Gretchen Schuldt

Arrested at 14, Still in Jail at 40

Kenneth Gray has served 25 years for reckless homicide. Is that long enough?

By , Wisconsin Justice Initiative - Mar 28th, 2021 12:42 pm
Green Bay Correctional Institution. Photo from the Department of Corrections.

Green Bay Correctional Institution. Photo from the Department of Corrections.

Kenneth Gray

Kenneth Gray

Kenneth Gray was at a house where he sold cocaine when he took a silver gun from his pocket, pulled the trigger once, and killed a man.

It was Dec. 30, 1995. Gray was 14 years old.

The victim was an adult drug dealer angry that young Gray was working in a Milwaukee neighborhood the man considered his own.

Gray, still in prison, now is 40. He has been incarcerated for almost twice as many years as he was alive when he committed his crime. His 30-year sentence ends in 2026. He is hoping to be paroled before then.

Here is what then-Assistant District Attorney Carol Kraft said in 1996 at Gray’s sentencing for first-degree reckless homicide. Gray was 15.

He, up until he became involved in the drug trafficking…by all the information that I had, wasn’t the type of child who had involved himself in these kind of activities and who would have been expected or – I guess one would have predicted to become involved in the events that occurred that day….

Unlike so many people we see, who at the age he came to the criminal justice system have long rap sheets, have many contacts with the police, Mr. Gray was not one of those people. Mr. Gray also doesn’t appear to have come from a family where this would have been expected. And I’m sure this is probably difficult for his mother who has supported him through this.

Gray’s prison life hasn’t been smooth. He’s had dozens of disciplinary infractions, some of them serious. He’s been transferred back and forth between institutions. But now, he says, he wants to get out and go to college, maybe get his pilot’s license. He likes to write, and he has written about his experiences: He talks about his mandatory release date in the piece below. That is a presumptive parole date that come two-thirds of the way through a prison sentence. The Department of Corrections, however, can decide to keep a person in its care beyond that date.


By Kenneth Gray

Here I sit, 4½ years past my mandatory release date (19 July 2016). This is after I’ve served 22 years of a 30-year sentence that was given to me at the age of 15 years old.

The judge forecast I’d be released early, before 20-year mark MR set by legislation, based upon overcrowdedness of the prison as well as my age. However, the Wisconsin Parole Commission has had other ideas.

When I was first locked up, after juvie and being waived into adult court, I was sent back to Juvie Hall because I was too young to be shipped to the Big House. There I spent 10 months in segregation because by law I was an “adult,” yet couldn’t be in the general population with other adults. Once I turned sweet 16, off to prison I went.

I have committed ‘violations of trust’ against the community, its people, and my family with utter disregard for any consequence.

And for that reason I’m on this bus, with this seeming only one-way ticket to prison. There were four of us all under the age of 21. We all possessed a certain level of trepidation. We were “fresh meat,” first-timers like me. Others had small stints in juvie for a couple months, but this trip here we all “kissed the baby.”

​We got off the bus shackled from head to feet inside the tan walls of Green Bay Correctional Institution, “Gladiator School” to those of us inside. The home of the Packers, Titletown. The closest I’ll ever get to Lambeau Field is rec on the yard – you can glimpse it. I’m not a Packers fan.

Entering the North Cell Hall, the sergeant warned each of us, “I don’t want no fuckin’ or fightin’. I’m doing no paperwork and if I do, something of yours will be broken.”

I quickly got the picture. You could smell smoke – cigarettes, marijuana permeated my new home. So did music. I was told “B-70” was where I was to go. Here I am without a parent or anyone to watch over me…in the “joint.”

My crimes started out with petty store theft of candy and the like. Quickly I’d matriculated to clothes, cars, anything that wasn’t nailed down. I saw a profit in crack sells. Though I was only 13 years old, I possessed the American entrepreneurial spirit. At that time I couldn’t spell the word or even knew of its existence, yet I’d diligently practiced it. My goals were to stop asking my mother for coins and attend high school driving my own vehicle instead of a stolen one…the aims of a young’un. Now I made this twin bunk hard as the steel and concrete that made up this cell. This bunk, no matter what Cell Hall, Unit, Bloc Pod, no matter what prison: Max, Medium, Super Max, Minimum, I would be laying down and waking in for the next generation, always on the same side, the wrong damn one!

