In 1999, Rahm Emanuel had just left the Clinton White House, taking a short break from public service to do a stint with a Chicago-based investment bank, Wasserstein Perella & Co. By the time he was elected to Congress in 2002, he had banked more than $16 million. “Frequently, Emanuel turned big Democratic donors and others he’d met during his White House years into clients for Wasserstein Perella, a firm that was led by Bruce Wasserstein, a hefty financial supporter of Clinton,” Politico would later report, noting that Emanuel developed “a reputation as a deal guy who focused on mergers and acquisitions among companies that were subject to heavy government regulation.” That same year, New York Times columnist Maureen Dowd won a Pulitzer Prize for her columns on the Monica Lewinsky scandal, which consisted of the famously tart stylist slaying the former White House intern for her diet, her feelings for President Bill Clinton, her shopping, and her alleged money-grubbing. After Republicans lost seats in the ’98 midterm elections, Dowd penned a column, declaring the saga over, and lamenting the tragedy that Lewinsky would now be unable to cash in.

From left, then-House Minority Leader Nancy Pelosi gathers with then-Democratic Congressional Campaign Committee Chair Rahm Emanuel, then-Democratic Senate Campaign Committee Chair Chuck Schumer, and then-Senate Minority Leader Harry Reid at a midterm election night party for the Democratic Party on Nov. 8, 2006, in Washington, D.C. Photo: Brooks Kraft LLC/Corbis via Getty Images

“Ms. Lewinsky was one of the big losers in the election. She lost her chance to be Oliver North and rivet the country at a Congressional hearing. So now all she has to sell is her voice. It is all that hasn’t been heard. It is a voice that men say they find alluring, not the ditsy Valley Girl voice the world is expecting,” Dowd opined. “Poor girl. No wonder she’s in a bad humor. Her commercial window of opportunity is slamming shut.” Of course, the fight wasn’t over, and Republicans would in fact pursue impeachment despite the election results, but it was good enough for Pulitzer work. “Monica must be in a panic to squeeze the last drop of profit from this sordid tale,” the columnist observed. (Or, perhaps it wasn’t good enough. She neglected to include that column in her Pulitzer submission.) We know little about how the deals Emanuel so lucratively cobbled together during that time worked out for the companies — or their workers — in the end, but we do know how things have gone for him and Dowd ever since. Just wonderfully, thank you.

Emanuel would go on to become chair of the Democratic Congressional Campaign Committee in the critical wave year of 2006, then White House chief of staff, then mayor of Chicago, and now back to banking, along with sinecures at The Atlantic and ABC News. Dowd has continued to have and share opinions, and the pair came together last week to referee the debate between “the Squad” — the four freshmen women who’ve shaken up the House of Representative — and Speaker Nancy Pelosi over the appropriate response to the crisis at the border. The purpose of her newest column is to simultaneously humblebrag — “Writing a column that sparks an internecine fight among the highest-profile women in the Democratic Party is nerve wracking” — and disclaim responsibility for starting that fight — and put it on me instead. The A.O.C. crew threw down the gauntlet in a recent opinion piece in The Washington Post by The Intercept’s Ryan Grim. He wrote that when Pelosi and other Democratic mandarins try to keep the image of the party centrist, they are crouching in “the defensive posture” they’ve been in since the Reagan revolution. Corbin Trent, a spokesman for A.O.C. and co-founder of Justice Democrats, the progressive group that helped propel her, told Grim: “The greatest threat to mankind is the cowardice of the Democratic Party,” with the older generation “driven by fear” and “unable to lead.” Message: Pelosi is past her prime. Both Dowd and Emanuel rose through their acerbic wit and slashing rhetoric, and they have often been a joy to behold; even if they weren’t making sense, they were fun to watch. As the years have worn on, though, they’ve lost some juice on their fastballs. Twenty years ago, Dowd would never have needed to dial a friend for help demolishing the target of a column — in this case, Rep. Alexandria Ocasio-Cortez and her chief of staff, Saikat Chakrabarti — but could dispatch of the task solo, like a proper assassin. Yet had she gone to Emanuel, known for his creative use of foul language, back then, he’d have dished her out a memorable put-down, the kind that can stick with a person for the rest of their career. Instead, Emanuel wound up, reared back, and fired off his best heater: Chakrabarti, Rahmbo declared, is — wait for it — “a snot-nosed punk.” “What votes did you get?” sniffed Emanuel. “We fought for years to create the majorities to get a Democratic president elected and re-elected, and they’re going to dither it away.” What was most startling, and most instructive about the rot at the heart of today’s politics, is that Dowd’s column didn’t touch on the actual issue that the Squad and Pelosi were litigating — namely President Donald Trump’s cruel and inhumane treatment of asylum-seekers and other immigrants at the border. Even more startling was that Emanuel was allowed anywhere near that question. When it comes to immigration, both the politics and the policy, perhaps no Democrat has been more destructive over the past 25 years than Rahm Emanuel. For people who have come to understand politics in a post-Great Recession era, the immigration debate during the mid- to late 2000s would be entirely unrecognizable. In 2005, President George W. Bush teamed up with Sens. John McCain and Ted Kennedy on a push for comprehensive reform, and there was genuine optimism that it could happen, giving a path to citizenship for people here without proper documents, as had happened under Ronald Reagan just two decades earlier. In some ways, having Bush in the White House was better for reform’s prospects than under Clinton. In the 1990s, Democrats had been the party of immigration enforcement, with Emanuel urging Clinton to get as tough as possible. Bush, waging war around the globe and clearing brush on his ranch with a cowboy hat, was confident in his reputation for toughness, so he didn’t mind compromising on the issue. As a border-state governor, he also had a better understanding of the realities of the immigration system. As a pro-business Republican, his fealty to the Chamber of Commerce pushed him further toward reform.

