THE DETENTION OF and planned deportation of Mahmoud Khalil, the Columbia University protest leader, has shocked even some of the Trump administration’s most jaded critics. But such aggressive tactics have a long history in the United States—look no further than the case of yet another strident left-wing activist, the labor leader Harry Bridges, who fought efforts to deport him to his native Australia for some twenty years, starting in the late 1930s. Bridges’s story is worth recounting at length, not only because it so closely parallels the present—and hints at where the administration may go next—but because it also suggests how a new wave of similar government overreach might be avoided.

Born in Melbourne and a seafarer from his early teens, Bridges had traveled the world before walking down a gangplank in San Francisco in 1920. He immersed himself in the radical labor politics of the city’s waterfront, and in 1934 led a general strike all along the West Coast, calling for better pay in the depths of the Great Depression. The strike had mixed results, but it established Bridges as a leading voice of West Coast labor.

But he wasn’t just an energetic and radical labor leader—he was also a cooperator with, and possibly a member of, the Communist Party. Like loyal party members, he backed American involvement in the fight against fascism in the 1930s, then reversed himself in 1939, when Hitler and Stalin signed a non-aggression pact, then flipped again after Germany invaded the Soviet Union in 1941. Years later, he opposed the Marshall Plan and NATO, and backed the third-party presidential campaign of Henry Wallace, a progressive who received significant help from the Communists. Bridges’s degree of affiliation with the Communist Party USA or with Moscow was repeatedly a point of legal contention, including in multiple Supreme Court cases, and the main impetus for the attempts to deport him. The exact nature of his relationship with the Communists remains unclear. In 2023, Emory University historian Harvey Klehr recounted having seen a document in the Russian archives in the 1990s seeming to list Bridges as a member of the Central Committee of the Communist Party USA. But even amid the true spy scandals and anti-Communist hysteria of the 1950s, the rule of law held and Bridges’s rights were protected.

Bridges’s outspoken radicalism made him a target for Franklin Roosevelt’s administration, whose attitude toward organized labor was often more complicated than history remembers. The White House liked union leaders as long as they cooperated with FDR’s agenda. Those who pushed against it, like Bridges, were branded as enemies and dealt with accordingly. Roosevelt could count for support on other, more conservative union leaders, as well as a growing rank of business alliances and patriotic groups convinced that Communist subversion was an imminent threat to America.

The Labor Department first tried to deport Bridges in 1938, based on charges that he was, or at least had been, “affiliated with” the Communist Party. The case was supported by a voluminous, and vacuous, FBI file. “Our report confirms the belief that Bridges is a Communist and that the Communist party advocates overthrow of the United States government,” FBI Director J. Edgar Hoover said, despite having nothing of the kind. The testimony of some of the star witnesses appeared coerced. The proceedings quickly fell apart.

In 1940, responsibility for enforcing immigration laws was transferred from the Labor Department to the Justice Department, which took up the Bridges case using a new statute, the Alien Registration Act, better known as the Smith Act. The law allowed the government to eject non-citizens accused of radical affiliations—in Bridges’s case, with the Communist Party. This time the government won initially but lost on appeal. Since this was a deportation proceeding, not a legal trial, it went to Attorney General Robert Jackson for review. He decided against Bridges.

But Bridges wasn’t done. He took his case to the Supreme Court. In a 1945 decision, a 5–3 majority found that the lower courts had interpreted the term “affiliation” too broadly in Bridges’s case. In the relevant statute, the Court held, “affiliation . . . must be more than merely in sympathy with its aims or even willing to aid it in a casual intermittent way.” It required “an element of dependability” that might stop short of actual membership, but had to be more than casual. As for Bridges’s membership, the Court ruled that the evidence the prosecution used was collected improperly and that “since Harry Bridges has been ordered deported on a misconstruction of the term ‘affiliation’ as used in the statute and by reason of an unfair hearing on the question of his membership in the Communist party, his detention under the warrant is unlawful.”

In explaining why they were requiring strict standards of evidence, the majority noted that “Though deportation is not technically a criminal proceeding, it . . . deprives [Bridges] of the right to stay and live and work in this land of freedom.” As if writing a warning for today, the justices continued, “Meticulous care must be exercised lest the procedure by which he is deprived of that liberty not meet the essential standards of fairness.”

