When The New York Times broke the story Saturday that former New York mayor and Rahm Emanuel buddy Michael Bloomberg is exploring a third-party run for president, my mind raced with implications of what his entry might mean to the strangest presidential race since Teddy Roosevelt ran on the Bull Moose ticket in 1912.

Unlike Chicago and Daley, New York Misses Bloomberg

By the time the multibillionaire Bloomberg turned the mayor’s office over to Bill de Blasio, there was strong feeling among New Yorkers that after three term (12 years) it was time for fresh leadership.

Describing de Blasio’s chilly outdoor inauguration on New Year’s Day 2014, I wrote at the time, “The three-termer sat glum-faced in a front-row seat as de Blasio’s invited speakers and other newly elected officials cast the former mayor as a plutocrat/villain.”

Predictably, de Blasio’s promise—he ran on the theme of a “Tale of Two Cities” and a pledge to tax the wealthy—collided with the difficulty of governing a large city. Nostalgia for Bloomberg—for the perceived safer and cleaner streets under his rule—has grown, especially in the wealthier, whiter parts of New York.

That's precisely the opposite of what occurred in Chicago.

When Rich Daley left office in 2011, the thick-tongued, bumbling six-termer (22 years) seemed irreplaceable, at least in the wealthier, whiter parts of Chicago. Local news outlets and city dwellers, even progressives who had no love for the machine and kept a tally of Daley cronies convicted of corruption, cast Richard J.’s son as unique, his steady hand pushing a gritty, rusting, outmoded industrial morass into the realm of glittering and global—all those trees and flowers and festivals, topped off by the gorgeous Millennium Park.

At Rahm’s inauguration on May 16, 2011, Daley was treated by the incoming mayor, an old Daley family friend, and by the audience watching in the park’s Pritzker Pavilion, with unabashed gratitude and respect. The Sun-Times celebrated Rich Daley in an editorial: “We have found that new sense of purpose, that larger vision … We grew up together, Rich Daley and the City of Chicago. The man shaped the city and the city shaped the man.”

But the rot in the city’s budget, privatization deals, public schools, and infrastructure, soon choked the city’s air with the stench of failure. Daley fell from celebrated and toasted to a cartoon of an inept leader: dumb, yes, but also canny enough to know he had passed a bag of crap to his successor and escaped to make money and deals around the world. Today, Rich Daley couldn’t be elected to a Local School Council.

Rich Like Rauner, But Similarities Don’t Go Much Further

Bloomberg apparently believes that he could be elected to almost any job, including the presidency. The Times reports that the multibillionaire is prepared to spend $1 billion of his reported $37 billion fortune on a campaign.

First up will be introducing himself to people who don’t live on the East Coast. A national poll this month showed that 43 percent of voters had either never heard of Bloomberg or held no opinion.

His aides promise a decision on whether he'll run by March—before or just after the March 15 Illinois primary. The plan is to flood the airwaves with commercials introducing the founder of the financial and media global behemoth Bloomberg L.P. to the American people.

In other words, Mike Bloomberg plans to take a stab at buying the election, just like another really rich guy, Bruce Rauner, who put $27.5 million of his own stash (about $700 million) into his campaign for governor.

Rauner stuffed the airwaves with “Shake Up Springfield” and “Bring Back Illinois” commercials, showing how a Republican with zero name recognition, who had never run for public office, could win a hotly contested primary and go on to win a general election against an incumbent governor in a blue state.

In an editorial endorsing Rauner in November 2014, the Sun-Times boosted the private equity mogul as a man who “could be the Michael Bloomberg of Illinois, fiercely free of political control, keeping his distance from the culture wars, achieving the kinds of economic wonders for our state that former Mayor Bloomberg achieved in New York City.” (Oops.)

Unlike Rauner, Bloomberg is a passionate advocate of abortion rights and of immigration reform. He told NBC's Meet the Press in 2011, “This is a country that became a superpower because of the immigrant population, and unless we continue to have immigrants, we cannot maintain as a superpower.”

And nobody is stronger on gun control than Bloomberg. He spread some $50 million of his money around the country to anti-gun candidates, including a $2.2 million outlay to Robin Kelly that bought her nonstop TV ads and, as a result, Jesse Jackson Jr.’s congressional seat.

An Independent Streak

Formerly a Democrat, Bloomberg ran for mayor of New York in 2001 as a Republican because he saw that switch as his best route to victory. In 2007, he became an independent.

A slight difference in party affiliation hasn’t put a damper on the friendship between Rahm and Bloomberg. They both portray themselves as pragmatic, results-oriented managers. Just as Wall Street loved Bloomberg and he loved it back, so LaSalle Street's love for Rahm is reciprocated. Rahm happily collects contributions from Republican business types in both the city and the swankiest suburbs. Stacks of it, for example, come from Ken Griffin, a Republican hedge-fund founder known as “the richest man in Illinois.” 

In October 2011, while still mayor, Bloomberg traveled to Chicago to appear on a Chicago Ideas Week mayors panel with Rahm and Atlanta mayor Kasim Reed. I noted that so simpatico were Rahm and Mike that “Bloomberg could be a key funder of a Rahm run for the presidency in 2016 or 2020.” But then Rahm’s national ambitions crashed on the shoals of the suppressed Laquan McDonald video, and the mayor tumbled from respected to reviled. A presidential run now seems far-fetched.

If Bloomberg were to become president, he would be the first mayor of a major city to ascend to the White House.  At that Chicago Ideas Week panel, Bloomberg said forcefully—and it seemed to me that he aimed the remark at Rahm—“Mayors don’t go on to be president.” But Donald Trump has already shown in this campaign that the old rules don't apply, and Bloomberg is obviously ready to follow suit when it comes to this rule of his own.