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The Billboard That Failed

How not to write a political ad

3 min readJul 21, 2025

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Oakland held a special mayoral election on April 15 — we’d recalled first-term mayor Sheng Thao in November 2024 — but I’m still seeing election billboards all over town.

And by “billboards” I mean this particular billboard, in multiples. I shake my head every time I see it. What were they thinking?

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Billboard with a photo of former Congresswoman Barbara Lee. The text above her head reads We’re voting NO on the recall of Mayor Sheng Thao. The text on the left side reads Barbara Lee: Wrong then. Wrong now. Vote for Loren Taylor on April 15.
What is this ad saying? Photo: Nancy Friedman

Maybe you’ve already spotted the problems here, but I’ll break them down anyway:

  1. Three names. The most prominent, because they’re at the top, are those of Barbara Lee and Mayor Sheng Thao. Down below is Loren Taylor’s name. Who paid for the ad? Who are we supposed to vote for?
  2. One prominent face. Whoever paid for the ad evidently assumed that we know that the smiling woman is candidate Barbara Lee, who served from 1998 to 2025 as a U.S. congresswoman from California. (I’ll bet that many passers-by didn’t recognize her.) There are some ghostly faces behind her, of whom I recognized only former Mayor Jean Quan, over on the right. They’re smiling, too. Lots of happy people! I’m supposed to vote for the smiling lady in the foreground, right?
  3. A red herring. Why is “We’re voting NO on the recall of Mayor Sheng Thao” up there? The recall election — which had a messy and ongoing backstory

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Nancy Friedman
Nancy Friedman

Written by Nancy Friedman

Writer, name developer, brand consultant, idea-ist, ex-journalist. @fritinancy on Mastodon, Instagram, Bluesky, Threads, and elsewhere.