In October of 1993, a young liberal senator of the Massachusetts General Court launched a campaign to dethrone the chamber’s president, who had first been elected to the office in 1978. It was time, said Norfolk upstart William Keating, to clear the air in the statehouse. The old guard, Keating claimed, was rotten and out of touch; a new generation was ready—and entitled—to take the reins from the last survivors of Boston’s bygone era of machine politicians.

Billy Bulger was his white whale. A South Boston native, the Senate president had first been elected to the General Court in 1960. Inconveniently for Keating, Bulger was famously resistant to the kind of corruption and underhanded dealing that most people objected to in old-school city politics. But he was a savvy politician, and he ran a tight ship in the Senate. What’s more, he was a socially conservative populist in the old Boston Democrat mode; his challenger sat in the center on markets and firmly to the left on social issues. There was little room for Bill Keating to move upward in a Senate still led by Billy Bulger. It didn’t help that Bulger thought very little of Keating’s mental abilities, and didn’t do very much to hide the fact.

Keating’s coup might have benefited from a little bit of caution. The state and its representatives were getting more liberal, and he might have found some backing on the merits, especially if he had waited a few more years. But he reached immediately for a scorched-earth policy, advised by a well-paid consultant with a bone to pick with Bulger. When he announced his intention to challenge the president, Keating promised to wage an offensive campaign inside the district of any senator who refused to back him.

That crossed a line not just for Bulger—whose support was unshakeable in the neighborhood where he’d lived since childhood—but for plenty of senators as protective of their districts as of their seats themselves. Though times were changing rapidly, many elected representatives still thought of themselves as meant to represent the people who elected them. A senator’s relationship with his constituency was sacrosanct, and it ran both ways. Bill Keating had no business in Bill Bulger’s district, or in anyone else’s. This was an era when Bostonian wisdom still held: all politics was local.

The photo pages of Bulger’s memoir include a half-page snapshot of a “Beat Bulger” rally at Faneuil Hall in Boston, Keating at the podium behind a massive banner, identified as “the leader of what he perceived as a Senate rebellion.”

When the primary rolled around in September of ’94, Keating’s entire effort was demolished in what the Boston Herald called “an awesome display of political muscle.” He had started the campaign with six out of 31 Democratic senators on his side, hopeful that the election would boost him to 19; he ended it with five.

Twenty-eight years later, and now it’s Bill Keating who looks untouchable. When January rolls around, Bulger’s thwarted liberal challenger will begin his seventh term in the U.S. House of Representatives.

He won reelection last month by nearly 19 points, in the only district in the state where Joe Biden failed to break 60 percent. Three of the four Massachusetts counties in which Hillary Clinton performed worst in 2016—Plymouth, Bristol, and Barnstable—cover the bulk of Keating’s district; but the congressman won reelection that year by more than 22 points.

The district’s electoral history only gets more interesting the further back you look. Barnstable County is the largest county wholly contained in MA-9, with just under a third of the district’s citizens. From the foundation of the GOP in 1856 to the election of Bill Clinton in 1992, Barnstable voted for the Democrat for president exactly once: against Barry Goldwater in 1964. Even Hyannisport’s own Jack Kennedy could not swing the county four years before. Plymouth, Nantucket, and Dukes all went for Nixon in ’60 as well, not to mention ’72. (The only other county to do so either time was sparsely populated Franklin, up in the Pioneer Valley.)

In that nearly century and a half, the only other time Barnstable turned against the Republican nominee was in 1912, when—along with only Plymouth, Dukes, and Keating’s native Norfolk—it swung for Theodore Roosevelt’s doomed Bull Moose campaign.

The wild card is Bristol County, which actually went blue before most of the state. But it matters when it went blue, and why. The two largest municipalities in Bristol County are Fall River (partly in MA-9) and New Bedford (entirely in the district). Both grew up over the course of the 19th century as centers of commerce and industry. By 1857, buoyed by the whaling industry, New Bedford was the richest city per capita in the world.

By the first decades of the next century, not just the collapse of whaling but the failure of established Massachusetts mills to compete with new, low-wage (and thus low-cost) competitors had turned the cities’ fortunes. In an astonishing 29-point swing from just the previous election, Bristol flipped for Al Smith in 1928. How the Catholic governor of New York beat proto-libertarian Herbert Hoover in a county defined by already-struggling industrial towns and their Catholic working classes is not difficult to parse.

The obvious should be granted: these are old numbers, and the demographics of, say, Nantucket have changed quite a bit since 1912, and even since 1972. It’s safe to say that, barring an act of God, Martha’s Vineyard will not be voting for the next Richard Nixon for president. But the history of one of the longest-inhabited pieces of land in these United States does endure—or, at least, it echoes—in ways that could be leveraged by a shrewd campaign.

Huge portions of Bristol and Barnstable Counties are still composed of Portuguese and Irish Catholics: socially conservative populists who will vote reliably against abortion and for robust economic policies, if anyone gives them the option to combine them. Many of Plymouth County’s most reliable voters are still old-school Yankee Republicans, with the party’s historic attachment to domestic free markets and its openness to tariffs, but without its recent conflation of the former with libertarianism—more Calvin Coolidge than Charlie Baker.

