Sympathy for The Donald

Those times of year I catch the Metro-North up to gather with the Westchester branch of my extended family, I have an ironclad rule: don’t talk about politics! They’re all ardent progressives, as I once was, and years ago as our views diverged there were a number of unfortunate instances when spirited disagreement flared into raised-voice disagreeableness I’d always regret afterwards. I love my family—they’re good well-intentioned educated people who’ve made up their minds, and I’m a good well-intentioned educated person who’s reached some different conclusions. Why argue?

That rule has generally worked out well, but was strenuously tested at Passover this year when within moments folks began dropping F-bombs (“Fascism!”) as the evening’s primary topic of conversation. The elephant in the room: that everyone knew I’d boarded the Trump train early on, and supported his candidacy three times straight, but we were all polite enough not to mention it. And so I nodded and stroked my chin and did my best to gracefully change the subject.

During the Seder itself, after the recitation of the plagues, a relative pulled out a sheet of paper and declared that there were also a bunch more plagues more apropos to 2025: deportations, tariffs, cuts to scientific research, and so on, with the capper “And rather than next year in Jerusalem, how about next year in American democracy?” All I could do was gaze out the window and try to keep my face expressionless until we could get back to the Haggadah.

The issue over which almost all of our arguments had taken place, and that most decisively alienated me from the Democratic Party, and that repeatedly proved such low-hanging fruit for Donald Trump, is immigration. Lest anyone leap to the conclusion that I’m some kind of xenophobe, some throat clearing. My mother is an immigrant, born to Holocaust survivors the year after the war, who was lucky to be adopted into an American family whose parents had come through Ellis Island a few decades earlier. I’ve had close friends from first-generation immigrant families since middle school. Most of my romantic involvements have been with women of color from immigrant families. The record couldn’t be clearer that I haven’t the slightest shred of xenophobia.

What I do have in abundance, though, is love for my Dad’s side of my extended family, largely working-class folk in Missouri I see at Christmas whose livelihoods have grown ever more precarious over the past few decades. Many of them make their livings in manual labor like tree-trimming, landscaping, contracting, and roofing, and the mass influx of impoverished migrants in recent years has not only undercut their wages but raised the costs of housing and strained the institutional resources and infrastructure that they rely on. Outsourcing had already taken most of the good jobs away, and in recent years it’s felt like importing cheap labor from elsewhere has claimed the lion’s share of what was left. From the perspective of someone equally invested in the dignity and material circumstances of my family in “flyover country” as my family in the Acela Corridor, Biden-Harris era migration policy proved not just distressing but alarming.

My stance on “illegal” or “undocumented” or “unauthorized” or “irregular” immigration, whatever one prefers to call it, is the traditional stance of organized labor and was the standard rhetorical position of the Democratic Party as recently as the 1990s, when I was growing up very liberal. There’s tons of footage on YouTube of figures like Bill Clinton, Joe Biden, Chuck Schumer, and the great Barbara Jordan forcefully articulating what remains my exact position today: that the United States’ immigration policies ultimately need to prioritize ordinary American citizens’ interests even as it’s also good to try to be generous. I harbor no personal animus against that vast majority of migrants who aren’t criminals and would likely attempt the same dangerous journey were I in their shoes.

Back in 1986, when Ronald Reagan signed the bipartisan Immigration Reform and Control Act, it was billed as finally solving the problem of illegal immigration once and for all. In exchange for legalizing roughly three million largely sympathetic migrants who’d already been in the U.S. for years, we’d finally get serious about protecting the U.S. labor pool by cracking down on employers who knowingly hired undocumented workers. But after a couple of years enforcement gradually petered out, which was a bipartisan failing: Democrats often liked to look the other way for humanitarian reasons, while the ascendent class of Chamber of Commerce Republicans were eager for as much cheap labor as they could get.

