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The Unseen Collision: How the School-to-Prison Pipeline and AI Are Quietly Forging a Disposable Class

AI didn’t create inequality. It’s just accelerating the consequences. We should deal with this now.

Author

Jim Stroud
May 11th, 2025

In this issue:

Fair warning—this one's darker than usual. Someone hit me with the phrase “school-to-prison pipeline” and, well… that was all it took. I went headfirst down a rabbit hole that I wish didn’t exist. What I found wasn’t pretty. But it matters. A lot. And by the end of this, I think you’ll see why.

But first—something to balance the scales.

A reader dropped this gem in my inbox after last week’s issue (which, by the way, you’d already have if you were on the email list. Just saying. Newsletters hit the inbox first.)

Here’s what they said:

I was so-ooo happy to get your article! You distill like Jack Daniel.

Not gonna lie—felt that. Almost slapped it on my arm as a tattoo. (Still might.) More likely? Slap it on a T-shirt and prance around like a lounge singer. Either way… much love to you. You know who you are.

Alright—enough warm fuzzies. Let’s get into the heavy stuff.

Brought to you by the fine folks at Recruiting Innovation Summit — where you figure out what’s next for talent acquisition, meet people worth knowing… and, yeah, where the karaoke gets a little dangerous. (I see a duet in my future. Looking at you - Jennifer Jones, MHR. )

The Unseen Collision: How the School-to-Prison Pipeline and AI Are Quietly Forging a Disposable Class

Before AI ever learned to write emails or steal jobs, another machine was already running — quieter, colder, and far deadlier for those caught in its teeth.

It didn’t need algorithms or automation. It needed something simpler: discipline codes, handcuffs, and permanent records.

Call it what it is — the school-to-prison pipeline.

A system built not to reform, but to remove. It didn’t just punish mistakes. It cut kids loose early — from classrooms, from opportunity, from the chance to even try.

For decades, this machine has worked as intended. Shoving vulnerable students into dead ends. Leaving them under-skilled, over-criminalized, and locked out of stable careers before they even became adults.

And now? That same forgotten group is running straight into AI’s blade.

Automation isn’t replacing them. It’s confirming their erasure.

For them, this won’t be a fight for jobs. It’ll be a fight to matter at all.

How Opportunity Gets Cut Off Early

This isn’t theory. It’s well-documented. Predictable. Brutal.

Zero-tolerance rules. Suspensions over vague offenses. Cops stationed in hallways instead of counselors. School becomes less about learning — more about removing problems.

Miss just 15 days of school in a year, and you’re seven times more likely to drop out later. Dropouts face limited work prospects — and juvenile records make that path even narrower.

The school-to-prison pipeline doesn’t just push students out of education. It pushes them out of the economy.

AI Makes It Worse

AI didn’t create inequality. It’s just accelerating the consequences.

By 2030, automation could displace up to 800 million workers globally. Generative AI alone puts 300 million full-time jobs worldwide at risk.

Which jobs go first?

These were fallback roles for many. AI is eliminating them.

Meanwhile, new roles demand critical thinking, digital skills, and adaptability — areas pipeline victims were never prepared for.

AI won’t disrupt them. It will lock them out entirely.

Why DEI and Reskilling Aren’t Enough

Corporate responses sound nice on paper:

  • DEI

  • Reskilling

  • Inclusive hiring

But they don’t address the starting point.

You can’t reskill people who never gained basic skills. You can’t hire what isn’t there.

Even Black Americans with some college face unemployment similar to white workers without diplomas.

Reskilling assumes readiness. DEI kicks in too late. The damage happens long before resumes are submitted.

The Way Out — Tough, Not Pretty

This isn’t about charity or social experiments. It’s about economic survival.

1️. Incentivize Second-Chance Hiring

  • Offer tax credits and regulatory relief for companies willing to take risks.

  • Make hiring overlooked workers a smart business move.

2️. Teach AI-Resistant Skills

Focus on:

  • Practical trades

  • Soft skills (reliability, problem-solving)

  • Basic digital literacy

Give alternative paths (cough-cough - blue collar jobs) the respect they deserve.

3️. Reward Private Sector Leaders

No mandates — just rewards.

  • Contract preferences

  • Public recognition

  • Tax incentives

Make workforce reinvestment profitable.

4️. Clean Slates — But Earned

Tie expungement to:

  • Workforce training

  • Stable employment

  • Community contributions

Offer redemption — but expect responsibility.

The Price of Ignoring This Will Be High

The school-to-prison pipeline already sidelined millions. AI will make that exclusion permanent unless something changes.

This isn’t about politics. It’s about workforce survival.

Fixing this isn’t optional. It’s the cost of keeping society — and the economy — intact.

Some doors, once closed, don’t reopen. We’re almost at that threshold.

The Comics Section

One more thing before I go...

I’ve got my takes on this stuff, sure. But when the conversation turns to equity and DEI, I defer to the pros.

They crushed it at the Recruiting Innovation Summit in Vegas last month. Pulled no punches. Said the quiet parts out loud.

If you really want to dive deeper (or get hit with something that might make you squirm in a good way), reach out to them. They don’t do boring.

Next issue, I'm lightening things up. Going to get jiggy with it. Tee-hee. Stay tuned.