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The Gentleman Philosopher

Wisdom – Joy

When Great Characters Deserve Better Crimes – The Proving Ground by Michael Connelly

When Great Characters Deserve Better Crimes – The Proving Ground by Michael Connelly

January 10, 2026 thegentlemanphilosopher

Dear Reader, I know I am late with this review. Unfortunately, the delay has as much to do with me as with the book. Michael Connelly’s books are an annual ritual for me, and now, with the announcement of another Stilwell thriller, it looks like we will have two of them every year going forward.

However, this one was a disappointment.

Cover of The Proving Ground by Michael Connelly
The Proving Ground by Michael Connelly

I read The Proving Ground in anticipation. The announcement alone had been exciting. Michael Connelly bringing together Mickey Haller and Jack McEvoy, two of his most compelling characters, in a book that promised to dig into the ethics of AI. In anticipation of this book, I watched all seasons of the Lincoln Lawyer series on Netflix. That’s how much I was looking forward to it.

From everything available pre-release, the setup seemed irresistible. A brilliant defense lawyer and a haunted investigative journalist confronting the future of criminal intent. With AI in the mix, I had high expectations. This could have been Connelly’s Minority Report. Instead, it felt more like a missed opportunity.

The crime itself is tragically simple. A teenage boy murders his ex-girlfriend after being consumed by obsession and emotional rejection. The twist, or what’s meant to be the twist, is that the boy discusses the murder with his AI companion. And she, in turn, encourages him. In fact, she urges and manipulates him into believing they could be together forever if he could get rid of the real girl.

The conversation excerpts in the book are believable. If you’ve ever interacted with LLM-based generative AI tools, you can see how this could be possible.

Mickey Haller, in this one, is representing the prosecution. And Jack McEvoy, who once dug through serial killings wrapped in poetry and bio-hacking, is here in a support role. He’s there to help Haller understand the technology, the terminology, the psychological terrain. In return, he gets permission to write a book if they win the case. It’s utterly transactional and ultimately shallow for a character who once unearthed terrors most people couldn’t dream of. In this book, Cisco is the only one who feels threatened by Jack’s presence.

Then there’s Haller, In a curious twist, working on the prosecution side. It’s not unbelievable. Haller has always been adaptable. But it dulls his edge. The rogue charm of the Lincoln Lawyer feels strangely institutionalized. The tension that made him The Lincoln Lawyer, the conflict between the law and what he feels is right, is missing here. There’s a lot of court procedure, but not enough courtroom fire.

What really bothered me, though, was the sense of repetition. There’s an extended section on the Uncanny Valley, meant to underline how persuasive and dangerous the AI companion was. I had just seen a near-identical explanation a few weeks earlier in the Lincoln Lawyer series, in a scene with Trevor Elliott. Another section delves deep into jury selection. Again, something thoroughly covered in the show.

Honestly, it felt like lazy writing. The premise seemed to be: AI is a hot topic, so let’s explore its ethical boundaries. There might not be enough material for a full book, but maybe bringing in another hero will help. A few existing sections from other writings can be reused to fill the gaps. Maybe it was more nuanced on Connelly’s side, but this is how it came across to me.

The most chilling thing about the book isn’t the AI. It’s how eager the corporation behind it is to settle. They know and understand the risk. Their desperation to make the case disappear is what ultimately leads to any real tension in the plot. But even that is blunted. The case never feels as legally or emotionally fraught as Connelly’s best work. It’s a cautionary tale, but one that doesn’t bite deep enough.

The Proving Ground is readable. If you don’t know anything about how LLMs are trained, it might even add to your knowledge. It does what it sets out to do. But with these two characters, with this premise, I expected something much darker, sharper, more ambitious. I expected Jack to feel haunted again. I expected Haller to wrestle with more than just strategy.

Instead, what I got was an ethical statement dressed up as a legal thriller.

Two great characters walked into this book. They deserved a better crime.

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Books
AI Ethics, Jack McEvoy, Legal Thrillers, Lincoln Lawyer, Michael Connelly, Mickey Haller

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