Then, in George W. Bush’s second term, there came a full-court press for another stab at “Comprehensive Immigration Reform,” this time legalizing around 12 million largely sympathetic illegal immigrants in exchange for enhanced border security that would supposedly finally solve the problem once and for all. Working-class Americans had heard that script before, and there was no reason to believe any serious attempt at sealing the porous border would actually be made beyond the first year or two. No, there could be no “Comprehensive Immigration Reform” until Washington demonstrated that it could be trusted to legitimately enforce the laws already on the books. I called both of my Missouri senators’ D.C. offices every day that the bill was under consideration nagging them to vote against it, and some of their staffers could get pretty nasty. It was a great relief when the legislation went down in defeat.

A few years later I was back on the phone urging my home state senators to oppose the DREAM Act that would grant citizenship to unauthorized immigrants who’d been brought to the United States as children. I’d had a close friend who was a “Dreamer” and didn’t want her or any Dreamer with a clean criminal record to be deported, but on principle opposed legalizing anyone illegally present in the United States until border security and interior enforcement alike were being handled in good faith. It wasn’t about wanting the Dreamers removed, but preventing a lather-rinse-repeat cycle of serial amnesties every decade or two that would incentivize ever further mass immigration to further undercut American labor.

Contrary to his “Deporter in Chief” moniker, Barack Obama actually presided over a comprehensive softening of the immigration system from top to bottom. What he couldn’t achieve via legislation he would surreptitiously engineer “by pen and phone.” As someone who spent years in progressive PR, I have my suspicions that the “Deporter in Chief” meme was astro-turfed into the news cycle to help Obama look tough and give him cover for eviscerating enforcement in the national interior. For one thing, the administration conflated removals from U.S. soil with migrants turned away at the border, enabling them to generate impressive and technically not untrue stats with far fewer of what the lay public would consider actual deportations. Then, claiming “prosecutorial discretion,” the administration declared that they were focusing on the baddest of the bad guys that much more strategically, but the policy amounted to an announcement to everyone on earth considering sneaking into the United States that they could more than likely stay forever so long as they stayed out of major felonious trouble.

In 2012, on a landmark day I still viscerally recall, President Obama announced he was unilaterally imposing Deferred Action for Childhood Arrivals (DACA), effectively legalizing hundreds of thousands of unauthorized immigrants by executive fiat despite his having previously acknowledged repeatedly that it would be unlawful for him to do so. My jaw dropped and my stomach lurched when I saw the news, so flagrant a violation it was of longstanding norms; my feeling that day was exactly what progressives have felt amidst Trump’s second term. Two years later came Deferred Action for Parents of Americans (DAPA, which was eventually blocked by the Supreme Court) arbitrarily exempting nearly all illegal immigrants with children from deportation. Absent any legislative authorization whatsoever, Obama managed to shift deportations from being a constant Sword of Damocles discouraging migrants from coming to a measure of last resort largely reserved for hardened criminals, thus encouraging ever more migrants to make their way to the United States.

Given Obama’s record on immigration, there was no way I could vote for a Democrat in 2016—especially after Bernie Sanders abandoned his principled career-long opposition to open borders as “a Koch brothers proposal” and became indistinguishable from the rest of the field. The Republicans weren’t much better, having bought into the official GOP 2012 campaign autopsy that the only way to compete amongst the changing electorate was to drop opposition to mass migration. I couldn’t possibly support Jeb Bush, who had famously described illegal immigration as an “act of love.” It’s not that I disagree with that characterization in probably most cases, but that my opposition to mass migration is just as much an “act of love” aimed at protecting my working-class loved ones. Supporting Marco Rubio was out of the question, as he’d repeatedly sponsored unacceptable “Comprehensive Immigration Reform” legislation, and Ted Cruz had proven himself wobbly, too. I’d never watched The Apprentice and had no particular affinity for Donald Trump, but he was the only major candidate who emphasized getting serious about immigration enforcement. I felt I had no choice but to support him, and was glad when he won.

