Critics call Bloomberg’s ads attacking Trump “effective.” Here’s why they’re not.

Dennis Bailey
5 min readFeb 19, 2020

What never-Trumper doesn’t love former mayor Mike Bloomberg’s online ads trolling the president and making fun of him? Yes, they’re good for a laugh and yes they no doubt ruffle Trump’s wig. Democrats and never-Trumpers obviously delight in someone who hits Trump where it hurts, who does the whole jujitsu thing to turn Trump’s bullying against him. Yes, let’s all laugh.

But as effective political advertising, do Bloomberg’s ads work? Do they convince a single Trump-loving supporter to even consider voting for someone else? More important (at this stage of the game), do they help convince Democrats that Bloomberg should be their nominee over the crowded field of candidates?

No. And I say this as someone who’s developed my share of political ads, both good and bad, for numerous political campaigns.

Bloomberg is making the same mistake Hillary Clinton made in her failed campaign. Remember her TV ads highlighting Trump’s obscene, offensive, bullying behavior, suggesting that kids should be kept away from the TV whenever the despicable R-rated candidate appears? Yup, the ads reinforced everything that those of us who can’t stand Trump already knew: he’s insane, he’s a lout and unfit to be president.

But have the people who make these ads ever met or talked to a MAGA-hat wearing Trump supporter? Here’s the thing: Trump’s boorish behavior that turns most of us off is EXACTLY what appeals to Trump supporters. They love his tough talk. They love that he talks like them without the highly scripted talking points that pour out of the mouths of most buttoned-down robotic politicians. People rave about how cool and intelligent Mayor Pete is. Just wait until he gets on the debate stage with Trump (if he ever does). None of those skills will matter. Why? Well, put yourself back in high school. Remember? No one liked the A student. I mean, c’mon. If I was on a coast-to-coast airplane trip and Elizabeth Warren sat down beside me, I’d probably pretend I was asleep. If it was Trump, I’d order a cocktail and probably have a hell of a time.

When I saw those Clinton ads unspooling the worst of Trump’s diarrhea mouth, I thought it was more effective for Trump supporters than opponents. I pictured his followers pumping their fists, high-fiving every time the ad came on. “Yeah, alright! Someone is finally telling it like it is!” The MAGA deplorables remind me of the line from Blazing Saddles: “You’ve got to remember that these are just simple farmers. These are people of the land. The common clay of the new West. You know… morons.”

Bloomberg now appears to be doing the same thing as Clinton, highlighting Trump’s deplorable behavior thinking that gets him somewhere. Hey Mike, We’re with you. We know all about Trump’s clownish, crude behavior. But what I want to know is why should you be president?

The ads are like those famous “Got Milk?’ ads from years ago. Remember those? Everyone loved seeing celebrities with a milk mustache. The ads created buzz, won awards and were mimicked by a variety of marketers. But guess what? The ads failed to do what they were supposed to do: sell milk. Milk consumption has declined steadily for decades. (Yes, it’s not uncommon for ad folks to forget their purpose is to sell product, not win awards.)

Sure, all his ad spending has allowed Bloomberg to climb into contention in the Democratic presidential primary. But that’s more the result of the weak field of candidates combined with the almost breathless free media he’s getting in national news outlets. This week there were eight stories on the New York Times politics page about Bloomberg and zero about Buttigieg who is actually on the ballot in the next two primary states and is in first place in pledged delegates so far. Does that make sense?

Bloomberg and some of the other Democrats seem more willing to chide Trump on his weight than his record. But there is a better ad strategy, I believe, that would combine Trump’s distasteful antics with his lies and failures, that would bother him just as much and might actually convince some soft Trump supporters to reconsider.

Democrats need to go right at Trump’s strength — the state of the U.S. economy that Trump is claiming credit for. Remember when John Kerry was the Democratic candidate for president? He was a decorated war hero running against a candidate who evaded service in Vietnam by being a weekend warrior in the National Guard. Kerry was doing everything he could to emphasize his veteran status (remember his “Reporting for Duty” salute at the convention?). The conventional wisdom was that Republicans would surely avoid bringing up his war record lest it emphasize the stark contrast between the candidates. But the evil genius Karl Rove knew better and “Swiftboating” was born, which completely undermined one of Kerry’s key strengths and kept him on the defensive for the entire campaign, which he lost.

Democrats should take a lesson. Take the economic message away from Trump. Here’s how (free of charge):

  1. First, get your own marketing slogan and a blue hat: “Take Back America.” Take it back from the lying, corrupt, racist, misogynist president who has handed the economy to his rich cronies, who is an embarrassment on the world stage and is threatening our national security.
  2. Show how Trump has kept the economy afloat by doing what he does best: borrow money — in this case $3 trillion added to the national debt — with no intention of ever paying it back.
  3. Go to coal country and talk to (and film) the miners that Trump promised he’d put back to work but has all but abandoned.
  4. Talk to the hundreds of dairy farmers in Wisconsin who’ve lost their farms due to Trump’s misguided trade war (and a bailout that cost taxpayers more than the GM bailout under Obama).
  5. Highlight his promise to raise annual GDP growth to 3, 4 even 6%, when in reality it hasn’t ever hit 3% during his term. In other words there’s nothing Trump can point to that has improved the economy in any meaningful way over the one he inherited from Obama (just like he inherited his millions from his daddy and squandered it all on failed casinos, a fraudulent “university,” and four bankruptcies).
  6. Keep talking about Trump’s biggest pride and joy — the border wall. Remind people he’s stolen billions from the Department of Defense, threatening our security, making our troops less safe, to pay for it (not Mexico, like he promised) and he still hasn’t built much of anything where a barrier didn’t already exist. There’s still 1,300 miles (out of 1,900 miles) that have no barrier at all. And didn’t Trump say he was good at building things? Another lie.
  7. What about his promise of a “better, cheaper” health care plan? It’s been three years. Where is it? Or was the plan all along to throw millions of people off their health insurance and deny coverage for pre-existing conditions? If so, mission accomplished.
  8. And yes, the massive tax cuts that did nothing to rev the economy for more than a couple of months and only served to fatten the wallets of the wealthy.

In other words, Trump supporters, face it: you’ve been conned, snookered, suckered and shafted. As Bob Dylan said, “How does it feel?”

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