Every two years, Bill Keating wallops his opponent in what should be the only competitive district in the state. It is easy to imagine a candidate who might knock the congressman off his high horse: one who unites the currents of the New England political tradition that ran against Hoover in 1928 with those that ran for Roosevelt in 1912; those that ran in Richard Nixon’s favor in three different elections with those that drowned Barry Goldwater in one; those that gave Reagan a deep-red victory in Plymouth County in 1984 with those that have kept Bristol blue since 56 years before that.

It seems unlikely that the Massachusetts GOP has considered any of this in 2022, or in any other election cycle since Barnstable flipped three decades ago. For last month’s election, the party’s nominee to challenge Keating was West Bridgewater native Jesse Brown, a Marine veteran appointed by Governor Baker to a minor economic advisory board.

Brown, a gangly self-made businessman with less charisma than John Kasich, was already at a disadvantage. The region’s Republican voters have long shown a preference for rock-em-sock-em candidates with strong personal charm, from Teddy Roosevelt through Richard Nixon right up to Donald Trump. They have never come to the polls for skinny dorks, from Woodrow Wilson to Barry Goldwater to George H.W. Bush.

Even starting from behind, Brown did himself no favors by hedging every bet.

With his only political credential tied to the state’s liberal governor, Brown was smart enough not to hype up the relationship. (Baker’s supposed popularity is immensely overblown. Liberal Republican governors in blue states overperform in approval polling because enough Democrats support them in substance—and enjoy the feeling of control over GOP leaders—and enough Republicans figure they’re the best they’re going to get. The 74 percent approval rating obscures the fact that Baker wouldn’t even be competitive in a Massachusetts presidential primary in 2024.) But neither did the nominee dare to criticize Baker, or offer any alternative vision.

In a cycle when GOP voters were highly motivated by culture war concerns, Brown stayed out of the fight completely. Of eleven “On the Issues” tabs on Brown’s campaign website, not a single one pertained to any of the major social issues of concern to Republican voters—not abortion, not the family. No trace of religion can be found anywhere in the erstwhile candidate’s persona.

After six years of strong indication that populism is a winning message for Republican candidates, Brown offered nothing but boilerplate campaign messaging about “restor[ing] fiscal sanity” and “reducing regulatory barriers.”

In fact, it is hard to find a single issue on which Brown took a meaningful stance. And it’s hard to find a method, or a town, or a voter bloc in which Brown seriously campaigned. The simplest explanation as to why Keating keeps winning so big in a D+4 district is that nobody really seems to be trying to beat him.

Jim Lyons, who as chairman of the Massachusetts Republican Party is ostensibly pulling strings, points toward different problems. Lyons has been widely criticized in his tenure as party chairman, beginning in 2019, as a Trump-aligned radical in the state of Charlie Baker. But while Lyons has moved toward Trump in recent years, it’s worth remembering that he served in 2016 as the state chair for Ted Cruz’s primary campaign. If not his loyalties, at least his instincts lie elsewhere.

This has been clearest on economics, where the MassGOP has maintained its Cruzite market liberalism through every grassroots wave of MAGA populism. And while Lyons, a noted pro-lifer, has tried to pull the party rightward on social issues, he has been almost entirely unsuccessful—due largely to opposition from the Baker-aligned left wing.

Geoff Diehl, the roundly defeated Republican nominee for governor this cycle, misread the situation similarly. Though aligned with President Trump from the beginning, Diehl has little more clarity than Lyons on the issues. Like Lyons, he has tried to replicate Trump’s magic without replicating his platform. When he echoed the president on substance at all, it was almost exclusively on immigration, even as a mere 7 percent of Massachusetts voters ranked the issue as the most important heading into the election.

To their credit, both Lyons and Diehl seem to recognize that Trump’s win was significant—that his shattering of the old Republican orthodoxies could point to a viable long-term strategy. Yet neither man seems to understand exactly why or how.

Immigration, as suggested, is a prime example of how these Republicans miss the mark. Diehl made it a linchpin of his miserable campaign, hoping that the issue that motivated Trump’s base might deliver Massachusetts in the midterms. But immigration is not a live issue in Massachusetts the way it is in many red states for at least three obvious reasons.

First, many Massachusetts immigrant communities—especially in the southeastern portion of the state that makes up the 9th district—are centuries old and well established. The Portuguese population of the region, for instance, has been there since the founding of the country, drawn in by the whaling and fishing industries. It has proved remarkably able to absorb new arrivals—not just from Portugal, but from other Portuguese-speaking points of origin like Brazil and Cabo Verde. The problem of assimilation that plagues other areas is nearly rendered moot here.