People forget how ideologically flexible Trump was when he first got to Washington. It seemed to me that he primarily wanted to be popular, slap his name on a bunch of shiny new construction, and politically more or less split the difference between Arnold Schwarzenegger and Jesse Ventura. Had Democrats been willing to negotiate with Trump in something like good faith, he might have been the Nixon in China with the populist credibility to get some form of “Comprehensive Immigration Reform” over the finish line, albeit with a gleaming new border wall and much more enforcement than the Obama administration had singlehandedly made the new normal. Such a compromise wouldn’t have been the whole loaf that woke activists demanded, but it would have been more than half the loaf. But instead of negotiating, or even entertaining the possibility that Obama’s administrative maneuverings might have strayed too far for true public legitimacy, Democratic bigwigs by and large decided to double down on lawfare and #Resistance theatrics. Compromise was off the table, not just in terms of policy but even of rhetoric.

Most immigrants of my acquaintance are grateful and appreciative to be living in America. But I couldn’t help but notice in my years writing for Columbia Law School that the lawyers and activists who claim to speak for immigrants often have the opposite attitude: an overweening sense of entitlement and a penchant for “We Will Bury You”-esque discourse denigrating Americans of European heritage and mocking them for their shrinking share of the electorate. NYU journalism professor Suketu Mehta’s 2019 book This Land is Our Land: An Immigrant’s Manifesto, which argued that infinite immigration was but the arc of history bending toward justice and that Americans need to assimilate to newcomers rather than the other way around, neatly encapsulated what had become the conventional wisdom up at Columbia. I and probably most Americans find that sentiment offensive, but it had become par for the course among upscale progressives and Mehta’s book received glowing coverage on NPR (which may help explain why NPR’s federal funding got zeroed out this year).

I held my breath and hoped for the best when Joe Biden narrowly squeaked into office; I expected he’d probably restore the Obama administration’s counterproductive migration policies, but he had a generational opportunity to be a true statesman and historically great president by governing as he’d campaigned, as a center-left moderate lowering the temperature, restoring normalcy, and rallying Covid-battered Americans around an agenda the majority of citizens could get behind. For whatever reason, though, the Biden-Harris administration instead chose to proceed with shock and awe in precisely the opposite direction, particularly with regard to migration.

At the very height of the pandemic, as lockdowns were being vigorously enforced, the new regime moved literally on day one to extensively facilitate not just the unvetted entry of millions upon millions of impoverished migrants, but their rapid diffusion across the country at taxpayer expense as if to make it as difficult as possible to potentially remove them later. The scheme involved a cunning strategy that pro-migration NGOs had innovated under Obama and fully embraced during Trump’s first term, faced for the first time in decades with an administration making a real effort at reducing illegal immigration, to help migrants skirt the law and finagle long-term residency in the United States: NGOs started coaching prospective migrants on the precise script hitting all the talking points needed to apply for asylum and get admitted into the U.S. with quasi-legal provisional status, the intent being that the backlog for adjudicating those claims would grow so long that, even though the asylum would most likely be denied eight or nine years down the line, the migrants could then just disappear into the shadows until the next amnesty gave them citizenship. To close that loophole and disincentivize people from putting their lives at risk in making the attempt, the Trump administration had instituted the “Migrant Protection Protocols” requiring asylum seekers to wait outside the United States as their cases were processed. By ostentatiously dropping the Migrant Protection Protocols, the Biden-Harris administration essentially rolled out the red carpet for just about anybody who wanted to come and signaled to the entire planet that if they could get to a U.S. port of entry and recite a few magic words, they would very likely score very likely permanent residency.

