What is the role of a general in a democracy? Many of today’s military leaders have a very particular answer: Focus on tactics, carry out orders, and otherwise shut up.This is not what America’s top officers have always done. The country’s most senior generals and admirals are expected to provide unvarnished military counsel to the president and swear an oath to defend the Constitution. History is full of examples of officers who also spoke up about the ethics and strategic implications of the president’s choices. But with a commander in chief who has stated that he prefers “the sort of generals that Hitler had,” and a secretary of defense who has fired top officers for exhibiting insufficient loyalty, military leaders during the Trump presidency have defined their advisory role extremely narrowly.Dan Caine, the general whom President Trump plucked out of retirement—and obscurity—to serve as chairman of the Joint Chiefs of Staff, has come to personify that circumspect approach. He presents military options and addresses tactical and force-related matters, but avoids big-picture questions of geopolitics and the probity of the administration’s actions, provided the administration deems them legal. Other top officers have followed his example.Caine articulated his stance to the graduates of the National Defense University last month. The future top ranks, he said, must be clear about the limits of their role when they advise senior leaders about the risks and benefits of potential operations. Can we go do this? is a military question, Caine told the officers sweltering in their dress uniforms, one “that the joint force answers.” But “the should we? question lands at the policy level, and we don’t do that in our business,” he said.Seen one way, Caine’s studious deference to civilian authority is an appropriate correction from the generals in charge of America’s wars in Iraq and Afghanistan, who were famously strident about what they thought the wars should be about and how they should be run. Top officers such as Caine serve at the pleasure of the president and can be relieved anytime; their jobs are to provide military counsel, not to shape preferred outcomes.But looked at another way, Caine and other generals are being overly timid and deferential, in part because Pete Hegseth demands it. The secretary of defense has forced out more than 20 generals and admirals, including some of the most respected career officers in the forces: Caine’s predecessor, Air Force General C. Q. Brown Jr.; two other members of the Joint Chiefs; and, most recently, Army General C. D. Donahue. Meanwhile, Hegseth has promoted less experienced officers. He has offered no explanation for each individual ouster, and the dismissals have fed a sense among his senior commanders that he prizes fealty and acquiescence over competence and experience.[Read: An Army shake-up in the middle of a war]Assertive generals, too, can offer bad advice. The Afghanistan and Iraq wars, led by more outspoken military leaders, dragged on, cost trillions of dollars, and ended far short of victory. Yet the Iran war, led by more reticent brass, hasn’t achieved the administration’s stated objectives, either. Before the conflict started, commanders had crafted a contingency plan for the U.S. military to keep shipping moving through the Strait of Hormuz, which called for additional ships, troops, and other forces in anticipation that Tehran might attempt to close it. But the president chose a different course. Commanders faithfully executed the president’s guidance and were careful not to criticize it publicly, only to see Iran close the strait to commercial traffic, disrupting global commerce and prompting the Trump administration to agree to a tenuous cease-fire and a (thus far futile) return to diplomacy.All of which raises the question: How should the American public expect generals to behave?The answer is made urgent by how Trump himself views the military. In his first term, Trump berated his Pentagon leaders as “dopes and babies”; after leaving office, he accused his chief military adviser of treason. In his second term, egged on by Hegseth, Trump has sent troops into U.S. cities and used the military for his legally dubious campaign against suspected drug traffickers in the Caribbean. He has also mused about deploying the military to monitor elections. That makes the balance that military leaders must strike—between deference to civilian leaders and their duty to the Constitution and the force they represent—an even thornier challenge. “If Trump 1.0 was the Olympic Games for these military leaders,” Carrie Lee, a scholar who specializes in civil-military issues at the German Marshall Fund of the United States, a think tank, told us, “then Trump 2.0 is The Hunger Games.”Questions about how the military and its elected leaders should interact are older than the United States. General George Washington weighed in on policy with the Continental Congress during the Revolutionary War, repeatedly arguing that he did not have sufficient resources to defeat the British. When his pleas were rebuffed, he continued to advise the congress while adapting to what his civilian leaders wanted, with the goal of preserving the Continental Army. After victory, Washington famously resigned his military commission in 1783, before he became president.One of the country’s most successful examples of civilian-military partnership came decades later, when President Abraham Lincoln gave General Ulysses S. Grant broad operational latitude to lead Union forces in the Civil War and Grant accepted Lincoln’s authority to set the conflict’s political objectives.Perhaps the greatest civilian-military controversy erupted in 1951 when President Harry Truman fired General