Commerce Secretary Howard Lutnick went on CNBC this fall to promote a deal so great that he deemed it “off the rails.” The government of Japan, he explained, had brought down its tariff rate by giving President Donald Trump $550 billion to spend on whatever he wants. “They are going to give America money when we ask for it to build the projects,” he said with a grin.The president himself had been describing the agreement similarly—and was dismayed to later learn that the billionaire businessman turned bureaucrat, his longtime friend, had misunderstood the terms.Japanese leaders—who typically favor quiet diplomacy—made clear that they had not given Trump the blank check that Lutnick described. They would have a say in how the money was invested, and maintained the right to reject proposals. Making matters worse, the Trump administration had initially increased tariffs on Japan in August, during the rollout of the broader deal, an error that its chief negotiator described as “extremely regrettable.” Taro Kono, a member of Japan’s House of Representatives, told reporters that month, as the confusion was playing out in public: “Washington is just randomly shooting, and they are shooting some like-minded countries from behind.”Trump was irritated by public skepticism over the agreement’s terms, as were top White House aides, five officials with direct knowledge of the discussions told us. “Howard is telling the president things that just aren’t true,” a Trump confidant said, referencing the Japan deal. “You just can’t do that.” A senior administration official clarified that Trump’s “ire wasn’t just directed at Howard, but also at the Japanese negotiators.” The White House declined to comment on the miscommunication.It was not the first Lutnick blunder to frustrate the president, White House officials and others told us. We talked with more than a dozen people familiar with Lutnick’s approach, who all requested to speak anonymously so as not to anger Lutnick or the president. They say that the commerce secretary—a key player in executing the president’s economic agenda—lacked a basic understanding of his negotiations with foreign trade partners, held up deals, berated allies, and openly bickered with other members of Trump’s team. One administration official told us that Lutnick “will actively move the goalposts with foreign countries days after Trump says we have a deal.” Another described him as the “bottleneck” among the president’s economic advisers because “he doesn’t understand the issues” and is a micromanager relying on a small group of advisers who don’t help him learn.And there are growing worries within Trump’s inner circle that activities at Lutnick’s former company, now run by his sons, could ethically, financially, or legally compromise him as a member of the Cabinet. (The White House told us that Lutnick has completely divested from his business interests and adheres to ethics requirements. The Commerce Department added that he will continue to do so.) Top White House officials have expressed their concerns about some of these issues directly to Lutnick.Yet the commerce secretary is still in his position. Part of the reason is the president is trying to avoid the Cabinet shake-ups that were a defining feature of his first administration, one person in Trump’s inner circle explained to us. But Lutnick is also the president’s trusted friend who is executing a key campaign promise—negotiating reciprocal trade deals—that many within the administration view as the highest-stakes portfolio for the country and, ultimately, the president’s legacy. For all his stumbles on the details, Lutnick shares Trump’s overarching belief in the utility of tariffs, something that few of his peers in the financial world can say—and he isn’t afraid to take a hard-knuckle approach, even with allies. Jason Miller, a longtime aide to the president, summed it up to us this way: “The president has never criticized or admonished or sought to rein in someone on trade matters, because that’s one of the core philosophical planks of his administration.” The low point for Lutnick may have come last month following comments he made about Jeffrey Epstein, which some thought would surely end his government career. In a video interview with the New York Post, he recalled living next door to Epstein’s Upper East Side mansion, stopping by for a tour with his wife, and quickly leaving after the billionaire financier showed off the massage table in the middle of his house. “In the six to eight steps it takes to get from his house to my house, my wife and I decided that I will never be in the room with that disgusting person ever again,” Lutnick said. His claim that Epstein’s creepiness was obvious called into question efforts by the White House to assert that Trump couldn’t have known that Epstein, his former friend, was a sexual predator who abused young girls. Lutnick also suggested that Epstein probably had recordings of many of his associates who’d gotten massages at his home, calling the late convict the “greatest blackmailer ever.”The interview made the president and his top aides “go nuclear,” another Trump confidant told us, because it brought renewed attention to an issue that the White House has been trying to bury amid bipartisan calls for greater transparency. Even some of Trump’s most devoted backers have demanded that the Justice Department turn over what it knows about the identities of Epstein’s high-profile clients.