Inevitably, a sea of migrants flooded to the southern border for their promised golden tickets. I don’t blame them for that—they were responding rationally to the Biden-Harris administration’s reckless action. As if throwing open the borders wasn’t irresponsible enough, the Biden-Harris administration also immediately halted construction of the border wall (later auctioning off the surplus materials for a fraction of what they’d cost) and announced that they were essentially exempting almost anyone but hardcore felons who’d been physically present in the United States before November 2020 from any threat of deportation. The very day that Joe Biden was inaugurated, he largely dismantled immigration enforcement by stroke of autopen, and then throughout his term indiscriminately handed out temporary protected status to over a million more impoverished migrants.

I don’t buy some of the more hyperbolic claims about the number of migrants the Biden-Harris administration ushered in or otherwise became “gotaways.” Some MAGA conservatives claim the number is 20 or 30 million, which doesn’t add up from the stats I’ve seen, but something in the vicinity of 10 million in just three and a half years is a reasonable estimate. Throughout the crisis, with thousands of migrants streaming into the U.S. every single day, the administration swore up and down that they were doing everything they could to secure the border and that Congress needed to pass new legislation for “Comprehensive Immigration Reform” giving them the tools they needed. But since they weren’t using the tools they already had, there was no reason to believe they would legitimately enact any of the token border security provisions tacked on to the massive amnesty they were so eager to pass. As the administration demonstrated when it eventually tightened up the border in Spring 2024, in what seemed a belated effort to neutralize migration as a campaign issue, it could have done so at any time: the border crisis wasn’t driven by climate change, as officials frequently liked to claim, but in fact by a deliberate series of coordinated policy decisions intentionally implemented by the Biden-Harris administration and allied NGOs, however valiantly Matthew Yglesias argues otherwise.

So why did they do it? Why did they persist with such deeply unpopular policy over such vast public outcry that ultimately drove even Hispanic voters into the waiting arms of Donald Trump? I will give the administration the credit that in their minds and epistemic bubble they probably saw themselves as enlightened humanitarians uplifting the Global South’s downtrodden. They probably looked at the statistics of an aging America with low fertility rates and figured migrants could fill jobs in occupations where there really are some legitimate labor shortages. In terms of realpolitik, they likely presumed that more eventual voters of migrant backgrounds would be a boon for the long-term prospects of the Democratic Party, and hoped that the unprecedented spectacle of so many migrants entering day by day might demoralize border hawks into throwing up their hands and concluding that resistance was futile. But the single biggest motivation, I believe, was spite. Immigration had been The Donald’s signature issue, so the new sheriff in town was going to rub Trump’s deplorable xenophobic supporters’ faces in more migration than they’d even imagined possible. The Biden-Harris administration wanted to ritually humiliate Trump voters, to put them in their place once and for all, and that was more important to them than public opinion or their constituents’ material interests.

It was offensive and wrong for Donald Trump and J.D. Vance to suggest that the Haitian migrants placed in Springfield, Ohio were eating people’s pets. I condemn that. But in the grand scheme of things, it was more offensive and wrong for the Biden-Harris administration to suddenly settle 20,000 impoverished migrants in an already struggling small city of 40,000 residents. To the extent that large numbers of desperately poor migrants get dumped into communities, it should be in locales affluent enough to uplift the newcomers: places like Martha’s Vineyard, Scarsdale, Chevy Chase, Aspen, and Malibu. Each of those tony enclaves voted lopsidedly for Joe Biden and Kamala Harris, and have lots of outspoken citizens proclaiming their solidarity with migrants, so it’s puzzling that they haven’t stepped up to do their part.

Had Kamala Harris managed to get elected president after the unprecedented migration free-for-all, I suspect the administration would have turned the spigot back the day after the election to welcome in at least 10 million more migrants by 2029. Indeed, I fully expect that any Democratic president who can make it through the primaries for the foreseeable future will reopen the floodgates on their Inauguration Day. So in assessing Trump-Vance immigration policies, I’m considering not just what’s happening now and through January 2029, but gaming out how to preemptively limit the damage of a prospective Buttigieg or Ocasio-Cortez presidency.

