Durbin’s looming legacy
Plus: How Democrats escalated their oversight of Trump deportations and the intensifying economic backlash against the president ahead of his official 100-day mark.
👋🏾 Hi, hey, hello! Thank you to everyone who sent birthday wishes yesterday. Let’s catch up: Pope Francis, who redefined the modern papacy as a force for global diplomacy and social justice, died this week at 88. … President Donald Trump accused Ukrainian President Volodymyr Zelenskyy of sabotaging peace negotiations by refusing to recognize Crimea as Russian territory. … Jordan Wood, former chief of staff to then-Rep. Katie Porter (D-Calif.), launched a campaign to unseat Sen. Susan Collins (R-Maine)—a rare Democratic Senate pickup opportunity in 2026. … Rep. Haley Stevens (D-Mich.) entered the race for Michigan’s open Senate seat, and fellow Michigan Democrat Hillary Scholten quickly endorsed her bid. … Rep. Jim McGovern (D-Mass.) announced the heartbreaking death of his daughter, Molly, who passed away in Italy after battling a rare form of cancer. … The Congressional Progressive Caucus PAC endorsed Harris County Attorney Christian Menefee in the special election to replace the late Representative Sylvester Turner (D-Texas), who died suddenly last month. … The Democratic National Committee committed to investing $1 million per month in state parties over the next four years, increasing its share of national funding from eight percent to more than 20 percent. … Senate Democrats called on the acting Social Security watchdog to investigate how DOGE has disrupted service for millions of clients. … Two Senate Democrats sent a letter opposing the Trump administration’s plan to privatize the U.S. Postal Service. … 90 House Democrats urged Treasury Secretary Scott Bessent to reverse an executive order that cuts economic revitalization funding for distressed communities nationwide. Keep reading for what else is worth knowing from the Hill this week—straight from my notebook to your inbox.
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Durbin’s retirement marks the end of a Senate era
Sen. Dick Durbin’s retirement announcement is more than a political headline—it marks the end of a Senate era where workhorses thrived, influence was earned through policy chops, and power didn’t require a viral moment.
Allow me to explain: While the announcement set off the early stages of a major reshuffling in Illinois politics and within Senate Democratic leadership, it’s also a deeply personal moment for those who came up under Durbin. For many staffers, he embodied what leadership in public service was supposed to be.
In his own words: “You could always count on Dick Durbin to do the right thing and be on the right side of history on everything from education to criminal justice reform to pocketbook issues to help working families to everything in between,” Michael Hardaway, who interned for Durbin in 2005, told Once Upon a Hill.
Hardaway, who went on to work for former President Barack Obama and then-House Democratic Caucus Chair Hakeem Jeffries, told me he didn’t have much exposure to politics growing up.
But while in Durbin’s office, he shadowed the senator at community events, speeches, and virtually everywhere else in between.
“The fact that this really important guy had confidence in me to bring me along, let me meet people that he knew and be part of the group that represented him when he would go places was important to me.”
In the know: Durbin’s decision to retire also marks the end of a career rooted in a political era that rewarded policy mastery and persuasion over performance.
For decades, the Illinois Democrat wielded influence through backroom diplomacy, deep legislative knowledge, and procedural fluency—not base-pleasing bombast.
That kind of power is harder to come by in a Washington shaped by Trump-era spectacle.
How we got here: Durbin was first elected to the House in 1982 before winning his Senate seat in 1996.
He has served as Senate Democratic whip since 2005, making him the longest-serving Democratic whip in Senate history.
As chair of the Senate Judiciary Committee, he oversaw the confirmation of Justice Ketanji Brown Jackson—part of a record 235 federal judges confirmed during Biden’s first term.
Looking ahead: Durbin’s retirement opens the door to a high-stakes primary to succeed him.
Illinois Lt. Gov. Juliana Stratton announced her campaign this morning.
Reps. Lauren Underwood, Raja Krishnamoorthi, Robin Kelly, and Sean Casten, which could have a ripple effect on the House Democrats’ quest to win back the majority next November.
The whip race is also on:
Sen. Brian Schatz (D-Hawaii), Durbin’s current deputy, and Sen. Amy Klobuchar (D-Minn.), the number three Senate Democrat and ranking member of the Senate Agriculture Committee, are seen as frontrunners.
Sen. Sheldon Whitehouse (D-R.I.) is expected to succeed Durbin as chair of the Senate Judiciary Committee.
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The great Democratic handoff
Durbin’s decision to step down after more than four decades in Congress didn’t just shake up the Senate—it added fresh momentum to a slow but unmistakable turnover at the top of the Democratic Party.
Allow me to explain: His announcement follows a string of high-profile departures that began when former Speaker Nancy Pelosi (D-Calif.) and her top two deputies stepped down from House leadership in 2022.
Less than two years later, former President Joe Biden opted against seeking a second term, instead throwing his weight behind Kamala Harris.
And now, reports suggest Rep. Jan Schakowsky—another longtime Illinois Democrat—plans to retire early next month.
Looking ahead: Progressives see an opening to push for more turnover—and a new generation of leadership.
Activists are urging aging senators like Jack Reed (D-R.I.) and Ed Markey (D-Mass.) to follow Durbin’s lead.
Their argument: Democrats can’t build a party of the future with a leadership class stuck in the past.
And while Schumer faces fewer open calls to step aside, frustration is simmering.
