Richard and Elizabeth Uihlein have been fighting for more than a decade to roll back Obama-era restrictions on the hours that long-haul truckers can work. Since 2014, their Wisconsin-based business-supply company, Uline, has spent $870,000 on lobbyists registered to push for a reversal of policies that Elizabeth Uihlein has said cause “increased inefficiencies and expense.” As the fourth-biggest disclosed donor to conservative and Republican groups in the 2024 election cycle, their views carried some weight.After incremental erosion of the restrictions during President Trump’s first term, the latest victory came last summer, when Secretary of Transportation Sean Duffy announced two pilot programs to allow truck drivers greater flexibility in the hours they work. “We’re getting Washington out of your trucks and your business,” Duffy said when he announced the change in June.But Duffy was also working on a side project. Four months later, he transferred $1 million from the dormant campaign committee that had funded his congressional races in Wisconsin to a new group, called Northwoods Future PAC. The next month, Richard Uihlein became the only other donor to Northwoods, giving $1 million, according to public filings. As of the end of last year, Northwoods Future PAC had spent nearly $1.2 million on mailers and television ads to promote Duffy’s son-in-law, Michael Alfonso, who is running for the congressional seat previously held by the Cabinet secretary. The ads cast Alfonso, a 26-year-old who recently moved to the Duffy family home after working on a podcast in Florida, as a “working-class fighter” who would crusade against insider political machinations. “Time and time again, Washington politicians get rich,” one Northwoods ad for Alfonso begins, “while Wisconsin gets ignored.”The donation is just one example of how Duffy has maintained unusual relationships with representatives of the companies he regulates. In December, the secretary was listed as a “special guest” at a campaign event for Alfonso that was sponsored by transportation lobbyists, including those for Delta Air Lines and BNSF Railway, a decision that former ethics advisers to Presidents George W. Bush, Obama, and Biden told me they would not not have allowed or would have tried to reverse. Duffy has also embraced President Trump’s call to use corporate money, sometimes from companies that have transportation interests, to promote efforts by the department to celebrate America’s 250th anniversary.Duffy’s advisers deny any quid pro quo or impropriety, and say all of his actions have been cleared by ethics advisers at the Transportation Department who are not political appointees. “Regulatory decisions are guided by career safety professionals, the law, and the facts,” the Transportation Department spokesperson Nathaniel Sizemore told me. Duffy supported revisions to the “Hours of Service” trucking rule for years before he took his current job, and the president issued an executive order a year ago calling for the removal of “needless regulatory burdens” in the trucking industry. Uline, the company the Uihleins control, did not respond to a request for comment.The arrangements have nonetheless raised alarm. Zach Cahalan, the executive director of the Truck Safety Coalition, told me that Richard Uihlein’s involvement with Northwoods created “clear conflict of interest concerns” for Duffy. Richard Painter, who was Bush’s chief ethics lawyer and is now registered as an independent, says he tried to stop administration officials from appearing at events hosted by federal lobbyists, even though such arrangements are technically allowed federal rules if the officials do not use their titles, solicit funds, or engage in any official business. (Duffy’s title did not appear on the event invitation, which also said he was “not soliciting” funds at the event.) “I would tell him to stay the heck away from this thing. It’s going to embarrass the president,” Painter told me about Duffy’s involvement in a lobbyist-sponsored event for his son-in-law. “It just gets too dang close to circumstantial evidence of quid pro quo.”But the ethics practices that steered past administrations have eroded in Trump’s Washington. The shift has given lobbyists and corporate interests new opportunities to perhaps win favor with regulators by supporting their chosen causes—and it appears to have given those regulators new opportunities to take on projects that their predecessors avoided.As recently as 2012, Obama refused donations from registered lobbyists, and his campaign announced that he would not appear at events for super PACs that supported him. During the Biden administration, two former ethics officials told me, there was a White House policy that prevented Cabinet secretaries from appearing at events hosted by lobbyists with business before their departments. During the first Trump term, the Department of Transportation’s inspector general referred for possible criminal prosecution findings about then-Secretary Elaine Chao’s use of department resources to help her family’s global shipping company. The Department of Justice, in the final weeks of Trump’s first term, declined to prosecute.Though the Trump administration has long been less strict about ethics rules than its predecessors, despite the president campaigning on a promise to “drain the swamp,” the second term has been even more freewheeling. Trump has fired or demoted more than 20 inspectors general, including the official responsible for the report on Chao. He has aggressively raised money from companies, lobbyists, and trade groups seeking his favor to fund projects such as his presidential library and a super PAC for the coming midterm elections, and the construction of a new ballroom at the White House and a memorial arch on the Potomac River. Trump has kept careful track of the money coming in, calling his top fundraiser late at night for updates—and monitoring who is giving, who is not, and the role of lobbyists who bundle donations. The president has also urged his Cabinet secretaries to help fundraise for costly celebrations this summer for the nation’s 250th anniversary, events that depend on extensive financial partnerships between federal officials and companies that seek their favor.