[Read: Inside the White House’s Epstein strategy]Since then, even in Trump’s far more disciplined and discreet second term, it has become especially easy to find officials and other Trump allies willing to criticize Lutnick. (“You’re not going to believe what he said to the Japanese!” a U.S. official recently told us. We happened to mention Lutnick’s name in passing at a recent meeting to discuss military operations and were surprised when another official started venting about a mistake the secretary allegedly made involving Brazil. In a different meeting, with a top administration official, the mere mention of Lutnick made the official visibly, if almost involuntarily, flinch.) Even those who spoke well of Lutnick described him as “unorthodox,” a “character,” or “a bit intense.”Nearly everyone we spoke with conceded that Lutnick still holds sway with the president, the most valuable asset in this administration. The White House spokesperson Kush Desai didn’t answer specific questions about Lutnick but in a statement called him an “invaluable member of the Trump administration” and said he played a “key role securing historic trade deals with Japan, the EU, and South Korea.” He added that Lutnick “has been one of the President’s most forceful advocates.”The Commerce Department, responding to questions about this story, highlighted the secretary’s record in delivering “major trade deals for the American people” and advancing the president’s “America First trade agenda.”Like many in Trump’s second administration, Lutnick has no previous government experience. As a former CEO of Cantor Fitzgerald, a financial-services firm, Lutnick is accustomed to making decisions based on his own instincts, not the input of others. Even with the Trump administration’s lax approach to bureaucratic processes, his style makes for an awkward fit with a senior government role.The bond between Lutnick and Trump was forged from tragedy. On September 11, 2001, 658 of Lutnick’s Cantor Fitzgerald colleagues, including his 36-year-old brother, perished in the World Trade Center’s North Tower. Lutnick’s life was spared because he was taking his son to his first day of kindergarten that morning. He sobbed on national television, endearing himself to a nation in mourning. Cantor Fitzgerald, like most of Wall Street, resumed its work two days after the attacks—and for five years, it paid a quarter of its profits to the families of the workers who were killed. It also covered their health care for 10 years.Lutnick and Trump had long known each other from the New York City rubber-chicken charity-dinner circuit, although they weren’t particularly close at the time. As Lutnick described it, they would often hit the town together when events wrapped. “We chased the same girls, okay?” Lutnick told the All-In DC podcast in March. After Cantor Fitzgerald was decimated by 9/11, Trump reached out to Lutnick more frequently to check on him and offer support. Lutnick appeared on Trump’s reality show, The Apprentice, and their relationship deepened. Lutnick said Trump “still tortures me” for donating to Hillary Clinton, whom he got to know after 9/11 when she was a senator. “He’s just sassing me, okay? Because I gave him tons of dough. He knows I love him.”That love for Trump continued after the January 6, 2021, Capitol riot, when many former backers distanced themselves from the president. In 2023, Lutnick’s lifelong indifference to politics took a turn when Trump called him asking for help. “I gave him 10 million bucks right then and there,” Lutnick told All-In DC. He went on to raise an additional $75 million for Trump by leaning on his Wall Street connections. “Steve Witkoff and I, we arm wrestle for who’s the best friend of the president in the administration,” Lutnick told NewsNation in September, referring to Trump’s envoy for the Middle East and Russia.“Lutnick offers two things that President Trump values most—loyalty and money,” a confidant to both Lutnick and Trump told us. (The donor list for Trump’s new White House ballroom includes the Lutnick family.) Another took a less charitable view of their relationship, complaining that Lutnick has a tendency to linger near Trump and “invites himself everywhere.”[Read: Nancy Walecki’s quest to find the East Wing rubble]Late last year, Trump tapped Lutnick to help build his second administration, with a focus on personnel selections and vetting. Lutnick credits himself for recruiting Elon Musk and coining the name of the Musk-led Department of Government Efficiency, or DOGE. (After Musk’s exit, Lutnick told Axios that Musk got it “backwards” and should have first focused on cutting spending and waste, not mass firings.) Lutnick prides himself on being someone Trump trusts, whom the president can use as a sounding board for some of his most offbeat ideas—like annexing the Panama Canal. Earlier this year, the two men also conjured up a “gold card” that would grant legal residency to wealthy foreigners for $5 million.Lutnick had angled to become Trump’s Treasury secretary, a role that ultimately went to another wealthy hedge funder, Scott Bessent. Multiple people told us that Lutnick still wants the job. “Trump wouldn’t do it, and