Douglas MacArthur for publicly challenging the administration’s approach to the Korean War. The president’s decision to remove one of the nation’s most celebrated (if outspoken) generals preserved the chain of command, even though many people believed that MacArthur had legitimate concerns about Truman’s “limited war” strategy, which aimed to prevent escalation. Truman publicly explained his reasons for that decision, letting the rest of the force know what civilian leaders expected of them. (Historians generally agree that MacArthur, venerated battlefield leader though he was, had gone too far.)This administration has been unique for its lack of transparency over why generals are ousted. And in the run-up to the war in Iran, there was no chance to hear from the generals and admirals who would lead that war. Americans heard much more forthright rationales from generals involved in the wars in Afghanistan and Iraq.[Listen: The military Pete Hegseth wants]Before the 2003 Iraq invasion, General Eric Shinseki told members of Congress that he believed “something on the order of several hundred thousand soldiers” would be needed to occupy the country, an assessment that then–Defense Secretary Donald Rumsfeld rejected. General David Petraeus later made the case for surging forces into Iraq in a bid to take on a burgeoning insurgency. In that era, Petraeus and General Stanley McChrystal were nationally known figures who expounded on grand strategy, held forth with the media, and rallied the public around policies the military supported in ways that some civilian leaders believed was out of line.When Joe Biden was vice president, he blamed generals such as McChrystal for attempting to “box in” President Obama on Afghanistan and force him into approving a massive troop increase. Obama wrote in his memoir that, as the Afghanistan debate came to a head, Biden leaned in close to the president’s face and told him: “Don’t let them jam you!” The White House wanted the Pentagon, officers joked darkly, to “shut up and color,” like a kindergartener. (When Biden became president, he selected Lloyd Austin, a low-profile former general unlikely to challenge the White House, as his Pentagon chief.)Many officers treat The Soldier and the State, by the political scientist Samuel Huntington, as their civil-military bible. The 1957 book advocates for civilian leaders to exercise “objective control” over a battle-hardened professional military class that remains apart from politics. But the most astute recognize the folly of the notion that the military can sidestep politics entirely. Particularly at the three- and four-star level, officers may refrain from engaging in partisan rhetoric and events, but they operate in the political realm, dealing with budgets, lawmakers, and the media.America’s founders feared a military powerful enough to threaten democracy, so they vested ultimate authority in civilians. But they premised that system on the assumption that those civilians would use their power responsibly and with congressional oversight. During the first Trump administration, Pentagon leaders pushed back on the president’s most egregious proposals. In 2020, Joint Chiefs Chairman Mark Milley was horrified when Trump suggested shooting unarmed protesters and deploying the military to police American streets. He and other Pentagon leaders worked behind the scenes to ensure a successful transition of power following the president’s 2020 defeat.Milley, a voluble Army general whom Trump hand-picked as military chief, epitomizes the assertive and politically confident officer, as comfortable with opinion makers and foreign leaders as he is with the average grunt. But some current and former officers we spoke with believe that Milley overstepped at times—for example, when he spoke in support of studying critical race theory before Congress, providing fodder for right-wing complaints about a woke military; or when he took what many saw as a veiled shot at Trump as a “wanna-be dictator” in his 2023 retirement speech. (Milley became such a bête noire for Trump that Biden, fearing the general would be prosecuted when Trump returned to power, gave Milley a preemptive pardon.)[From the November 2023 issue: How Mark Milley held the line ]Many of those same officers, who spoke on the condition of anonymity because of the sensitivity of the subject matter, now believe that Caine and others are overcorrecting for Milley’s approach, especially in the face of Hegseth’s stifling of dissent and his campaign to remake the military according to his vision of a hypermasculine, ultra-loyal force. The pendulum, these officers believe, has now swung back too far.Kori Schake, a defense analyst and a contributing writer for The Atlantic who has also written a book about U.S. civil-military relations, told us that Hegseth’s unexplained ousters, combined with a lack of public or congressional debate before military action in Iran, Venezuela, and the Caribbean, “have created a command climate that penalizes the honest evaluations of the military about issues on which the military is expert and the civilians are not.” Vladimir Putin’s cowed generals fostered the erroneous belief the Kremlin could score an easy victory in Ukraine; U.S. generals, Schake added, shouldn’t have the same fear of speaking up. “That’s very dangerous,” she said. “That’s how you lose wars.”Caine is known as an even-tempered, assiduous officer; he is awake by 3 a.m. and on his first call by 4:30. In his office hang images of the Stoic philosopher Marcus Aurelius, General George C. Marshall (a fellow Virginia Military Institute graduate), and the compound where U.S. forces hunted down the Islamic State leader Abu Bakr al-Baghdadi. Caine has become one of Trump’s closest aides, particularly because the president relies on just a small coterie of national-security advisers. During his first 365 days on the job, Caine made more than 330 trips to the White House.Caine’s White House conversations remain private. His approach is “speaking truth to power, privately,” one person familiar with his thinking told us. But speaking before Congress and the press, he has repeatedly ducked questions about the wisdom of Trump’s controversial initiatives, including the deployment of National Guard troops in majority Democrat cities and the decision to launch a war with Iran without congressional or public debate.