusing on my future and staying in society,” Ross says. “It was very comfortable for me to return to society, because I never allowed myself to become comfortable while I was inside.” 


Ross’ determination inside was born of a resilience and passion he describes as core to his personality as a whole; a “natural personality” for which he credits his family. 


The smooth reentry Ross experienced is not always the case for many leaving the prison system, and society’s narrative of negativity and fear surrounding formerly incarcerated people only adds to the barriers they face as they strive for belonging again. 

Ross was released from prison just over two years ago. Now, he’s pushing for the change he sees as vital in the ways society responds to people with criminal records.


He speaks with passion for a cause, deep compassion for others and a level of maturity one can only develop through years of personal growth and reflection.

Shannon Ross is the executive director of The Community, a nonprofit based in Milwaukee that helps those still in prison prepare for release. Photography by Perri Moran.

Origins and belonging

Ross was incarcerated for 17 years and was released in September 2020. He launched The Community in 2014 which he was still in prison. The Community began as a newsletter for fellow incarcerated people with information about reentry. Photo courtesy of Shannon Ross.

Ross grew up in a part of North Milwaukee he jokingly describes as “hood adjacent.” On the corner block of North and 47th, he remembers a good childhood, as the only child in a loving family.


He has brown eyes and a bright smile – the kind that may have faded from others after 17 years behind bars but remains for Ross as a symbol of his resilience and hope for the future. 


But, coming from a biracial background and growing up in a largely Black neighborhood, Ross recalls getting made fun of a lot as a child.


“When I shave and I don’t have any facial hair, I look very young. And so especially when I was younger, and that was the case, I would get a lot of comments about being gay and a lot of jokes about that,” he says. “Growing up in the neighborhood where I already was very fair skinned, I would get the white comments and the gay comments in a Black neighborhood, in a very hyper-masculine culture.”


The bullying contributed to Ross feeling of a lack of belonging, adding a chip to his shoulder and a need to prove himself that later led down the path to his crime. 


Ross has since learned to embrace this sense of placelessness. 


“I don’t think I’ve ever really felt a sense of belonging anywhere, but I’m very happy about that now because it allows me to belong everywhere in a sense,” he says.


Ross was imprisoned at nine different facilities across the Wisconsin Correctional System throughout his 17-year sentence. 


The first six years, he was incarcerated at Dodge Correctional Institution in Waupun, only about an hour drive from Milwaukee and still close enough for family to visit. Ross was able to see his parents close to every week during this time. 


He was later transferred to Stanley Correctional Institution in Chippewa County. This prison was much further away, and his parents weren’t able to travel the 250 miles more than once a year. 


At that point though, Ross had fostered a bond with his parents that could last the mileage and ultimately, he saw the time further away as a chance to focus on himself and his goals.


“That season change in my journey through prison was kind of appropriate,” Ross says. “I needed to get away from seeing people. I needed to focus more on some of the programs and opportunities that were at this new prison.”


During his time at Stanley, Ross completed distance education courses from UW–Platteville, a program he learned about through his cellmate, Jeremy Taylor. These courses later contributed to Ross earning his undergraduate degree from Adams State University while serving time at Oakhill Correctional Institution in 2017.


“He was very driven and focused. And that was in all aspects of his life, even sports,” Taylor says. “Which is one of the reasons why I think we got along so well, because we understood each other.”


Taylor, also originally from Milwaukee, now runs a machine shop in Florida — a dream he built while in prison alongside Ross. When the two weren’t doing schoolwork or playing basketball together, they were making plans for what they would each accomplish upon release. 


“He had plans that he would bounce off me with regard to The Community, and I’d bounce ideas off of him about things with regard to the business that I intended to start,” Taylor says.

The Community

Ross began The Community — now a successful nonprofit aimed at easing the reentry process and providing resources for those recently released from prison — as a newsletter while he was still in prison. 


He wanted a way to share the information he was gathering on reentry and resources with other incarcerated people.


“People were confused about a lot of myths that exist in the prison system,” Ross says. “I would readily go out of my way to share resources, to get information for people. And it just seemed like a natural progression.”