everyone would make it their sole mission in life to prevent that from happening, and it would be a disaster,” another person who knows both men told us. “The Treasury secretary has to project calm, stable competence, and Howard is the furthest thing from calm, stable, competence.”A person close to Lutnick told us he doesn’t want the role and is “very happy” serving as commerce secretary.Sometimes, Lutnick’s cavalier style has made him a target for criticism, even for things that are not entirely his fault, a U.S. official told us. In April, Trump unveiled a universal 10 percent import tax—an event he dubbed “Liberation Day”—in retaliation for what he has long said are unfair trade barriers on U.S. products. The tariffs were so sweeping and hasty that a group of barren, uninhabited volcanic islands near Antarctica that are home to glaciers and penguins was among their targets. It was “clearly a mistake,” Australia’s trade minister, Don Farrell, told the Australian Broadcasting Corporation at the time, underscoring a “rushed process” by the United States.“That was Lutnick,” one administration official told us, eager to blame him for the error. The U.S. official countered that the Commerce Department was not responsible for producing the data that slapped the Heard and McDonald Islands with tariffs. But Lutnick, ever the cheerleader for the president’s priorities, defended punishing the poor penguins, telling CBS it was meant to close the “ridiculous loopholes” in trade.Lutnick is among the most outspoken disciples of Trump’s aggressive trade strategy, which is controversial even within his own party. Many Republican lawmakers worry that his tariffs on allies and foes alike are inflicting economic pain on the average American. (A Federal Reserve report in October confirmed that tariffs are pushing inflation generally higher as companies are caught between absorbing the costs and passing them on to customers.) At Trump’s boisterous Madison Square Garden rally just days before last year’s general election, Lutnick, who shouted his remarks to the point that his voice cracked, argued that America’s heyday was at the turn of the 20th century, when the country had tariffs and no income tax. [Read: “I run the country and the world”]The Commerce Department is sometimes referred to as the broom closet of the federal bureaucracy because of the vast—and unrelated—functions that it oversees. That portfolio includes both promoting economic growth through creating jobs and monitoring trade, and overseeing the Census Bureau and the National Weather Service.But according to several U.S. and foreign officials, Lutnick assumed the role with a significant deficit in his grasp of trade, how to negotiate with foreign partners, and how to execute the president’s agenda. “He doesn’t understand tone, diplomacy, or even what he told the same country a few weeks prior,” one administration official, who has sat in several meetings with Lutnick, told us. “Many countries have come and said they don’t know how to engage Lutnick, since he seems unsure of his position week to week.”Multiple officials detailed episodes with foreign counterparts that underscored some of Lutnick’s broader shortcomings—but most of the countries involved in the episodes they detailed were eager to praise him on the record when we gave them the chance. Three officials told us that Japanese leaders have expressed a desire to deal with Bessent, the Treasury secretary, who is less likely, in their view, to throw negotiations into disarray. (A senior Japanese official told us that Bessent was the original negotiator in their trade talks, but when he became busy working on the president’s One Big Beautiful Bill Act, Lutnick took over, and they welcomed his involvement. Japan’s top trade negotiator, Ryosei Akazawa, told us that working with Lutnick is the “greatest pleasure.”) Lutnick threatened Canadian negotiators with tariffs, but wasn’t able to provide details as to which goods would be targeted, leaving Canadian negotiators stumped as to how to proceed, officials with knowledge of the exchange told us. (Those negotiations fell apart last month, after Trump was triggered by an anti-tariff television ad from a Canadian province that aired in the U.S. during the World Series.) The Canadian government declined to comment.[Read: The Elon Musk and Scott Bessent shouting match]And Lutnick berated European Union officials over the bloc’s stance on trade, an approach that one European official described as “hostile” and uninformed. Lutnick later resumed discussions with a more receptive tone when Trump decided he wanted a deal with the EU. (Another top European official disputed this characterization of their talks, while a top U.S. official conceded that Lutnick can sometimes “come in hot, but he means well.”) The European Commission’s lead trade negotiator, Björn Seibert, told us his talks with the Trump administration were “by no means easy,” but he said Lutnick played a “constructive role.” The United Kingdom’s top negotiator, Varun Chandra, said Lutnick is “tough” but “direct and fair as a counterpart.”Lutnick’s allies say he’s not trying to please everyone. “The president chose him because he knew Howard wouldn’t take their bullshit,” the confidant of both men told us. “Sometimes you have to piss people off to get deals done.”