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Craig Calcaterra

I write Cup of Coffee, a daily baseball, politics, entertainment, and nonsense newsletter.

Pastrami on Rye

Cup of Coffee: October 22, 2026

The Miz gets the nod, Timeless Tickets, Suzuki is out, Cashman re-ups, an AI ballgame broadcast, Bearsketball, ex-pat remorse, wax museums, and the best sandwich

A storefront in Amsterdam that says "You're my morning coffee"

Cup of Coffee: October 21, 2026

Rays celebrate winning the pennant

Cup of Coffee: October 20, 2026

Drew Rasmussen yelling on the mound

Cup of Coffee: October 19, 2026

Ashby of the Brewers celebrates the final out

Cup of Coffee: October 16, 2026

Jake Bauers hitting a two-run homer

Cup of Coffee: October 15, 2026

The Brewers are up 3-0, what I think will happen with the lockout and why the fate of the Dodgers has nothing to do with it, earliest baseball memories, and finding joy

Freddy Peralta yelling. in triumph

Cup of Coffee: October 14, 2026