The bizarre circle of Donald Trump, Rudy Giuliani and Mike Bloomberg

Just when it seemed as if our Twilight Zone politics had reached the limits of weird, we now have former New York City Mayor Michael Bloomberg gearing up to run for president against former New York City real estate tycoon Donald Trump, who may be impeached in part because of the many activities of former New York City Mayor Rudolph Giuliani.

There is a colorful backstory here. It involves New York politics, where relationships, like rush hour traffic in Manhattan, veer and sometimes collide. The three have always been New York City fixtures. They have rubbed elbows. They have been ubiquitous at events where ribbons are cut and black ties donned. They have also bumped into each other on the way in and out of parties, not the cocktail kind but the political kind.

Giuliani began as a Democrat, then switched to an independent in the 1970s, then became a Republican in the 1980s. Bloomberg also began as a Democrat, then became a Republican in the 2000s, then switched to an independent for more than a decade. He returned as a Democrat for the 2018 midterms, where he spent $80 million supporting party candidates. Trump was a Republican in 1987, an independent in 1999, a Democrat in 2001, a Republican in 2009, an independent in 2011, and a Republican in 2012. But through it all, Donald was die hard about, well, Donald.

Both Trump and Giuliani shuffled their ideologies like cards in a casino, but give Bloomberg credit. He may have switched parties, but Bloomberg never discarded his principles on key issues like gun safety and climate change. Still, the three New Yorkers do share a proficiency in tactical street smarts, honed at about the same time and in the same place. Even before Trump, Giuliani produced reality television moments to beef up his image. As United States attorney, he timed arrest announcements to break on the evening news, according to the New York Times.

The Village Voice wrote that Giuliani once listed for reporters the officials he was likely to indict. In 1986, he and then Senator Alfonse D’Amato posed for one the most awkward photo opportunities in history, dressing up as undercover drug buyers. A fashion review by Slate said that his “casual Friday trousers and gold belt buckle made him look more like a man who wants to sell homeowners insurance than a drug addict” and his “post cataract surgery glasses aren’t very menacing either.”

Giuliani preceded Trump in inciting live wire crowds. “Rudy’s Racist Rants” is how the Cato Institute, not exactly a megaphone for liberals, described his behavior during a 1992 riot of off duty cops against David Dinkins, the incumbent African American mayor at the time. Giuliani infamously egged on police as they stormed City Hall, many hurling racial epithets. Giuliani beat Dinkins in 1993. But as he neared the end of his second term in 2001, he was widely unpopular. It looked as if Democratic candidate Mark Green was going to wallop the Republican candidate, Bloomberg.

Then, two months before the election, terrorists struck the World Trade Center. Even critics of Giuliani recognized his leadership in lifting the city from the smoke and rubble. In fact, one New York politician compared his response to that of Republican Governor George Pataki. “There was one leader for 9/11. It was Rudy Giuliani. If it defined George Pataki, it defined George Pataki as not being the leader. He stood behind the leader. He held the leader’s coat. He was a great assistant to the leader. But he was not a leader.” The politician who said that was Andrew Cuomo.

Giuliani subsequently rebounded in popularity, and his endorsement of Bloomberg assisted that Republican victory. Before the endorsement, Bloomberg was 16 points behind Green. On election night, Bloomberg won, 50 percent to 47 percent. But there was a political wrinkle. In the aftermath of 9/11, some Giuliani supporters floated the idea of postponing the inauguration of Bloomberg for the sake of continuity. The proposal was quashed, but Giuliani embraced it, irking Bloomberg supporters.

The three have been bound by proximity, ambition, and the unique style of New York competitiveness you see in the Citi Field stands when the Mets play the Phillies. They also share another characteristic of challenging electoral norms. In 2008, Bloomberg convinced the New York City Council to extend term limits so that he could run again. Today, Trump disregards presidential standards in pursuit of whatever cravenness excites him at the moment. Giuliani has gone from federal prosecutor who upheld the rules to feral defender of a president who stomps on them.

They all share quintessential New York chutzpah. It is an unnerving bravado, a belief that that one can accomplish what others cannot. On that, they are cut from the same cloth. If Trump and Bloomberg end up facing each other on a debate stage, it should be set to the score of the Frank Sinatra classic, “If I can make it there, I’ll make it anywhere. It’s up to you, New York, New York!” But first, Bloomberg must make it past Iowa, New Hampshire, and South Carolina. Meanwhile, Trump must worry about Arizona, Wisconsin, and Pennsylvania. Giuliani? His heart is in Kyiv.

Steve Israel represented New York in Congress for 16 years and served as the chairman of the Democratic Congressional Campaign Committee from 2011 to 2015. He is now the director of the Institute of Politics and Global Affairs at Cornell University. You can find him on Twitter @RepSteveIsrael.