The news that Michael Bloomberg has filed paperwork to enter the race for the Democratic nomination for president probably shouldn't come as much of a surprise. For nearly 20 years, a fawning media has often tossed out Bloomberg's name as someone who should vie for the White House, strangely convinced that who Americans really want to elect is a socially-moderate, fiscally-conservative New York billionaire.

Bloomberg himself has often entertained the notion. By one estimate, he's considered running at least five separate times over the years. In 2016, Bloomberg toyed for a minute with getting into the race as an independent candidate before deciding against it. (He has switched parties multiple times through the years, bouncing his registration from Democratic to Republican to independent and back again, seemingly only for personal gain rather than out of political conviction. Sound familiar?) Even this year, Bloomberg has been in a will-he, won't-he dance for months now.

It's still not clear if he will. Bloomberg has only registered for the Democratic primary in two states so far. But if he does run, the media titan says he'll self-finance the whole thing. What's $500 million to win the presidency when you are worth more than $52 billion, after all?

Reportedly, Bloomberg's motivation to seek the Oval Office owes to his sense that moderate Joe Biden won't win the nomination and his fear that two left-wing candidates, Elizabeth Warren and Bernie Sanders, look most likely to emerge victorious.

Publicly, Bloomberg has couched his possible entry in his concern for ensuring Trump is defeated, although that hasn't moved him to pour millions into backing Biden, who polls still show as mostly likely to beat Trump. The reality may be that Bloomberg and his billionaire chums, like Amazon's Jeff Bezos (net worth $110 billion) who urged the former New York City mayor to run, are even more worried about what a president Warren or Sanders would mean for their tax bracket.

Bloomberg's candidacy likely won't get far. But the media's frothing over his possible campaign is particularly revealing. On MSNBC's Morning Joe, Willie Geist remarked that "nothing would make President Trump more angry" than all the news coverage that would note the $50 billion difference (or more) between their two fortunes, the sort of talk more suited for gossipy Upper East Side dinner parties than a news show pretending to offer insightful political analysis.

This country club commentary about Bloomberg takes place in a larger media context that grossly over-represents billionaires in the news cycle and allows them to over-influence political coverage. For weeks now, media outlets have churned out detailed investigations of how Sanders' or Warren's tax plan will impact a handful of billionaires. Mark Cuban, Bill Gates, and Leon Cooperman, to name a few, have enjoyed plenty of opportunity to voice their protestations. On CNBC, Cooperman (net worth $3.2 billion) blasted Warren as "disgraceful" before firing off a round of expletives at the senator.

In a different moment, we might imagine such commentary from the fat cats as unsolicited, if not outright condemned. But given how repeatedly reporters have scurried to get their reactions — just Google "billionaires" right now and marvel at all the news coverage they are getting — we're awash in a political reality that is being overdetermined, if not outright remade, by billionaires' perspectives. "Who better to ask," Leslie Stahl said before her extensive interview of JP Morgan Chase chairman and CEO Jamie Dimon (net worth $1.6 billion) on 60 Minutes the other night.

Perhaps just about anyone else.

That's not likely considering how cozy many of the New York media elite are with the captains of finance and industry. But given that Trump's most consequential legislative achievement has been his controversial tax plan that further lined the pockets of the wealthy while hurting the middle class — a result that even Mike Bloomberg's media company has acknowledged – they might at least ask different questions of billionaires than how Sanders or Warren's tax proposals will dent their massive fortunes.

Surely Bezos or Cuban or Lloyd Blankfein (net worth $1.1 billion) might be confronted on whether their outrage over a possible "wealth tax" should be better directed against a president who is shredding the Constitution and undermining the basic system of American democracy that helped make their great wealth possible? In any event, it's remarkable that a potential Warren presidency rather than the actual Trump atrocity has made so many billionaires finally speak out.

Most Americans probably won't worry too much over what a Warren presidency will cost the billionaire class. Still, it's telling that most of the billionaires haven't taken the time to actually figure it out for themselves either. In a recent sit down with the New York Times' Andrew Ross Sorkin — the same man who gave us the Showtime drama Billions, no less — Gates offered that he was happy to pay more taxes, but drew a limit. "You know, when you say I should pay $100 billion," Gates said to Ross Sorkin, "O.K., then I'm starting to do a little math about what I have left over. Sorry, I'm just kidding."

Gates hasn't done the math because he doesn't need to. Those who have estimate that Gates would only pay about $6 billion in the first year under Warren, leaving him with more than $100 billion in his coffers. That he's more ready with a bad joke than with real knowledge about what a Warren tax plan would cost him demonstrates exactly how seriously any of this should be taken. Middle-class Americans, of course, don't have the same luxury to not crunch the numbers when it comes to evaluating their political choices, nor can they be as blasé about how any tax policy would affect their wallets.

We could stand to hear far more from those Americans.

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