In some ways, having Bush in the White House was better for reform’s prospects than under Clinton.

While the Senate worked on its 2005 proposal, Republican hard-liners were whipping up their own hysterical bill in the House, led by Wisconsin Rep. Jim Sensenbrenner. Co-sponsored by Peter King, R-N.Y., it was a preview of the rightward lurch of immigration politics to come. It included no pathway to citizenship, no protections for people already in the country, not even a guest worker program. It criminalized immigration violations that had long been civil affairs, turning even a visa overstay into an “aggravated felony,” empowering local and state police to become immigration enforcement officers. The bill also made it a felony to aid someone in the country illegally in any way, and funded new fencing on the border and a surveillance and monitoring regime in the interior of the country. As the vote approached, the Congressional Hispanic Caucus met to talk strategy. One of its most conservative members, John Salazar, who represented a swing district in Colorado, gave a rousing speech, saying that this was a moment to stand together, according to a CHC member in the room. Salazar pledged to oppose the Sensenbrenner bill. “For the first time, Latinos were going to vote as a caucus, not talk smack but actually go out and vote,” said the CHC member, who asked not to be named so as to stay out of Emanuel’s crosshairs. But the unity wouldn’t last. “Rahm went to Salazar and told him, ‘Don’t expect any money from the DCCC, or my help, if you vote against Sensenbrenner,’” the CHC member said. It was a painful choice to make. “Salazar’s wife was like, ‘This is a piece of shit legislation.’ I remember her saying that.”

Photo: Win McNamee/Getty Images

Emanuel, serving by then as chair of the DCCC, saw an opportunity for a win-win. Bush wasn’t going to sign the bill, and the Senate would never pass it, he argued, so it was essentially a free vote. He urged moderate and conservative Democrats to back the bill, including Chicago freshman Melissa Bean, whom he had helped elect in 2004. That would burnish their conservative credentials, but there would also be an added benefit for the party: The bill was so vicious and racist that it would prompt an outpouring of anger from the Latino community, which Emanuel hoped to channel into votes in the 2006 midterms. “I remember immediately after that, he was like, ‘We’re gonna take the majority over.’ Rahm was gonna do what Rahm was gonna do. If that meant telling Latino members of Congress to vote against their conscience, that’s what he was gonna do,” said the CHC member.

“Rahm was gonna do what Rahm was gonna do. If that meant telling Latino members of Congress to vote against their conscience, that’s what he was gonna do.”