My dwellings were a sink, toilet, small cabinet, wooden writing desk with a chair. I sat down and just listened to the conversations on the tiers, the voices of the penitentiary…scared. I was given neither direction nor manual on how to survive in this alien world…sink or swim.

The next morning I was allowed to ring my mother. Her worst fears – her first-born in prison for murder. She asked what I am allowed to have to said to keep my head up so when the time came I would be let out – oh, how wrong was she.

I was sent to the South Cell Hall, where the young men went to school and kept the powers-that-be on edge. Yeah, gangbanging happened day in and day out, fights every time “the bars broke.” It was the land that Pinocchio found himself in. Now I don’t liken myself to Pinocchio, though I was a boy in search for some realness, some authenticity in my life. No father was searching for me. I am on my own.

I’d completed my high school equivalency degree, a vocational in cabinetry, two other vocationals, though an inmate is only allowed to participate in one. I pursued knowledge. It was my savior. Knowing the unknown and not the least bit intimidated by what I might discover. Through all of these decades, books, knowledge has kept me in the realm of sanity. In moments of utter depression reading a book or two has kept my hope together.

​Unlike other states’ Department of Corrections, Wis-con-state doesn’t have “lateral transfers,” meaning an inmate can request a transfer to another joint of the same custody level…(In Max) if I went for some time without any misconduct, which was nearly impossible, I’d get my custody level bump and get sent to one of three medium institutions. After being there for about two and getting denied by – yep, you’ve guessed it – parole, I’d do something to get transferred, mostly always back to Max.

I was to serve seven years before I was eligible to be seen by Parole and technically eligible for release. No one is paroled or released their first time before the board. I was given a 24-month defer my first and second appearances.

Then the 12-month defer followed by four in a row – 18 years of being resentenced on the same case! Of being told, “No, you can’t go home.” It go to the point when I realized that I will not be paroled, so I waived going before them for five years.

I have been accepted to the University of Wisconsin–Oshkosh for their Film/TV/Radio program. I have completed ALL required programs within this DOC and then some, which was acknowledged by the Parole Commission. I am depleting taxpayer’s funds by sitting here in this prison.

At every follow-up hearing, I’m consistently denied release, despite being in prison since I was practically a baby. The excuse is “for further protection of the public.” The crazy part is, the public doesn’t even know I exist.

The phrase “lost in the system” can be applied here. I’ve written to organizations from Honolulu to Helsinki, and with every reply, if there comes one, it begins with, “Unfortunately…we’re unable to be of some assistance.”

I’m among the youngest convicted who’ve been imprisoned the longest.

I’m someone you never knew existed.

Gretchen Schuldt writes a blog for Wisconsin Justice Initiative, whose mission is “To improve the quality of justice in Wisconsin by educating the public about legal issues and encouraging civic engagement in and debate about the judicial system and its operation.”

One thought on “Analysis: Arrested at 14, Still in Jail at 40”

  1. jatraneKitties says:

    Kenneth Grey – I know you exist. You killed the father of two young boys. Their ages were 1 and 2 years old at the time. They will never know their father because you murdered him. Per your own writings, you have done nothing to redeem yourself during your 25 year incarceration or admit the crime that imprisoned you. That’s very sad.

Leave a Reply

You must be an Urban Milwaukee member to leave a comment. Membership, which includes a host of perks, including an ad-free website, tickets to marquee events like Summerfest, the Wisconsin State Fair and the Florentine Opera, a better photo browser and access to members-only, behind-the-scenes tours, starts at $9/month. Learn more.

Join now and cancel anytime.

If you are an existing member, sign-in to leave a comment.

Have questions? Need to report an error? Contact Us