Spy magazine has returned on Substack with a limited “Spy at 40” series that is republishing vintage pieces about Donald Trump, and its Substack page invites readers to “sign up to get a month of daily posts in October & November.”
The Substack publication, titled “Spy at 40,” is posting archived Spy stories about Trump, with individual items on the site dated to original issues such as October 1986 and linked as daily posts; the Substack display shows posts titled “Trump, Proud Tenant Evictor and Vexatious Litigant” and “Guess Who’s One of the 10 Most Embarrassing New Yorkers?” with recent Substack timestamps.

Kurt Andersen, co-founder of the original Spy, told Boing Boing that the 40th-anniversary celebration will “start publishing starting next Monday the 5th, a limited series of daily excerpts and links from the magazine’s archive, with bits of new commentary and context.”
The Substack home page frames the run as an “Anniversary Chronicle of a Certain Short-Fingered Vulgarian” and lists multiple archive posts, showing the publisher is reissuing original material alongside small amounts of new context.

The return is temporary and themed: Boing Boing reports the team will publish a limited daily series drawn from Spy’s archive, and the Substack’s subscribe prompt explicitly promises a month of daily posts across October and November.
Why it matters: Spy’s archive helped popularize recurring satire of Trump in the 1980s, and this reissue places that material back in circulation during a high-profile moment for the former president; readers interested in contemporary Trump coverage may find historical context in the republished pieces.
For related coverage on the current political landscape and platforms where Trump appears, see internal reporting such as Trump latest: CNN roundup of key US political coverage and Trump Truth Social: how to find his posts and the platform’s updates.
Sources
- Spy Magazine (Substack) — Substack home page announcing “Spy at 40,” listing archive posts and the line “Sign up to get a month of daily posts in October & November.”
- Boing Boing — Kurt Andersen quote and reporting that the limited series will “start publishing starting next Monday the 5th, a limited series of daily excerpts and links from the magazine’s archive.”











