Craig Calcaterra: Leaving Law, Baseball Analytics, and Writing Honestly About the World

Craig Calcaterra is the author of Cup of Coffee, a daily newsletter about baseball and pretty much everything else. In this episode, Craig traces the unlikely path from litigation attorney to sports blogger to NBC Sports writer to newsletter creator—and talks honestly about the luck, timing, and self-sabotage that shaped all of it.They talk about writing authentically when the world feels overwhelming, how sabermetrics changed baseball and then started to ruin it, his book Rethinking Fandom, and the strange feeling of being genuinely content with your work.