[Read: Trump’s eye-popping postelection windfall]Duffy has thrown himself and his department into those preparations. Last May, he announced the Great American Road Trip, a Department of Transportation initiative to get Americans out on the nation’s roads this summer. Shortly after, Tori Barnes, a recent lobbyist for the U.S. Travel Association who previously worked in government relations for General Motors, founded a nonprofit called The Great American Road Trip, Inc., using the same logo that Duffy had unveiled outside his department’s headquarters. The nonprofit does not disclose donations, but its website lists several “sponsors” that are regulated by Duffy, including Toyota, Boeing, Royal Caribbean Group, the American Bus Association, and CRH, a company that provides building materials for publicly funded roads. Weeks later, the department lent its name to a new mobile-phone app, built by General Motors, called Explore250, which suggests places to visit by car and allows users to collect digital stamps commemorating their travels.Duffy embraced the nonprofit last month and provided a quote for the group’s news release: “Join us on this exciting adventure.” A spokesperson for the Department of Transportation said Duffy is working with the nonprofit and other public-private 250th-celebration efforts in his official capacity, as part of an administration-wide effort. Barnes told me that Duffy “has absolutely nothing to do” with the nonprofit’s fundraising efforts. She added: “That is solely my responsibility.”Painter said he believes government officials should avoid association with outside nonprofits or companies while in office. He objected to Biden’s decision to allow the Penn Biden Center (now Penn Washington) at the University of Pennsylvania and the Joseph R. Biden School of Public Policy and Administration at the University of Delaware to continue to use the president’s name while he served in office. “We do not endorse nonprofits or for-profits with the seal of approval of the United States government,” he said. “I don’t care how patriotic it is.”The White House spokesperson Kush Desai, in response to this story, described Duffy as “a critical asset for President Trump and his administration,” specifically praising the secretary for “spearheading celebratory events for America’s 250th birthday.”Duffy has taken a more direct approach to supporting his son-in-law’s campaign, a decision that has caused tension with White House advisers. Alfonso, who previously worked in construction and for Dan Bongino’s podcast, is married to Duffy’s eldest daughter, Evita.On November 11, six days before Uihlein gave his donation to Northwoods, Duffy traveled to Wausau, Wisconsin, to appear at a meet-and-greet for Alfonso. He also was listed as a “special guest” for a December 3 fundraiser for the campaign. An invite to that event, previously reported by Politico, listed the Delta Air Lines PAC as a host, along with a group of Washington lobbyists with interests before the Department of Transportation or past ties to Duffy. They included Husein Cumber, who represents eight companies on lobbying efforts at the department; Andy Keiser, who represents BNSF Railway; and Tyler Duvall, the president of the smart-highway company Cavnue. Eight employees of the lobbying firm BGR Group, which represents Delta and is where Duffy previously worked, were also listed as hosts. (Duffy decided last year to terminate a joint venture between Delta and the Mexican carrier Aeromexico, a major setback for the companies, amid an ongoing dispute over U.S. carrier access to Mexican airports.) Duffy ultimately did not attend the event, because a White House announcement with Trump happened at the same time, two people familiar with the planning told me.But Alfonso’s campaign has since benefited from donations from lobbyists and transportation-industry PACs. These included donations from fundraising efforts affiliated with Delta Air Lines, the National Air Transportation Association, General Motors, Lockheed Martin, the U.S. Travel Association, and Brightline Holdings, a privately owned passenger-train company. Other lobbyists not listed as hosts with business before the department have also since given to Alfonso’s campaign, ProPublica recently reported.Sizemore said that career ethics officials at the Department of Transportation “reviewed and cleared” Duffy to appear at the Alfonso event hosted by lobbyists. “These processes and rules have existed for decades,” Sizemore told me. “If Secretary Duffy attends fundraising events, he does so in his personal capacity and he will continue to do so.”[Read: Fox News vets are taking over America’s 250th birthday party]But two ethics officials who worked for the Biden administration, who requested anonymity because of their current jobs, told me that such an arrangement would not have been permitted when Biden was president. In advance of the 2024 reelection campaign, the Biden White House set up a system for screening and approving any party or candidate fundraisers that Cabinet secretaries attended in their personal capacity. “On the hosts, we would not allow anyone to be from a regulated industry or a lobbying firm,” said a former ethics official in the Biden White House Counsel’s office, who was involved in vetting fundraisers.A second former senior political appointee in the Department of Transportation general counsel’s office also told me that the secretary would not have been permitted to be listed as a speaker at a fundraiser hosted by industry lobbyists. “We would not have wanted to put the secretary in that position,” this person said. “We wanted there to be a clear line.”Norm Eisen, a White House special counsel for ethics during the Obama presidency who has since helped lead legal efforts against the Trump administration in federal courts, told me that Duffy’s decision to attend a lobbyist-hosted event for his son-in-law would not have passed muster during the Obama years because, he said, “it creates the appearance of possible beholdenness to special interests.”The lines in more recent weeks have been anything but clear, as Duffy has rolled out more public-private partnerships to celebrate the nation’s anniversary. On March 6, Duffy appeared at Union Station in Washington to announce a new Department of Transportation advertising campaign, funded largely by private industry. Several private companies had agreed to wrap their vehicles or display advertising celebrating the nation’s birthday at the request of the department and Freedom 250, a fundraising effort set up by Trump’s advisers. Acting as host, Duffy introduced executives from Brightline, Penske, and Greyhound-owner Flix. “We have public assets, public property,” Duffy told the group. “But we have so many partners from around industry and corporations that want to celebrate in this great birthday.”