Margaret Sullivan, the media columnist for The Washington Post, formerly the public editor of The New York Times, wrote a piece back in March of 2018 which is newly relevant today (excerpts):

“The idea that we can be saved through billionaire whims is truly incredible,” says the author, Anand Giridharadas, former New York Times foreign correspondent, who has spent the last several years researching a book that will be published in late August, “Winners Take All: The Elite Charade of Changing the World.”


Giridharadas [gave me] something of a sneak preview of the book, which began in concept when he became a fellow at the Aspen Institute.

Then, brainstorming with people from hedge funds, Goldman Sachs, Facebook and other corporations, it dawned on him that they had no incentive to accomplish their assigned mission: To formulate ideas that would change society for the better — to go from monetary success to “significance.”

It turns out, Giridharadas said, that the seductive notion of changing the world is “a powerful tool for keeping things exactly the way they are.” At most, the rich and powerful might concoct some small-scale charitable effort that makes little difference — he calls this “the side hustle of virtue.”

The basics stay the same, by design: Progress continues to benefit the privileged far more than those who truly need the help. The status quo “siphons the gains from progress to the top.” Growing wealth inequality is just one measure of that.

And yet we want to believe in what Giridharadas calls “the billionaire-savior delusion.”

This idea is so foundational in our society, so entrenched, that it cuts across our deepest political divisions.

“At the heart of the fantasy,” Giridharadas said, “is the idea that the world is best changed privately, on high, from the rich and powerful, not democratically, through political reform.”

On the right, it produces a President Trump, whom sufficient swaths of the country viewed as so rich as to be incorruptible: He couldn’t be bought, the thinking went, because a guy like that doesn’t need the money.

Grifter Trump pulled off the greatest con job in the history of the world. How did that work out for you?

Earlier this year, the media was all gaga with fawning media coverage of billionaire Starbucks CEO Howard Schultz, whose “independent” vanity campaign flamed out by September.

More recently, billionaire financier Tom Steyer joined the 2020 presidential race in the Democratic Primary. Democrats irked as billionaire Steyer joins 2020 race. “Critics on the left accuse Steyer, a liberal activist from California, of mounting a vanity project that they say has no real chance of success.”

And every four years, like clockwork, we get this announcement from the media’s favorite billionaire: Billionaire and ex-New York City mayor Michael Bloomberg is taking steps to run for president:

Former New York mayor Michael Bloomberg is making plans to enter the Democratic presidential primary campaign this week, a reflection of anxiety among party elites about the unsettled field of current contenders.

Bloomberg, who as one of the world’s richest men would bring significant financial resources to his own campaign but also inflame the populist wing of the party[.]

The move marks a major reversal for Bloomberg, who announced in March that he would not run for president, and also serves as a public rebuke of the performance so far of former vice president Joe Biden, who has attempted to build a coalition of the same moderate Democrats that Bloomberg would court.

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Bloomberg, 77, has been outspoken in his opposition to Warren’s and Sanders’s intentions to raise taxes on the extremely wealthy like himself, and on Thursday they returned the ill sentiments.
“The billionaire class is scared and they should be scared,” Sanders wrote on Twitter after news of Bloomberg’s possible entry became public.

“Welcome to the race, @MikeBloomberg!” Warren tweeted, providing a link to the impacts her policies would have on billionaires. She also sent out a fundraising email saying “the wealthy and well connected are scared.”

It is still possible that Bloomberg would not ultimately enter the race, but he is taking steps to ensure he will be on the ballot. Alabama’s deadline is Friday, and New Hampshire’s is Nov. 15.

Four years ago, Bloomberg flirted with an “independent” vanity campaign and spent a ton of money in preparation before, once again, announcing that he will not run.  John Cassidy said at the time, A Bloomberg Presidential Bid Was Always a Pipe Dream (excerpt):

According to the New York Times’s story on his decision not to run, the former mayor’s staff had “covertly assembled several dozen strategists and staff members, conducted polling in 22 states, drafted a website, produced television ads and set up campaign offices in Texas and North Carolina.”