However harsh it might sound to some ears, the key to deterring mass migration is for people considering migrating to the United States to know that they’d really be taking their chances; there has to be a high degree of probability that they’ll get turned away at the border time and time again, and then if they finally manage to sneak in that there will be a solid chance that they’ll eventually be deported, even if it’s for something as minor as a DUI ten years later. There simply must be a credible and ongoing risk of deportation, or else endless waves of impoverished migrants have no reason not to come. The Biden-Harris policy enticed millions and millions considering migrating into believing that they were perfectly welcome to enter the country and would have virtually no chance of being deported unless they were gang members or terrorists, and even that was negotiable: sanctuary city prosecutors routinely downgrade migrant gang members’ felonies to misdemeanors to help them remain in the country.

I don’t disagree with my progressive friends and family that the Trump-Vance approach of dispatching federal officers to chase down and tackle day laborers in Home Depot parking lots is cruel political theater not particularly effective at nabbing very many migrants and that frequently results in civil rights violations of American citizens, but it’s not without its brute logic. Most people have smartphones nowadays, even in poor countries, and the upsetting viral footage of random migrants’ hopes being dashed and their new lives being ruined is potent evidence that making the arduous journey to the United States just isn’t worth it, and still won’t be worth it even when the next Democratic president casts open the borders again. So far, in its brass-knuckled way, the approach has kind of been working: practically no migrants are entering the country and something like two million people have already either been removed or left voluntarily. It’s an awfully mean strategy, and by no means what I’d have chosen, but the greater cruelty was the Biden-Harris administration encouraging millions of people who had so very little to upend their lives and sacrifice everything to rush up to the United States when an ugly backlash was so predictable and inevitable. Anything short of a strong majority of the ten million migrants who flooded in between 2021 and 2024 being removed or departing of their own accord would be a vindication of the Biden-Harris policy, and all the more encouragement for the next Democratic president to do it all over again.

The performative cruelty plays another purpose as well: it’s chum for the angrier and perhaps more prejudiced segments of the MAGA base with utterly unreasonable expectations of removing every last illegal immigrant from the United States. If the Trump-Vance administration were truly gung-ho about mass expulsions, there’s a much easier way than what ICE has been doing. They could start raiding poultry plants in Arkansas and almost effortlessly round up tens of thousands of migrants in single fell swoops. But that would send the price of chicken skyrocketing, and nobody wants that. Instead, the administration is delivering vibes-based wildcat immigration enforcement nudging recent arrivals in particular into concluding that self-deportation is in their self-interest while mostly overlooking longer-standing populations of illegal immigrants who have become structurally important to the economy and who have the strongest claim of deserving legalization.

I personally regard Biden-Harris migration policy as the starkest abuse of executive authority since Japanese internment, dwarfing any and all of Donald Trump’s abuses in office thus far. But that doesn’t mean there aren’t far too many good people who’ve done nothing wrong getting caught in the crossfire. My own dear mother applied for her REAL ID earlier this year so that she could board a plane, and we had to dig out her tattered old naturalization documents from the 1940s for the feds to review. She did get her REAL ID eventually, but it took a lot longer than it should have, and I couldn’t escape the impression that the long delay was intended to convey a message. There are some siblings I happen to know whose parents have legally resided in the U.S. for decades bouncing between the banking sector and working as diplomatic functionaries for their home country’s government. As far as each sibling knew, they were all U.S. citizens, but it turns out under scrutiny that even though they were all born at the same hospital during the same number of years, two of them are legally not citizens due to the fine print of their parents’ specific employers on their particular dates of birth. Year after year they voted and did jury duty when summoned and all the other things good citizens are supposed to do, because both they and the government had no idea that they weren’t technically eligible to do so. One of them married an American citizen and started an American family; one of them even voted for Trump. And now their statuses are up in the air and they’re being treated like criminals—they can’t apply for business loans or travel internationally, and live in constant terror that jack-booted thugs will kick down the door and drag them away. It is little exaggeration to say that the Trump-Vance administration has arbitrarily ruined their lives. Cases like theirs are an outrage that cannot stand.