Justice Frank Murphy, a pro-union former governor of Michigan, was unsatisfied with merely finding in Bridges’s favor. In a concurring opinion, he outlined a decade-long “concentrated and relentless crusade” by “industrial and farming organizations, veterans’ groups, city police departments, and private undercover agents” to have Bridges deported. And in words that echo today in Khalil’s case, Murphy added that “once an alien lawfully enters and resides in this country he becomes invested with the rights guaranteed by the Constitution to all people within our borders. Such rights include those protected by the First and Fifth Amendments and by the due process clause of the Fourteenth Amendment. None of these provisions acknowledges any distinctions between citizens and resident aliens.”

The government’s campaign catapulted Bridges into the pantheon of left-wing heroes. The Citizens Committee for Harry Bridges collected legal and financial resources, and gathered celebrities like Orson Welles and Lillian Hellman to lead marches and mass meetings. Pete Seeger and the Almanac Singers (with Woody Guthrie in the chorus) cut a record called “The Ballad of Harry Bridges.”

FIVE DAYS AFTER the 1945 decision, Bridges filed his paperwork to become an American citizen. The examiner asked if he had ever “belonged to any organization that advocated the overthrow of the government by force or violence,” or if he had ever “belonged to the Communist Party in the United States.” He answered, “No,” to both questions.

So began Bridges’s next legal peril. In 1949, the government accused Bridges of lying about his Communist Party membership. He was convicted by a jury, stripped of his citizenship, and ordered deported. While he appealed, the Congress of Industrial Organizations, an umbrella labor group, ejected his union, the International Longshore and Warehouse Union, on charges that it was linked to the Communist Party. After the Korean War broke out in June 1950, the government imprisoned him for three weeks, on the premise that his outspoken criticism of the war was a threat to national security; in protest, thousands of dock- and farm-workers walked off the job.

In 1953, Bridges’s case once more reached the Supreme Court, which once more found in his favor—though on a technicality, overturning Bridges’s conviction on the grounds that the statute of limitations had lapsed before he was indicted.

After losing at the Supreme Court for a second time, the government gave it one final shot, taking its case to civil court. But after losing yet again, the government finally dropped its campaign in 1955. Bridges returned to his labor work and remained the leader of the West Coast longshoremen until 1977. He died in 1990.

Late in life, Bridges conceded that “95 percent of the evidence against me is true.” But he maintained that “one thing I didn’t do, I didn’t happen to be affiliated with the Communist Party.”

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THE PARALLELS BETWEEN Bridges’s case and Khalil’s are obvious: Like Bridges, Khalil is a non-citizen who took up unpopular positions, which in turn made him a convenient target for an administration eager to rein in dissent. The initial proceedings against Bridges essentially amounted to accusations that he sympathized with a radical organization. The case against Khalil is, if anything, even weaker, because sympathizing with Hamas is not a crime.

But the similarities run deeper. Bridges was the first of scores of resident aliens prosecuted for their beliefs in the 1940s and ’50s, many of whom were deported. The government has yet to charge Khalil with a crime, but if it does, it could well rely on the Smith Act, elements of which Kristi Noem, the secretary of homeland security, has already reactivated. Whatever the statute, the underlying argument will be just as dangerous: Pace Justice Murphy and the 1945 Court, non-citizens are not to be afforded the same civil liberties as citizens.

On a more positive note, one reason Bridges won was the immense political and financial support that rallied behind him. So far, there seems to be similar energy behind Khalil, though at this point it remains focused on passionate protest rather than long-term organizing. For Khalil’s sake and for that of the many who will surely follow him, that needs to change soon.

For all the stress and strain that the years of accusations, prosecutions, and lawsuits must have caused Bridges personally, in the end, the system worked. In the face of an extended, aggressive government campaign against him, and at a time of heightened national security concerns when judicial deference to the government might have been expected, the Supreme Court consistently hewed to the rule of law, finding in favor of a man despised by presidents, powerful business and union interests, and millions of everyday Americans.

In fact, Khalil’s chances are better precisely because of what Bridges went through. Groups like the ACLU and the CIO mostly refused to support Bridges, and it was hard for him to find legal defense. But America’s civil liberties sector seemed to learn a lesson from the case, and the Red Scare in general, and since the 1950s has proven stalwart in the face of government intrusions on civil liberties, even against people with deeply unpopular beliefs.

President Trump has made clear that there will be more cases like that of Mahmoud Khalil. But what he might get is more cases like that of Harry Bridges—more confirmations of fundamental civil rights in the face of a twenty-first-century Red Scare.

Clay Risen is the author of Red Scare: Blacklists, McCarthyism and the Making of Modern America, just published by Scribner.