All of this costly effort ultimately informed Bloomberg of what anybody with an ounce of political nous could have told him for free … Bloomberg had virtually no chance of becoming President.

As Philip Bump of The Washington Post snarks today, “Honestly, we should be kicking ourselves. Of course former New York mayor Michael Bloomberg is now, once again, flirting with entering the 2020 Democratic presidential nominating contest.” Just when you thought he was out, Mike Bloomberg pulls himself back in:

After all, there has been at least some form of Bloomberg-is-running static for each of the past three contests. In 2007, while he was mayor and during his last few months as a Republican, he talked to possible supporters about a 2008 run. In 2010, now an independent, his allies were at it again, trying to figure out how to make 2012 happen. In 2016, Bloomberg used a possible presidential run as a cudgel: If the race came down to Donald Trump against Sen. Bernie Sanders (I-Vt.), he would have no choice but to weigh in as a sensible alternative. In March of that year, he figured Hillary Clinton was good enough and decided againstrunning.

Bloomberg’s spasmodic discussions about running for president are so well-established by now that this is the second time we’ve been through this in this cycle alone. Seven months ago, he said he wouldn’t run, and yet here we are.

But again, we should have predicted this happening now. Bloomberg is a billionaire, and the past few weeks have seen a flurry of other billionaires expressing public consternation about the rise of Sen. Elizabeth Warren (D-Mass.) in the polls. One wrote a long, sad-sack letter complaining about her policy proposals and rhetoric. On Wednesday, former Microsoft CEO Bill Gates crankily objected to Warren’s tax proposals, suggesting hyperbolically that he’d have to pay $100 billion in taxes — leaving him with only the equivalent of 110,000 years of the median annual household income to subsist on.

There are more esoteric factors at play, too. Bloomberg would be forgiven as well for assuming that if voters were looking for a self-made billionaire with a lot in the bank, he had a lot more to offer on both fronts than the guy in the Oval Office. (The Democrats have a billionaire in the race, Tom Steyer, but he’s not making much of a dent.) Heck, it’s even a boom market for media coverage for former New York mayors. How could he miss?

When Bloomberg was last toying with the idea of running in 2020 and before Steyer jumped in, we raised what seemed at the time like an obvious point: Why do these guys think that the candidate Democratic voters will find most appealing is a white, male plutocrat? We walked through all of the reasons to think that was precisely not what Democrats wanted, given that the party has grown sharply more liberal in recent years and given that the strong 2018 election for the party was powered by nonwhite candidates and women.

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Part of the motivation, certainly, is the self-confidence that comes with having earned more money than one could spend several generations of lifetimes. Some billionaires seem more willing to conflate net worth with personal worth than most people, in case you hadn’t read the news in the past few years.

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In June, the Associated Press and NORC asked Americans what qualities in a presidential candidate would make them most appealing. The factors that would generate the most excitement. Both overall and among Democrats, the most appealing quality was experience in elected office, which Bloomberg certainly has — although so do most of the other Democratic candidates. In both groups of respondents, three of the least exciting qualities were a candidate who is old (check), one who is white (check) and one who is a man (check).

Incidentally, our saying the 77-year-old Bloomberg is old isn’t our being rude to the former mayor. Bloomberg said that he was “a little bit too old” to run for president.

He said it 22 years ago, on CNN’s “Crossfire.”

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Democrats may say they aren’t really excited about an old white man as a candidate, but, if so, no one’s told the plurality of the electorate that supports former vice president Joe Biden. Biden has led the field for most of the year, suggesting that an older white guy might just make it after all.

Biden’s poll numbers are predicated heavily on his moderate positions and his support from black Democrats (two groups that overlap significantly). If Bloomberg’s going to make a dent, he’s going to have to eat into Biden’s dominance with that pool of voters.

