The Most Expensive DUI in Massachusetts History

In what could be seen as the most expensive DUI in Massachusetts history, Karen Read was found Not Guilty this week of second-degree murder in the death of her boyfriend, Boston Police Officer John O’Keefe. The Commonwealth claimed she’d run him over in a drunken rage and left him to die in the snow. But from the start, the story didn’t add up.

By Blair Hopkins. Narrated by Alex Andrews

O’Keefe’s body was discovered in front of another cop’s house—after a party packed with off-duty law enforcement. His injuries showed clear signs of both blunt force trauma and hypothermia. The house was never processed as a crime scene. Witnesses changed their stories. Evidence went missing. And despite a mountain of red flags pointing to the people inside that house, the investigation zeroed in on one person: Karen Read.

Her defense argued what more and more people began to suspect—she was being framed, and the entire justice apparatus was working to protect the officers involved. This wasn’t a flawed investigation. It was a coordinated cover-up. The cops at the party. The cops handling the evidence. The cops feeding the media. All of them worked together to protect the badge, not the truth.

But here’s the difference: Karen Read had access to something most people never will. A million-dollar defense. A high-profile “Hollywood” lawyer. A national audience ready to rally in the comments. And an image that worked in her favor—white, conventionally attractive, upper-middle class. Even with all that, it still took two trials and an internet army just to get her justice.

Meanwhile, women like Donna Castleberry never got a chance to tell their side of the story.

In 2018, Castleberry—an Ohio mother—was shot six times by undercover Columbus Vice officer Andrew Mitchell in the back seat of his unmarked car. She had just discovered he was a cop posing as a sex buyer and tried to flee. The police narrative immediately painted her as violent, unstable, and criminal. But it came out later that Mitchell had a pattern of abuse, and that Castleberry’s killing fit a disturbing pattern of misconduct.

He wasn’t arrested until years later. And even then, it took enormous community pressure to get the case before a jury.

Or take Donna Sanford, who was charged in 2020 after surviving a brutal encounter with law enforcement. She wasn’t protected, believed, or supported—she was prosecuted. Her trauma became the State’s motive. Her resistance became a threat. And her story? All but erased.

These are the women the system devours when no one is watching. Black women. Sex workers. Survivors. Women with records. Women without resources. Women who don’t “look good” in the courtroom or on the evening news. Women like Donna Castleberry and Donna Sanford don’t get trending hashtags. They get death, charges, and silence.

I’ve met dozens of these women. I’ve answered their jail calls. I’ve listened as they described abuse at the hands of the same officers who later showed up in court to testify against them. Their records are weaponized. Their pain is ignored. And their truth is called “unreliable” by the very people responsible for the harm.

And that’s what makes the Karen Read case so stark.

Because when someone like Read is put on trial, and the whole nation is watching, the mask slips. The public sees what many of us already knew: the police don’t investigate themselves—they protect themselves. This case didn’t prove that the justice system works. It proved how hard it tries not to.

From missing phones to contradictory testimony to “accidental” evidence tampering, this wasn’t law and order—it was institutional loyalty disguised as prosecution. It only fell apart because Karen Read had the resources to fight back.

But justice shouldn’t be a luxury item. The truth shouldn’t depend on your ability to afford it.

That’s why we fight. That’s why we organize. That’s why we show up for the women who never make the front page.

If you want to make sure the next Donna Castleberry or Donna Sanford has someone in their corner, someone to fund their defense and tell their story—donate to swopbehindbars.org.

We defend the people they try to disappear.We back the ones the State wants silenced.And we’re building a world where the blue wall doesn’t get the last word.

👉 Because the next Karen Read won’t have TikTok on her side.

But she still deserves to walk free.