The first issue was shared in December 2014 with the help of Ross’ mother, who previously worked in the newspaper world, and a man Ross had met in prison who was now released working in a copy shop and could help with design and printing. 


Ross produced the newsletter from within prison for six more years prior to his release. The two-year anniversary of his release fell the day after we spoke. 


The information in the newsletter was — and remains —  shaped around reentry, reform, decarceration, news and connections. 


A recent issue released in July 2022 focused on voting rights for people with criminal records. 


Ross’ goal is simple — to provide easily accessible, accurate information specifically for people in prison. 


When Ross was released from prison in September 2020, the newsletter had 8,000 readers. It is now read across the Wisconsin Prison System and accessed by thousands of other incarcerated people across the country, Ross says.


This effort, and the nonprofit itself, is central to who Ross has shaped himself to be after his own release, and his passion for the work is hard to ignore when he explains it. 


“Our work is really focused on trying to get people before they get out, and walking with them while they’re inside and meeting them where they are,” Ross says.

Correcting the narrative

The other half of The Community centers around a campaign called Correcting the Narrative. This campaign is made up of a series of video interviews with formerly incarcerated people sharing their stories of triumph, struggle and success. 


The goals are twofold and reside in the name. 


“It’s simply showcasing the successes, humanity and agency of people with criminal records, to focus on that storytelling so people with records can know their own empowerment,” Ross says. “But also people that don’t understand this demographic, how they can then also have a different view, a more accurate view, of this demographic. So the whole story, the correct story, is known.”


Kaleigh Atkinson does the film work for the Correcting the Narrative campaign, in which each video shares the story of one or two formerly incarcerated people. Atkinson met Ross about six months after his release while she was working on producing a podcast with her partner who was incarcerated in the state of Oregon.


The connection was immediate. 


“He always says you have to meet people where they are, and that’s a lot harder said than done, but he’s actually one person who I know when I’m having trouble I can go to because he can see all sides of it,” Atkinson says. “I think it’s imperative what he’s doing.”


Atkinson began this work while her partner was still incarcerated, and she described the sense of community she felt finding other people who had been impacted, personally or vicariously, by incarceration. Atkinson’s work with The Community not only helped the campaign, but also her. 


“It was so refreshing to meet Shannon and the community of people doing this type of work in Milwaukee, because I just didn’t know it existed,” Atkinson says.

"A wasteful system"

Ross has dedicated his life to helping those who are still in prison prepare for the day they get out. This work is crucial in Ross’ mind, particularly because, as he sees it, the prison system itself only widens the gap between those incarcerated and the rest of society.


“It’s made people rich who are already rich. It has made individuals that are in different parts of the society and are already separated by things like class and race and religion even more separated,” Ross says. 


The system, as it is currently run, preys on a thirst for punishment of those who have wronged us that is inherent to human nature.

That isn’t a solution, though, Ross says.


More than half of those formerly incarcerated are unable to find stable employment within their first year of return and three-fourths of them are rearrested within three years of release, according to data collected by The Brookings Institution, a nonpartisan think tank focused on social sciences research. 


Further research from the Brookings Institution has shown that access to “health, housing, skill development, mentorship, social networks, and the collaborative efforts of public and private organizations” is shown to vastly improve the reentry experience and reduce recidivism. 


“I think we found pretty significantly in social science that just pure punishment for people, it’s not an effective deterrent,” Ross says.


“There are effective ways to deter, there are effective ways to teach these lessons and keep people from doing certain things, but they require trust, they require empathy. We don’t have a system that does that. That system is very cold.”


For Ross, meaningful change in the way incarceration is approached in this country needs to come from within. 


“The system is absolutely a failure in pretty much every single way you can think of, but it also is very logical and human in the way it was developed and why it continues to exist,” Ross says. “And we need to acknowledge that if we’re really going to address it instead of just thinking that it’s some evil people out there that are running it, because it’s us. It’s not other people that are running the system.”

Graphic by Zoe Bendoff and Erin McGroarty. Featured photo courtesy of Shannon Ross.