Which is where Bloomberg’s sketchy history becomes important. It seems pretty unlikely that Bloomberg will peel away much of Biden’s support with black voters, given his advocacy for — and ongoing defense of — stop-and-frisk by New York City’s police department. That policy overwhelmingly targeted nonwhite residents of the city and had no apparent effect on the New York’s violent crime. It’s a policy that Trump has forcefully endorsed, which doesn’t suggest that it’s something Democratic voters will embrace.

There are also questions about Bloomberg’s history with women at his eponymous media company. When harassment allegations from multiple women arose 20 years ago, he called them “out-and-out extortion.” At another point, he claimed that he was being targeted because he was well-known. These assertions might also sound familiar.

I have certainly been wrong about the political chances of New York billionaires seeking federal office before. It’s just hard to see, in this specific case, how a late entry by Bloomberg makes a significant run at Biden. Throwing money at the race only buys you a few percentage points, at least the way Steyer’s throwing it. Battling Biden on his turf may, in fact, increase the odds that Warren is the nominee, given that it’s safe to assume Bloomberg voters will be coming from moderates currently in the field like Biden or South Bend, Ind., Mayor Pete Buttigieg.

Why do it? Bloomberg’s past success has probably given him a sense that he can accomplish unlikely things. He probably has some non-billionaire consultants in his proximity who are happy to help him spend a small fortune on a race, a small fortune that for Bloomberg is barely a blip. Why not do it, really, when you’ve got no shortage of self-confidence and dollars?

Jack Shafer at Politico addressed this phenomenon earlier this year. How the Presidency Became a Billionaire’s Ultimate Prize:

So why then are so many billionaires running for president in the 2020 cycle or shopping for the office? Faux billionaire Donald Trump is obviously in again. (He’s been running since he was elected the first time.) Michael Bloomberg and Starbucks mogul Howard Schultz have taxied their personal jets onto the runway. Fellow plutocrat Tom Steyer was flying in formation with them until early January when he bowed out after assessing his chances, although he’s still a player, having pledged $40 million just to impeach Trump. And don’t forget the coquettish billionaires who’ve visited Iowa or otherwise teased the press with the notice of a candidacy: Mark Cuban, Oprah Winfrey, Mark Zuckerberg, Sheryl Sandberg and Bob Iger. This is a bestiary of plutocrats so plentiful it would require Audubon to collect, paint and stuff them for inspection by a political taxonomist.

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The modern presidency appeals especially to today’s billionaires who have reached that end point at which additional wealth conveys no additional joy or increase in status. They want a larger stage from which to dispense their pet theories, underlings by the hundreds of thousands, and a whole new org chart to dominate. What else but the White House could give them all they crave? It’s a mistake, of course, as Trump has learned, because the checks and balances of the legislature and the courts prevent a billionaire president from dictating by whim.

Yet the illusion persists, and the appeal of the job increases. The billionaire candidate looks at Trump and says: He’s a venal moron with the vocabulary of the third-grader and the patience of a chihuahua and he convinced a sufficient number of voters to back him! Trump’s success has aroused the other billionaires’ natural competitiveness, making them think they can conjure an Electoral College miracle, too.

The other appeal of the presidency for the end-stage billionaire is that it lends to them a seriousness of purpose.

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Another reason the modern billionaire class entertains the idea of running is because a huge underemployed industrial class of consultants and advisers exists to encourage them.

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The downside of the billionaire primary is that in today’s climate, it can easily become a referendum on their wealth. Nobody is going to beat up on Bloomberg for exploiting the masses, because his business model was about exploiting the wealthy. But they will and have portrayed him as clueless, removed and too privileged to run as a Democrat.

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The billionaire pile-up of Trump vs. Bloomberg vs. Schultz in November 2020 would be the ultimate money-politics event. But will it really happen?

Not a chance. Bloomberg will announce that he is not running because he has no path to victory, just like in the past. Thankfully, this will be the last time.