[Read: Trump’s new favorite general]Caine has often cited classified information or his need to “maintain trust” with his civilian bosses, among others, to explain why he won’t publicly give even general assessments about major aspects of the war. Asked by Senator Dick Durbin, a Democrat from Illinois, during one hearing whether Operation Epic Fury, the code name for the Iran war, had achieved its goals, Caine replied: “Sir, only political leaders decide victory or defeat, and I’ll leave it to them to opine on that.” Detractors say that his background may explain some of his approach: Unlike past chairmen, Caine had not previously served at the four-star level, where officers gain valuable political experience, or headed a large command.Some officers have been more forthright. General Gregory Guillot, the head of Northern Command, acknowledged to lawmakers that it would be illegal to place armed troops at polling places except in the case of an armed rebellion, even though the president has suggested he might do just that.But other senior officers have followed Caine’s tight-lipped lead, careful not to seem at odds with their bosses. Early in the Iran war, Hegseth declared that America would provide “no quarter” to its enemies. The military’s own rules prohibit such orders or statements because they imply leaving no survivors on the battlefield or executing prisoners of war. In a congressional hearing in May, Representative Jason Crow, a Colorado Democrat and former Army Ranger, asked Admiral Brad Cooper, the head of U.S. Central Command, to affirm that the Law of War Manual prohibited such a declaration. “It’s clear from a U.S. military perspective, we follow the law of armed conflict,” Cooper demurred. He was trying not to enter the political fray by sparring with Democrats frustrated with Hegseth’s comments, one of his defenders told us. But what message was he sending to the troops he oversees? Crow was incensed. “You’re a combatant commander. You’re one of our most senior military officers with tens of thousands of service members under your command,” Crow said. “This is not leadership to not be able to say something as basic.”At the same hearing in May, Cooper answered another question the way Hegseth might have—by punching back. Representative Seth Moulton, a Marine veteran, pointed out to Cooper that the Iran war wasn’t meeting its objectives. “I would like to know how many more Americans we have to ask to die for this mistake. Do you know?” Moulton, a Democrat, demanded. Cooper, perhaps because of Moulton’s reference to fallen troops, was visibly furious. “It’s an entirely inappropriate statement from you, sir,” Cooper shot back.In our combined decades of covering Pentagon leaders testifying before Congress, neither of us had ever seen a military leader push back against an elected official so forcefully. Officers, no matter how much they might resent congressional grandstanding, are supposed to sit there and take it. That’s part of the job.Cooper requested a follow-up conversation with Moulton after that hearing. The two men later huddled, in an encounter that hasn’t previously been reported. Cooper was still riled, people familiar with the exchange told us, and told Moulton that his remarks had crossed a line; he believed that the congressman, as a veteran, should have risen above politics. Moulton responded that he likewise thought Cooper had been political and had failed to sufficiently answer lawmakers’ questions. The two men shook hands before parting ways.[Read: Hegseth, Rubio, and Caine had an auto-deleting Signal chat]For a general who says he is not political, Caine briefly embraced an administration talking point on a key—and hotly disputed—element of the Iran conflict: What constitutes a broken cease-fire? Caine told reporters in May that Iran’s repeated firing at commercial ships, despite Trump’s declared cease-fire, fell “below the threshold of restarting major combat operations at this point,” a seemingly political judgment. But he quickly reined himself in. When asked what constituted “major combat operations,” Caine said that such assessments were “above my pay grade.”Many people inside the Pentagon and on Capitol Hill have wondered whether Caine and other senior officers are hoarding their influence with Hegseth and Trump for when they really need it—during a constitutional crisis, for instance, such as an attempt to place troops at polling stations in 2026 or 2028. (Caine is due to step down in September 2027, but he may be extended.) Caine and other officers have promised to follow the law. But they are operating in an administration that has been willing to act first and litigate later.History remembers both Washington and Marshall less for their tactical brilliance than for their strategic leadership. They astutely navigated the politics of their times, and their legacies were shaped not only by what they did in uniform but by the institutions they left behind. Caine and today’s other senior brass may ultimately be remembered for their choices about when to quietly defer to civilian leadership—and when the moment demands they speak up.