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.

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Compliance

The Play — Issue #26: The Redlines Lawyers Turn Down

Oct 19, 2026

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6 min read

The Play — Issue #26: The Redlines Lawyers Turn Down

Microsoft's Copilot for Legal and the suggestions lawyers reject, two courts split on an expert's ChatGPT history, and Meta's new terms for your firm's website.

Matthew Roberts

Articles

Compliance

Oct 19, 2026

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6 min read

The Play — Issue #26: The Redlines Lawyers Turn Down

Microsoft's Copilot for Legal and the suggestions lawyers reject, two courts split on an expert's ChatGPT history, and Meta's new terms for your firm's website.

Matthew Roberts

Compliance

The Play — Issue #25: Harvey Drafts the Motion. A Lawyer Picks the Arguments.

Oct 12, 2026

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5 min read

The Play — Issue #25: Harvey Drafts the Motion. A Lawyer Picks the Arguments.

Harvey and LexisNexis automate the motion to dismiss, AT&T turns its legal department into an agency, sorting 10,000 documents drops below two dollars, and Vorys builds AI versions of 36 partners.

Matthew Roberts

Compliance

The Play — Issue #24: Six Contracts, €1,000, Back the Same Day

Oct 5, 2026

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9 min read

The Play — Issue #24: Six Contracts, €1,000, Back the Same Day

One cntract playbook and a stopwatch, the disclosure sentence California now requires, OpenAI's notices and its new agents, and the AI reading briefs from the bench.

Matthew Roberts

Compliance

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

Compliance

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

Compliance

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