Joe Biden threw away his opportunity to transcend the political moment and become a true statesman who might be remembered fondly. Today, Donald Trump is veering down a similar path. True, Biden broke his promise to try to restore normalcy, while Trump is governing as the wrecking ball he promised in his campaign, but the sloppiness and brutality of present migration policy is increasingly discrediting the very concept of immigration enforcement among many moderates who might otherwise have been inclined to seek compromise.

The truth is, America is in desperate need of compromise. Millions of border hawks like me have to acknowledge that most illegal immigrants aren’t bad people and that millions of them hold undesirable bottom-rung jobs that not enough Americans are willing to do. Those workers and most of the Dreamers, at very least, deserve to be legalized. But by the same token, pro-migrant advocates need to acknowledge that the benefits of mass migration have primarily accrued to the migrants, and to the affluent people who enjoy cheaper labor, while the costs have disproportionately been borne by working-class and middle-class American families that were already hurting and have seen their livelihoods dramatically eroded in recent years. H-1B abuse is real and has been endemic for years. The country needs a robust deportation protocol and hermetically sealed borders to fight the cartels and protect the American labor pool. A genuine compromise on systemic immigration reform would be a great achievement, but the legislation Washington has offered up for decades has so patently been a bait and switch aiming for all of the amnesty and none of the enforcement.

So long as the Senate filibuster endures, migration issues have grown so polarized that it’s hard to imagine Congress being capable of passing any major migration legislation for the foreseeable future. If Democrats retake the majority, abolish the filibuster, and pass a massive amnesty with 51 votes, though, they’ll soon regret it; the next Republican majority would find a way to rescind that amnesty with a draconian ferocity making Donald Trump and Stephen Miller look like kindergarten teachers. It’s in everyone’s interest to pursue real political legitimacy and avoid widening the gyre any further.

So, were I advising President Trump, this is what I’d suggest. Migrants are rational actors, and ten million arrived in under four years because Biden-Harris policy made it crazy for them not to come. The priority should be to readjust the incentive structure such that the rational decision is for migrants to leave voluntarily. Unpredictable worksite raids are an essential tool to instill a credible fear of deportation, but there are also gentler ways to encourage people to repatriate. The administration has already instituted a program offering migrants $1000 and a free plane ticket back home. I would suggest experimenting with doubling that cash amount to $2000 or more with a guarantee that if they wish to apply for legal residency through proper channels their history will not be held against them. At the same time, I’d seek possibilities of withholding a meaningful fraction of the federal dollars annually dispensed to sanctuary jurisdictions to help incentivize them to respect federal law. And, I’d administratively exempt from deportation any illegal immigrant with a spotless criminal record who can prove they were present in the United States before January 2009, when Barack Obama began administratively demolishing the immigration system that Congress had established. Those migrants have put down roots, likely have children who are American citizens, and have become significant to our national economy—there’s little compelling reason to remove them at this point.

At the end of the day, we the American citizenry can’t even begin to consider what we might owe outsiders knocking on our door without first figuring out what we owe each other as fellow Americans, in our dysfunctional national family. One thing we no doubt owe one another is a more honest conversation on how relatively open versus relatively closed borders variously impact different echelons of our society. Carefully managed immigration can be a win-win for everybody, I believe, but rash Obama-Biden-Harris migration policies directly made many millions of vulnerable Americans’ lives worse. My progressive friends and family would do well to extend some more of their commendable compassion for migrants to their struggling fellow Americans, no matter who they might have voted for.

Was pleased to appear on Daniel Oppenheimer’s Eminent Americans podcast discussing the uncertain future of NPR, along with Mark Oppenheimer and Mike Pesca…

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