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Bloomberg as Trump Truth-Teller

Nov. 08 2019

The news that media mogul and former NYC mayor Michael Bloomberg is likely to enter the presidential race set off a collective groan. Democrats, of course, want a self-funded billionaire in the race about as badly as they want Hillary Clinton to enter the 2020 fray. And media pundits, many of whom live in New York and saw their city transformed over Bloomberg’s 12-year reign (complete with surging costs of living) are wondering just how many wrenches Bloomberg can buy out of his $50-billion-plus fortune to throw into the works of the nomination process.

But perhaps everyone’s missing the point.

Bloomberg is positioned better than anyone to tell damaging stories about Donald Trump. No one in the race has more firsthand dirt on Donald. For 12 years as mayor, he saw every questionable real estate deal — and certainly plenty of other Trump shenanigans — up close. And let’s not forget, Bloomberg served as mayor just after Trump’s embattled personal attorney, Rudy Giuliani. How much damaging information does Bloomberg have on Rudy? Odds are, plenty.

That in mind, along with Bloomberg’s vast fortune and lack of name recognition between the coasts, could it be that storytelling is Bloomberg’s entire goal? That by entering the presidential race, Bloomberg instantly gives himself a platform to take shot after shot at Trump such that, even if he falls well short of the nomination, Bloomberg sets up the Democratic nominee to run against a heavily damaged Donald?

Being the Trump truth-teller was certainly current NYC mayor Bill de Blasio’s intended approach, but he didn’t have the street cred or war chest of Bloomberg. (On the latter, who does? Tom Steyer is impoverished by comparison.) Still, if damaging Donald at any cost to prevent a second term is indeed Bloomberg’s strategy, he’s the right person for the job. Not all the attacks may stick, but Bloomberg can afford to keep up the bombardment as long as he feels necessary, or until something does inflict serious damage. Of course, this approach comes with risk.

For one, Trump can attack Bloomberg for having run and served as a Republican to get on the mayoral ballot. Also, Bloomberg corralled the city council to throw the rules out the window so he could run for a third term — so it’s a bit hypocritical for Bloomberg to attack Trump for taking a wrecking ball to established norms. And even among his supporters, Bloomberg was a divisive mayor given the rate at which the wealth gap widened during his tenure. The city’s luxury high-rises had open doors for oligarchs, with the mayor himself practically rolling out the red carpet for them — and relegating longtime residents to the outer boroughs and beyond in the process.

But all that might pale in comparison to the stories Bloomberg can tell about Trump. That might be why, the morning after the news broke about Bloomberg entering the race, Trump responded with his usual approach: an insult, specifically that there’s no one he’d rather run against than “little Michael.” It was a measured first shot, because saying more now would only get Bloomberg talking.

And once Little Michael does start speaking openly (and opening his checkbook), Trump might not feel like Bloomberg is his preferred opponent. What’s more, the Democrats currently leading the pack might be wise to just sit back and let Bloomberg tell tales about Trump, as well as take the return fire, since that could be just the rich-New Yorker side skirmish that Elizabeth Warren, Bernie Sanders, Joe Biden or Pete Buttigieg could use as a springboard.

Calculating, strategic and every bit as media-savvy as Trump, this might even be an outcome Bloomberg’s contemplated — a martyrdom everyone on the left can get behind.