Grassroots discontent has grown since Schumer advanced a GOP-led funding bill last month to avoid a shutdown.
That tension could resurface ahead of the 2026 midterms—and especially if Schumer decides to run for a sixth term in 2028.
Want to reach the people shaping policy and politics? Once Upon a Hill puts your message in front of the Capitol’s most plugged-in audience—where influence meets insight. Let’s talk about how a sponsorship can align with your goals. Email michael@onceuponahill.com to learn more.
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Democrats escalate oversight of Trump deportations
Several Hill Democrats traveled this week to spotlight what they describe as the human and constitutional costs of President Trump’s immigration agenda.
Allow me to explain: In El Salvador, Reps. Maxwell Frost (D-Fla.), Robert Garcia (D-Calif.), Yassamin Ansari (D-Ariz.) and Maxine Dexter (D-Ore.) advocated for Kilmar Abrego Garcia, a Maryland resident who was deported despite a Supreme Court order protecting him from removal.
Meanwhile, Reps. Ayanna Pressley (D-Mass.), McGovern, Bennie Thompson (D-Miss.), and Troy Carter (D-La.), along with Sen. Markey, visited two ICE detention facilities in Louisiana to meet with Rümeysa Öztürk, a Tufts University Ph.D. student, and Mahmoud Khalil, a Columbia University graduate.
Both Öztürk and Khalil have been detained for more than a month without criminal charges, allegedly due to their pro-Palestinian activism.
What they’re saying: Frost accused the Trump administration of arresting, detaining, and deporting individuals without due process—the principle that people have a right to challenge the evidence against them before the government takes away their liberty.
“We must hold the administration accountable for these illegal acts and demand Kilmar’s release,” Representative Frost said. “Today it’s him, tomorrow it could be anyone else.”
Pressley delivered a similar warning from Louisiana.
“We’re in Louisiana to demand answers, shine a light on this damning violation of their constitutional rights, and call for their immediate release,” she said. “Our destinies are tied, and we will not allow these abuses of power to go unchecked.”
How we got here: The Trump administration is executing a sweeping deportation campaign that includes both undocumented immigrants and some lawful residents.
The administration is invoking the 1798 Alien Enemies Act and the 1807 Insurrection Act to facilitate the rapid removal of individuals, including those with pending asylum claims.
Though officials acknowledged Abrego Garcia’s deportation as an “administrative error,” they have refused to comply with the court’s directive to facilitate his return.
The El Salvador delegation proceeded after House Republican committee chairs denied requests to authorize it as an official congressional delegation.
The visit followed Sen. Chris Van Hollen’s (D-Md.) meeting with Abrego Garcia last week, which drew national attention to the administration’s noncompliance with court orders.
Masked officers detained Öztürk without warning in March. ICE agents arrested Khalil at his university-owned apartment in Manhattan.
Pressley, Markey, and Senator Elizabeth Warren (D-Mass.) led a letter last month signed by over 30 lawmakers demanding information from senior Trump officials about Öztürk’s detention and similar cases.
In the know: The Salvadoran government denied the lawmakers’ request to meet with Abrego Garcia, prompting demands for daily proof-of-life updates and his immediate return to the U.S.
Frost said the impression he received from the local U.S. embassy was that the Trump administration has made no effort to facilitate Abrego Garcia’s return to America.
The lawmakers also requested proof of life for Andry Hernández Romero, a 31-year-old gay Venezuelan asylum seeker detained in the notorious CECOT prison since being deported in March. No one has heard from him since March 14.
Pressley met directly with both Öztürk and Khalil during the Louisiana visit.
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Trump’s approval hits new low as economic backlash builds
A new Fox News poll released this week found President Donald Trump’s overall job approval has dropped to 44 percent—his lowest since returning to office. His rating on the economy, the very issue many voters cited as a reason for electing him, has sunk to a new low of 38 percent.
Allow me to explain: The slide comes as the administration doubles down on erratic tariff policies, igniting a new trade war that’s rattled markets and strained supply chains.
Add to that the resumption of student loan payments next month and growing anxiety over potential cuts to Social Security, SNAP, and Medicaid in the still-unreleased GOP reconciliation bill, and a clear political backlash is beginning to take shape.
Together, these economic stressors undercut Trump’s central promise that he alone could deliver prosperity. For now, the numbers suggest voters aren’t buying it.
What they’re saying: Democrats seized on the poll results.
“I'm sure it pained FoxNews to finally have to report the truth,” a House Democrat told Once Upon a Hill. “This administration has been disastrous for the American people in every way.”
Schumer said it took less than 100 days for President Trump to lose the country's confidence.
“His chaotic, ill-conceived and poorly executed policies are leaving American families dazed and confused and with less money in their pockets,” he added. “This erratic behavior is hurting Americans on Main Street and on Wall Street, hammering their pocket books and their retirement accounts. The more Donald Trump does, the more American people don’t like what they see.”
By the numbers: Trump’s approval is now the lowest of any president at this point in office in a quarter century.
George W. Bush: 63 percent
Barack Obama: 62 percent
Trump (first term): 45 percent
Joe Biden: 54 percent
Not so fast: Border security is the only issue where voters give Trump positive marks, according to the same poll.
But that reality illustrates why his administration has leaned so heavily into its mass deportation campaign.
With his economic numbers slipping and overall approval underwater, Trump appears to be doubling down on the one area where his message still resonates—despite growing legal, moral, and humanitarian backlash.