Cities are second nature to Donald Trump, who made his fortune, built his name, and sharpened both his style and his elbows in the glittering shark tank of New York business and society.

But as Trump arrives in Cleveland to claim the Republican Party’s presidential nomination, he inherits a party that has been almost completely routed from urban America—and has increasingly defined itself in opposition to cosmopolitan values. In most states, the GOP has established a commanding advantage up and down the ballot in the areas outside of the urban centers. But the Republicans converging this weekend on Cleveland can’t capture the biggest prize—the White House—without cracking the largest cities and inner suburbs.

The Republican choice to gather in Cleveland at all testifies to their challenge. Since 2000, no Republican presidential nominee has carried more than one-third of the vote in Cuyahoga County, which centers on the city.

Ordinarily a party might hesitate about convening so deep in the other side’s terrain. But Republicans now have a foothold in very few cities large enough to host a convention. Not long ago, reform-oriented Republicans with business pedigrees won mayoral races in New York (Michael Bloomberg) and Los Angeles (Richard Riordan). Now the Ballotpedia website reports that Republicans hold the mayoral office in just three of the nation’s 26 largest cities, and 13 of the top 50. The largest cities with Republican mayors are San Diego and Jacksonville; after that, the list quickly descends to Ft. Worth, Oklahoma City, Albuquerque, and Fresno.

In presidential politics, the GOP has lost even more ground in metropolitan America. Research by Drew DeSilver, a senior writer at the Pew Research Center, quantifies the retreat. In 1976, DeSilver calculates, Democrat Jimmy Carter won 57 and Republican President Gerald Ford 43 of the nation’s 100 most populous counties. In 2000, Al Gore carried 71 of the top 100 counties and George W. Bush 29. By 2012, President Obama beat Mitt Romney in 46 of the 50 largest counties, and 86 of the top 100.

The Democratic dominance of cities and their close suburbs has provided them a compounding return in votes, DeSilver’s research shows. In 1976, Carter won 51.3 percent of the vote in the 100 largest counties, enough for a roughly 1.6 million-vote edge over Ford. In 2000, Gore pushed that advantage to almost 57 percent, and a nearly 6.8 million-vote lead over George W. Bush. In 2012, Obama reached 61 percent across the 100 biggest counties, enough for a resounding 11.9 million-vote lead.

Romney won over three-fourths of U.S. counties; Obama in fact, captured fewer counties than Michael Dukakis did in 1988. Yet Obama’s commanding advantage in the biggest places carried him to a comfortable win. Just those 100 counties provided nearly half of the president’s votes.

This trend’s flip side is the GOP’s consolidating control over non-urban areas, not only in presidential races, but also in contests for Congress and state offices. The blue-dog congressional Democrats who once represented blue-collar rural districts are nearly extinct; rural and exurban strength also keys the lopsided Republican advantage in state legislatures.

This alignment reflects the shifting fulcrum of American politics. As the parties increasingly divide more along lines of culture than class, Democrats now rely on a socially-liberal coalition of minorities, Millennials, and secular, single, and college-educated whites drawn to the diversity and unruliness of city life; Republicans mobilize a competing coalition of older, religious, and blue-collar white voters, who mostly prefer more homogenous communities beyond the urban core.

These contrasts may prove especially stark this year. Mitchell Moss, a New York University professor of urban policy, notes successful Republican mayoral candidates, like Bloomberg or Riordan, have run as “management types—progressive socially and conservative on fiscal matters.”

But Trump’s political profile more resembles the white backlash mayors from the 1960s and 1970s—like Sam Yorty in Los Angeles or Frank Rizzo in Philadelphia—who swept to power promising to restore order (and implicitly to restrain minorities) amid the turmoil of rising crime and racial disturbances. Even as Trump expressed some concern about police shootings of African Americans this week, he echoed those predecessors by declaring himself “the law and order candidate” and sharply criticizing the Black Lives Matter movement.

The difference is that the working-class whites who formed the Rizzo generation’s political base are much less prevalent now in cities (and the electorate overall). Trump may amass huge margins in places beyond the metropolitan centers, where the sense of cultural and economic loss that he summons is felt most acutely. But he will still face daunting math if Hillary Clinton can maintain, much less extend, Obama’s advantage among the minority and white-collar white voters who increasingly drive urban politics.

Clinton seems acutely aware of the opportunity—and necessity—to perform well in cities. She’s showered them with targeted policies, from expanded pre-school to tax credits for investment in struggling neighborhoods. Apart from general promises to support law enforcement and create jobs, Trump has spoken little about cities; asked to describe Trump’s urban agenda, the incoming (Republican) president of the U.S. Conference of Mayors recently said, “I don’t have a clue.”

No GOP nominee since at least Wendell Willkie—and maybe Theodore Roosevelt—has deeper urban roots than the Queens-born Trump, who sometimes seems like a big-city tabloid incarnated. In business, Trump has shouldered his way into real estate markets from New York and Chicago to Washington, D.C. But unless he breaks the Democrats’ political hold on metropolitan America, he probably won’t get any closer to the White House than the hotel he’s building down the street.