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Compliance

+3

The Play — Issue #23: Fifty-Four Percent, and That Was the Good Number

Sep 28, 2026

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10 min read

The Play — Issue #23: Fifty-Four Percent, and That Was the Good Number

A private answer key for grading legal AI, four vendor defaults that flip in thirty days, a token price cut that may not lower the bill, and what OpenAI's own agents did last week.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #22: Slowing Down AI?

Sep 15, 2026

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7 min read

The Play — Issue #22: Slowing Down AI?

An evaluator who does not report to the buyer, Latham's own GPU servers, Morgan & Morgan's four percent, and the gap between using AI and deploying it.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #21: The Fix Never Reached the Template

Sep 11, 2026

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6 min read

The Play — Issue #21: The Fix Never Reached the Template

Four plays: fake citations that lived in a go-by, a filing whose metadata named its author, a D.C. judge's cite-check model against California's, and ChatGPT's forward-only off switch.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #20: The Safe Harbor Your Email Server Closed

Aug 31, 2026

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7 min read

The Play — Issue #20: The Safe Harbor Your Email Server Closed

Four plays: Rule 11 service you can prove, the reprimand that never expires, California's last day, and the fake law arriving from the other side.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #19: Your Legal AI Vendor Is Now a Connector

Aug 26, 2026

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7 min read

The Play — Issue #19: Your Legal AI Vendor Is Now a Connector

Four Points: renegotiate before you sign, read what California actually amended, fix the taxonomy the connector inherits, and watch who is building the plumbing.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #18: Every Citation Was Real

Aug 24, 2026

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6 min read

The Play — Issue #18: Every Citation Was Real

Four plays: a position check your cite-check cannot run, the appendix that ended a case, twenty-five dollars a client, and a sanction the lawyer cannot bill.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #17: The Notetaker Kept a Copy for Itself

Aug 17, 2026

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8 min read

The Play — Issue #17: The Notetaker Kept a Copy for Itself

A federal court drew the line between a tool and a party, and Otter landed on the wrong side. Plus the legal AI tool nobody vetted, and a mark inside your drafts.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #16: Your Vendor Has Vendors

Aug 12, 2026

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6 min read

The Play — Issue #16: Your Vendor Has Vendors

The LexisNexis outage happened on somebody else's servers. Plus the NYC Bar on recording anyone who isn't your client, and the model providers moving into implementation.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #15: The Agent Didn't Access Anything. You Did.

Aug 10, 2026

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5 min read

The Play — Issue #15: The Agent Didn't Access Anything. You Did.

Matthew Roberts
Matthew Roberts
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The Play Newsletter

Practical AI for law firm operators. Not theory, not vendor pitches. What's going on and what's actually working, from someone running it.

© 2026 The Play Newsletter.
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