Why Donald Trump will obsess over Michael Bloomberg

Donald Trump has a very simple view on the world: The richer and more famous you are, the better.

Which is why the President is virtually certain to fixate on the likely presidential candidacy of former New York City Mayor Michael Bloomberg.

Bloomberg, the former three-term mayor of Trump’s native New York City, is both very rich and very famous. The media empire Bloomberg built has built has pushed his net worth to more $51 billion, making him the 8th richest person in America, according to Forbes. (Trump is 275th on that list, with an estimated net worth of $3.1 billion.) Bloomberg’s philanthropy and spending on political causes close to his heart (gun control, climate crisis, soda, himself) has made him a national figure of some renown.

All of which makes him a lot like Trump — except richer!

Bloomberg has leaned into the comparisons between himself and Trump. In his speech at the 2016 Democratic National Convention, he said this:

“Now, we’ve heard a lot of talk in this campaign about needing a leader who understands business. I couldn’t agree more. I’ve built a business and I didn’t start it with a million-dollar check from my father. Because of my success in the private sector, I had the chance to run America’s largest city for 12 years, governing in the wake of its greatest tragedy.”

Assuming Bloomberg ultimately runs — and I assume he will at this point — he will presumably do so on this sort of message: I’m a businessman, like the current president. I’m just more successful, more stable and much, much richer.

And if you think that message won’t get to Donald Trump, then you don’t know Trump very well. In fact, we already have ample evidence that Bloomberg gets under Trump’s skin.

“‘Little’ Michael Bloomberg, who never had the guts to run for president, knows nothing about me,” Trump tweeted in July 2016. “His last term as Mayor was a disaster!” Trump followed that tweet up with: “If Michael Bloomberg ran again for Mayor of New York, he wouldn’t get 10% of the vote – they would run him out of town!”

Asked about Bloomberg’s potential candidacy on Friday morning, Trump went off. “He became just a nothing. He is not going to do well,” said Trump of Bloomberg. “He doesn’t have the magic to do well. ‘Little Michael’ will spend a lot of money … he’s got some personal problems and other problems …There’s nobody I’d rather run against than ‘Little Michael’.”

Now, simply being able to troll Trump with his wealth won’t win Bloomberg the Democratic nomination. But, it can’t hurt! The more Trump pays attention to Bloomberg, the more he elevates the mayor in the eyes of Democrats — the thinking being: Hey, this guy really gets under Trump’s skin, and that’s good!

And, there is a potentially compelling general election argument that goes like this: You liked Donald Trump’s business background? Well, I have that too! But, I’ve been more successful and am far more competent than the current occupant of the White House.

But, to make that argument, Bloomberg has to make the general election, which is a longshot at the moment.

Whether his candidacy happens and then whether it takes off is a very uncertain. What’s more clear is that the very fact that Bloomberg is seriously considering the race will bother Trump in ways that other candidacies have not.