Running Against the Devil by Rick Wilson

Unsubtle, uneven, and I couldn’t stop listening

If you read Rick Wilson’s first book, Everything Trump Touches Dies, you already have a good idea of what to expect with this one: uncompromising political commentary, repetitive and sometimes grating insult comedy, and some fascinating insight into electoral strategy and persuasive messaging.

Rick is at his best when he focuses on things he knows well: How to calibrate messaging to reach the right political audience, electoral pitfalls to avoid, and the science and strategy of political advertising. If Rick wrote a book on how to design the perfect political ad, I’d buy it in a heartbeat. He argues persuasively in this book how the Democrats should take on Trump, and lays out a convincing plan that had me nodding along in spite of my more progressive politics. It’s excellent inside baseball analysis from a guy who’s helped his clients win a lot of close elections, and worth the price of admission.

Rick is at his worst when he’s trying to be funny via insults. The joke bits between sections where he writes tweets from Trump’s possible second term and a dialog between Trumpian focus group participants are awkward rather than humorous, and work better as horror than comedy (maybe that was the point?). Rick is fluent in enough pop culture and internet meme references that he can be engaging, but I don’t think his gags are clever enough to achieve the laughs he’s going for. These humor flails don’t derail the book, but I seriously considered skipping forward 30 seconds at these points.

The last problem I had with this book is that Rick often falls into the trap of repeating himself rather than explaining. We get it Rick, you think Bernie Sanders is a communist, Democrats are awful at state-specific politics, and woke culture is the ruin of the Donkey party. Repeating warnings makes some sense (e.g. The Electoral College is all that matters), but Rick’s lack of empathy for the tens of millions of people who live in big cities and favor progressive politics means that he doesn’t spill a lot of ink on how people who believe these things on the left can make an argument for them. To Rick, it’s just not worth the discussion, other than to tell you it’s a waste of time and a sure loser. Then again, he’s been a diehard conservative for about as long as I’ve been alive, so I guess this might be asking too much.

All told, I blazed through this book and felt passionate enough about it to write a review. Easy to recommend for anyone interested in the crazy politics of 2020.

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