Democrats 2020

Bloomberg’s Relentless Trolling Is Getting to Trump

The president’s advisers have told him to ignore Bloomberg—but when the billionaire took his fight to Fox News, Trump had to speak out.

By Alison Durkee

January 23, 2020

Michael Bloomberg stands and waves his arm.

Since he made his late entrance into the Democratic presidential primary, former mayor Michael Bloomberg has had one singular goal: to relentlessly troll, and ultimately beat, President Donald Trump. Sure, Bloomberg seemingly wants to be actually be president, but the billionaire's campaign has so far largely directed its focus toward taking down the man in the White House, rather than any of Bloomberg's Democratic rivals. From buying a $10 million Super Bowl ad solely to get “under Trump’s skin” to pledging his riches and vast political ground game to whomever the Democratic nominee ends up being, Bloomberg’s campaign has been clear that its primary aim is to stick it to Trump—and apparently, the plan is working.

The New York Times reports that despite Bloomberg's relatively low status in the polls—he's currently averaging around seven percent, far below frontrunners like Joe Biden, Bernie Sanders, and Elizabeth Warren—the former mayor is successfully getting under Trump's skin. Despite repeated urgings from his advisers to ignore Bloomberg, Trump has apparently been “pricked” by Bloomberg's massive ad buys, which have plastered the billionaire and his anti-Trump messaging all over broadcasts of the Senate impeachment trial and Trump's usual media diet of Fox News. The president was reportedly rankled by one ad in particular, which aired on Fox & Friends and targeted Trump's treatment of military leaders. Bloomberg campaign manager Kevin Sheekey even made an appearance on the show to introduce the ad, emphasizing that Trump “weakens the country by attacking [the military].” So naturally Trump, who's reportedly concerned about losing support among Americans in uniform, turned to Twitter to air his grievances. “Mini Mike Bloomberg is playing poker with his foolhardy and unsuspecting Democrat rivals,” Trump tweeted Wednesday in response to the ad, pointing to Bloomberg's pledge to financially support the eventual Democratic nominee. “The fact is, when Mini losses, he will be spending very little of his money on these ‘clowns’ because he will consider himself to be the biggest clown of them all—and he will be right!” (The Trump campaign has insisted that it's not worried about Bloomberg's candidacy, with campaign spokesman Tim Murtaugh telling the Times, “It’s a free country and he can set his money on fire if he wants to.”)

Trump's distress over Bloomberg seemingly stems from the president's own insecurities in comparison to the former mayor, a successful billionaire businessman who's achieved the kind of unabashed financial success that Trump—whose business has filed for bankruptcy six times—so badly desires. “Trump fears Bloomberg because Bloomberg is actually the guy who Trump played on TV—a fantastically wealthy, self-made success with unlimited resources and a willingness to spend it,” former Obama senior adviser David Axelrod told the Times. But the relationship also goes both ways: Bloomberg has largely been able to aggravate Trump, Axios noted Wednesday, by running a campaign that openly covets the Trump campaign's success. The Bloomberg campaign is specifically modeling itself after Trump's campaign and attempting to replicate its successful elements, from its mammoth Facebook ad buys and media ubiquity, to trying to make “Mike Will Get It Done” the next “Make America Great Again.”

How well Bloomberg's strategies will work out for his own candidacy remains to be seen—after all, Bloomberg still hasn't cracked the top tier of candidates even after throwing gobs of money at the race, spending more than $256 million on advertising in less than two months. (And as the Times points out, the ads always tout Bloomberg's own successes even as they go after Trump.) But Bloomberg's status as the Democratic field's resident Trump troll could be helpful for Democrats nonetheless. The Times notes that some Democratic observers are “relie[ved]” by Bloomberg's ability to annoy Trump as other candidates cannot, and as rival Democratic candidates spar with each other or emphasize policy messaging over Trump attacks, Bloomberg's overt focus on antagonizing the president could fill a useful void. Bloomberg's vast resources have allowed him to bombard both battleground states and Trump strongholds alike with anti-Trump messaging now known to trigger the president—which could endure even if his candidacy does not. “While the other Democrats are fighting and sniping with one another in Iowa, we are running a nationwide campaign that is taking the fight directly to President Trump on issues where he is extremely vulnerable,” Bloomberg adviser Howard Wolfson told the Times.