Former New York City Mayor Rudy Giuliani was back in the news earlier this month, endorsing Donald Trump — if not formally campaigning with him — in the Empire State’s presidential primary.

The mayor is always a reminder that even the Big Apple, which Trump rival Ted Cruz derided for its liberal “New York values,” has occasionally been willing to put a Republican in charge.

There was the socially liberal Giuliani from 1994 through 2007, and then Michael Bloomberg in 2002 — that is until he became an independent and started antagonizing conservatives with progressive paternalism like his doomed ban on large sodas.

Apostasies aside, both Giuliani and Bloomberg get credit for this: they contributed to a now-bygone era of GOP success in urban America. “In the year 2000, Republican mayors governed half of the country’s dozen largest cities by population,” Politico reported. “Some of the party’s most provocative leaders had come out of city hall, including New York’s Giuliani, Los Angeles Mayor Richard Riordan and Indianapolis Mayor Stephen Goldsmith.”

Yet one city that has never elected a Republican to the helm is the center of American politics itself — the nation’s capital, Washington, D.C.

Long known as “Chocolate City,” the District of Columbia has consistently chosen black Democrats since winning the right to pick its local leaders in the congressional Home Rule Act of 1973.

Carol Schwartz, formerly a Republican on the D.C. Council, did earn 42 percent of the vote in a mayoral race against the District’s Democratic icon Marion Barry, but that remains the party’s high-water mark. It was 1994.

Why exactly has the GOP fared so poorly while doing better in other cities? Experts told InsideSources that factors include dismal Republican registration, the party’s repellent national image and the District’s uniquely contentious relationship with the GOP on Capitol Hill. Equally troubling — and perhaps related — are struggles with basic organizing and candidate recruitment, seeing as the Republicans didn’t even have a nominee in the past two mayoral elections.

For the third most recent contest, in 2006, the Republican standard-bearer was so obscure, Slate published an Election Day column titled “The Invisible Candidate.” He lost by 83 percent.

‘A Soviet-style political environment’

The first challenge, clearly, is the raw numbers. Just six percent of registered voters in the capital are Republicans, and D.C. GOP executive director Patrick Mara said that’s always been a huge hurdle. The former D.C. State Board of Education member has seen first-hand the poison of his party’s brand with Washingtonians, after making several unsuccessful runs for office.

“That’s all people talked about the entire time — that you’re a Republican,” Mara said. “I’ve been spit on, but you just wipe it off and move on.”

It was harder to move on from near-constant interrogation on the campaign trail, often about issues of cultural conservatism that had nothing to do with D.C.

“I’d be on the Metro and people would be asking me about creationism,” he said. “Eventually I’d just give up and get right into it: I actually believe in evolution. I’m pro-choice.”

Mara thinks the burden of the national brand is a big part of why Republicans have only ever elected three of their own to the D.C. Council. (Some intra-party politics to note: he was the one who ousted Schwartz from the Council in a 2008 primary, and did so supported by her fellow lawmaker David Catania — a firebrand of District politics who initially won election on the GOP ticket but turned independent, just as Schwartz would later do.)

Support for Schwartz over the years was always in spite of her Republican affiliation, and never a credit to it, according to veteran D.C. journalist Harry Jaffe, now editor at large for Washingtonian.

Jaffe said voters liked her personally, but she never popularized her party or changed the underlying dynamic: “There is a single-party system in the District of Columbia, and if a candidate wins the Democratic primary, the general election is a formality. That was true in 1978 when Marion Barry was first elected mayor, and it’s true today.”

Which isn’t to say the Washingtonian editor is happy about it. Although he’s collaborated with at least two Democrats on their respective memoirs — former D.C. Schools Chancellor Michelle Rhee and former Arizona Rep. Gabrielle Giffords — Jaffe thinks a stronger GOP would be good for the District.

“I mean this from the bottom of my heart,” he said. “It saddens me to have to live in a Soviet-style political environment. It’s just un-American.”

He also rejected the idea that black voters, even in a historically black mecca like Washington, are forever wedded to Democrats.

“There are a lot of African-Americans in the District of Columbia who are very conservative people,” he said. “They are very socially conservative. They are for capital punishment. They demonstrated against gay marriage.”

What’s more, D.C. has successfully elected a black Republican Council member once, noted another seasoned observer of District politics, columnist Jonetta Rose Barras. She said the victory of Baptist minister Jerry Moore in 1974, following his appointment by President Richard Nixon in 1969, “diminishes the argument” that blacks won’t back the right Republican.

Still, the fact remains that both black men who won the GOP mayoral nomination — Arthur Fletcher in 1978 and Maurice Turner in 1990 — lost in landslides.

“African Americans are very closely associated with the Democratic Party,” said Catholic University politics professor Matthew Green. Prior to 2000, fully six in 10 D.C. residents were black, and seven in 10 before 1980.

The statehood wedge

Another key contemporary challenge, according to both Barras and Mara, is the politics of D.C.’s defining quest for statehood. Congressional Republicans are much more resistant than their Democratic counterparts to supporting the perennial proposal, which would add a new pair of senators and another voting representative in the House, all from a heavily Democratic jurisdiction.

GOP reluctance is completely understandable from a political perspective, but it certainly feeds the perception that Republicans are hostile to D.C.

It’s not great messaging for expanding a tiny tent, and Mara said local Democrats are quick to exploit this as a wedge issue.

“It’s the playbook,” he said. “Like you can use guns in West Virginia, you can use the Republican Congress here.”

That helps explain why the GOP didn’t benefit when statehood failed to advance in any significant way during the time Democrats were in control on Capitol Hill.

“I would say that both sides are dismissive of D.C., and that’s what people miss,” Mara said. “Until we start electing Republicans in D.C., it’s very unlikely we get statehood under almost any circumstance.”

No clear solutions

To escape this catch-22, though, the stars would need to align, Green said. At the mayoral level, “Ideally you’d have an African-American Republican who’s moderate on certain issues, who opposes Congress meddling in D.C. affairs, and the third thing on top of those would be a really weak Democratic candidate.”

When Mara talked about Giuliani’s success, he noted that the New Yorker benefited from unique outside forces, including anxiety about crime.

The mayor also had something no D.C. Republican has: assistance from a big state party.

“You can’t take New York City for granted if you hope to win at the top of the ticket with governor or Senate races, and you have to spend money there,” Mara said.

Despite being in Washington, national GOP leaders don’t invest in D.C. either, which leaves Jaffe baffled.

“Why hasn’t the RNC realized that a strong Republican Party in the nation’s capital could actually give them a local backdrop for whatever they want to put together at any given time?” he said.

It might be a persuasive argument, if there was anything for the RNC to build on.

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