The second reason is economic. Massachusetts has a slightly lower than average unemployment rate and its economy is not substantially composed of any of the major industries, such as farming, where American workers’ wages are routinely undercut by illegal competition in other states, if the jobs aren’t taken off the market altogether. The high-skilled urban voters who do compete with a different kind of immigrant in Massachusetts are largely voting Democrat either way, and thus have little bearing on Republican electoral strategy.

Third is simple geography. In the age of air travel and visa overstays, every state is a border state in some sense. But in another sense, it’s still true that only border states are border states. The world is getting smaller, but Massachusetts is still a small piece of territory 2,000 miles away from the country’s southern border. There are no invasions here of the kind or scale experienced in states like Texas, Florida, and Arizona.

Immigration is out of control in this country, yes. But it is not top-of-mind for most Massachusetts voters, and it is not going to win any elections in the Bay State.

In a Massachusetts election, the most important issue is always going to be the economy. This is all the more true in an age when Biden’s Democrats have made life unaffordable for a vast majority of Americans. Center-right populism of the kind embraced by the Trump wing of the GOP in recent years offers an alternative to the left’s high-cost, low-reward strategy that could unite both the working-class Democrat and the middle-class Republican blocs of the 9th district.

These two groups can also be brought together along social lines. Vast swaths of Catholics in Eastern Massachusetts still vote Democrat out of habit. A pro-life candidate with the right economic messaging could peel them away in droves from the party of abortion radicalism. The right to life, along with other common-ground priorities like crime reduction and education, could help alleviate any economic tensions between the camps.

Since at least 2016, a realigning election has been inevitable. New coalitions have been slow to form, and much-anticipated shifts have turned out to be less than tectonic. But the status quo is still unsustainable, and if the first domino falls in Massachusetts—where it is certainly least expected—the nationwide repercussions could be immense.

Besides looking back at history and around at the mounting populist momentum, Massachusetts Republicans might try to learn from a man who’s proven himself able to win elections in the state’s only possible swing district.

When Bill Keating was first elected to the Massachusetts Senate in 1984, it was on a platform of increased funding for police and education against a GOP opponent who hoped to ride Ronald Reagan’s coattails to the statehouse.

Massachusetts did vote for Reagan that year, like every other state but Minnesota. But 1984 was more about unique circumstances and movie-star looks than Reagan’s fateful combination of soft-hawkishness and soft-libertarianism—none of which could override decades of the state’s political heritage in the long run anyways. Keating understood that better than an opponent who overestimated the power of the Reagan moment.

That first Senate election offers good indications of Keating’s strengths: tough on crime, liberal on public benefits. Besides the campaign point of increased police funding, most of Keating’s key achievements in the state legislature were bills cracking down on drug-related and violent crimes. Despite his antipathy toward the Bulger camp and his ambitions to unseat them, Keating actually drew quite a bit from the old-school urban populism they represented.

Yet he did this while harnessing aspects of the Reaganite energy of the new age, including spearheading the effort to eliminate Massachusetts’ death tax in 1992. Though he was then and remains now a radical on social issues, Bill Keating quickly found a winning balance on economics that earned him an enduring reputation as a moderate.

Congressman Keating, maybe by accident, early tapped into an obvious truth that many new-wave populists seem to miss: people don’t like taxes. A conservative who wants to oust him will only win Bristol County by making sincere promises on public investment and public resources, but he’ll only win Plymouth County with a pledge to cut taxes and pare away bloat wherever it can be done, and he’ll only win Barnstable by harmonizing both. A new right in Massachusetts will have to be very careful not to overcorrect from the Reaganite errors of its predecessors.

Another lesson conservative hopefuls could take from Keating must have been learned the hard way in the “Beat Bulger” debacle. Keating the novice politician had little respect for the hyperlocal nature of proper politics. In more than a decade in the U.S. House, Keating the seasoned legislator has earned a reputation for diligence and expertise in important local issues, from struggling maritime industries to the now-closed nuclear power plant in my own hometown of Plymouth. 

Massachusetts Republicans, who are always tempted toward an abstract national paradigm detached from the concerns of their constituents, should take note: put immigration on the back burner and brush up on commercial fishing regulations.

In fact, kick the localism into overdrive. Aim for the kind of personal connection that made Keating’s white whale untouchable thirty years ago. True, there are almost 790,000 voters in the 9th district, many more than South Boston in 1993. But there are 730 days in each election cycle, give or take. Nominate a lifelong local with a superhuman capacity for pressing flesh and remembering names, and see how far he gets.

Run him on a campaign of economic populism, safe streets, strong schools, social conservatism, and lower taxes. Have him stump all across the district with speeches heavy on history; don’t let him pull any punches on rhetoric. See how an actual conservative challenge to nouveau liberalism fares in Massachusetts.

One full generation has passed since that liberalism came out swinging against the Massachusetts old guard. In the course of that generation, its victory has seemed conclusive. The last real conservative power-players in both parties went out in a mix of bangs and whimpers. Massachusetts, even South Boston and even the 9th district, has been written off by most as irretrievably lost to a left that arrived there yesterday.

But the arc of history is long, and “Beat Keating” has a bit of a ring to it.