Emanuel was right that the immigrant rights community would respond forcefully. The bill passed in December 2005 with just 203 Republican votes, 15 short of the 218 needed. But 36 Democrats put it over the top, including Bean and Salazar. The name Sensenbrenner became profanity on Spanish-language TV and radio, and the Latino community mobilized millions in mass demonstrations. The protests began in Chicago, with 100,000 taking to the streets in March 2006. Then more than a million people rallied in Los Angeles. In April, simultaneous protests erupted in 102 different cities. On May 1 — May Day, honoring workers and unions — millions across the country again took to the streets. As the protests grew, so did the backlash. Right-wing radio was obsessed with Mexican and Central American flags being flown at the rallies, and counterprotesters began burning Mexican flags at their own demonstrations. Membership in the Minutemen, an anti-immigrant militia, surged. States and cities passed their own draconian laws, such as Arizona’s notorious SB 1070. U.S. Immigration and Customs Enforcement responded by stepping up raids. Emanuel may have thought working to pass the legislation would be harmless, but deportations soared in the final two years of the Bush administration, with ICE feeling emboldened to hit back at organizers of and participants in the demonstrations. ICE has been on a war footing since. The move helped unleash a wave of nativism that has only grown more powerful as the years have gone by, culminating in the election of Trump in 2016. “Rahm epitomizes the spineless approach to immigration that many in the Democratic Party have taken for three decades,”said Angel Padilla, national policy director of the Indivisible Project. “Under Clinton he helped criminalize immigrants, and under Obama he got in the way of permanent relief for families.” Emanuel did indeed get this slight uptick in the Latino vote share: Hispanics were more likely to vote in the 2006 midterms because of the Sensenbrenner bill, according to a study in “The Almanac of Latino Politics” called “Immigration and Its Impact on Latino Politics.” Photo: Gina Ferazzi/Los Angeles Times via Getty Images

Two years later , when Barack Obama was elected president, he brought Emanuel on as his chief of staff. Early in Obama’s term, it became clear that his campaign promise to move quickly on immigration reform wasn’t going to be kept, particularly as the tea party protests rocked the summer recess of 2009. “There’s always a sense that no matter how hard we work, to get through the White House, we have to get through Rahm,” said Rep. Raul Grijalva, D-Ariz., in 2010, quoted in a Los Angeles Times article headlined, “Democrats point the finger at Obama’s chief of staff for immigration reform’s poor progress.” “I would like immigration not to be part of the chief of staff’s portfolio. It would make our ability to convince and access decision-makers in the White House a lot easier,” Grijalva said. “It’s going to be much easier for this issue to move after Rahm Emanuel leaves the White House,” Simon Rosenberg, head of the New Democratic Network, added in the same article. “Rahm has a long history of a lack of sympathy for the importance of the immigration issue.” Dreamers, the name given to undocumented people whose parents had brought them to the United States when they were children, began to put pressure on the White House and on the immigrant rights community itself. They formed the group United We Dream in 2009, pulling together disparate youth organizations that had been shut out of the larger infrastructure. In May 2010, a more radical group, The Dream Is Coming, took what was the first step on the path the movement has been on since. Five undocumented people sat down in McCain’s Senate office, demanding that the Arizona Republican support the DREAM Act as he had before. Four were arrested, with three given deportation orders. In July, New York Dreamers pressured Sen. Chuck Schumer with a 10-day hunger strike. In November and December, a 43-day hunger strike in San Antonio sought to pressure Sen. Kay Bailey Hutchison, a Republican who had previously backed the DREAM Act but was now wobbly. In November, Democrats were washed out of the House by the tea party wave and lost six seats in the Senate (in addition to the one they had already lost to Scott Brown in January in the special election). The lame duck was the last chance. Activists flooded phone lines, staged sit-ins, and launched new hunger strikes. The bill passed the House, still controlled by Pelosi, and got a Senate vote on a Saturday morning in December. The immigration reform legislation carried the day by a vote of 55-41, but because Democrats hadn’t eliminated the filibuster, it needed 60 votes to pass. It fell five short, with six Democrats against it. “This bill is a law that at its fundamental core is a reward for illegal activity,” crowed Jeff Sessions, then a senator from Alabama.

A new immigration approach did not come naturally to White House officials.

On December 21, with the window for legislative action closed, Obama reached out to Luis Gutiérrez, then a Chicago congressperson. “He calls and he says to me, ‘We lost the House, and we’re weaker in the Senate. So now I have to defend immigrants, and we need to defend them together,’” Gutiérrez told me. “So he says to me, he says, ‘Luis’ — I remember exactly the words — ‘I want you to put your thinking hat on. I know you’re going to Puerto Rico. You know I’m going to Hawaii’ — it’s kind of jovial, right? — ‘and when we get back, give me your best ideas on how we protect them.’” From there, Gutiérrez said, came the executive orders and memos on prosecutorial discretion that would reverse the administration’s approach to immigration. But a new immigration approach did not come naturally to White House officials. “I come back [in February 2011] and I meet with [new chief of staff] Bill Daley,” Gutiérrez said. “Bill Daley’s response was, ‘Well, wouldn’t Mexicans just cross the border en masse to find American citizens to get married to?’ And I almost fell under the table. ‘Uh, yeah, some really poor Mexican migrant workers are gonna find willing American citizen women to just marry them. Uh, I think we have a little problem here.’”