In a meeting last July about the new administration’s objectives in Afghanistan, President Trump turned to his national security advisers and suggested they arrange a series of lunches for him with enlisted military personnel who had served overseas.

“The president made an analogy to a restaurant that he goes to," said a senior White House official who was there at the discussions, "and he said that the guys who owned it hired some big-name consultants, told them what to do, renovated it … and it basically was a flop. He said, ‘All they needed to do was ask the waiters.’ His point was, sometimes when you really want to know what to do, you don’t go to the senior guys with the high price tags, you ask the people who are closest to the problem.”

Two weeks after that meeting, the White House communications team awoke to a series of humiliating headlines.

“Trump compared Afghanistan War to 21 Club Renovation,” read an article by New York Magazine, followed by a headline in Slate accusing the president of likening the war “to when his favorite restaurant closed for renovations.”

“Somebody leaked that anecdote to make him look bad,” the senior White House official told the Washington Examiner, accusing the culprit of “deliberately missing [Trump’s] point.”

Leaks of sensitive, classified, or just plain gossipy details have eroded morale and often contributed to chaos inside the West Wing, sometimes sparking political firestorms that eclipse the president’s agenda for days or weeks at a time.

For example, a report detailing a phone conversation between the president and Australian Prime Minister Malcolm Turnbull caught the White House off guard in January 2017. Aides were forced to defend the erratic behavior Trump had exhibited during the early diplomatic encounter when anonymous “U.S. officials” leaked the contents of the call to the Washington Post. The documents cited claimed that the president blasted Turnbull over a refugee resettlement deal struck by former President Barack Obama, called the phone call the “worst” of several he had made that day, and abruptly ended the conversation.

Months later, the Post released transcripts of the contentious phone call, along with another one between Trump and Mexican President Enrique Peña Nieto. In the latter conversation, the president acknowledged he was in “a little bit of a political bind” after repeatedly promising his supporters that Mexico would pay for the construction of a border wall.

“Those two [leaks] were bad in that these are documents that are classified,” said the senior White House official. “They are deliberative documents that show the president in direct deliberation or negotiation with foreign leaders … and I don’t think [that] had ever happened before.”

Measures taken since then, especially by the White House's new chief of staff, have successfully plugged some of the leaks. But as the last few weeks have shown, the administration is still far from waterproof.

Classified leaks, potential crimes

The White House has struggled to overcome two kinds of leaks, both of which have caused problems for a press shop that often struggles to get out of a defensive crouch.

Leaks of sensitive or potentially classified information have not only created distractions for a White House team that has an agenda to promote. They've also raised questions about whether administration officials committed crimes in publicizing things that had happened behind closed doors.

White House aides found themselves struggling to counter the leak of a private diplomatic conversation Trump had botched after the president in May met Russia's foreign minister and Sergey Kislyak, then Moscow's ambassador to Washington. “Current and former U.S. officials” accused the president in another leak to the Washington Post of divulging highly classified information to the Russians, jeopardizing intelligence sources in the process.

H.R. McMaster, Trump’s national security adviser, said he was in the Oval Office for the meeting with the Russians, and he denied to reporters that Trump revealed any classified information. But the reports fueled speculation that Trump and his administration were too friendly with Russia when the president was already fending off allegations of having fired FBI Director James Comey the previous week, at a time when he was overseeing an investigation into Russia's meddling into the 2016 election.

Former CIA Director John Brennan said at the time that the leak was “very, very damaging” and described the apparent revelation to the media of classified information about Trump’s conversation with the Russians as “appalling.”

White House officials took steps to limit the availability of sensitive information after Trump’s conversation with Kislyak leaked to the press. Chief among the changes was limiting the access of the president’s aides, so they had information relevant only to their own policy portfolios or roles, one White House official said.

The Trump administration is known to have successfully charged just one person, a former contractor named Reality Winner, for unauthorized disclosure of classified information. Winner was accused in June of sharing a document about Russian hacking with The Intercept, a news organization. This crime could put her behind bars for years if she is convicted.

Attorney General Jeff Sessions told Congress in November that the Justice Department has opened 27 investigations into classified leaks. Decrying the “epidemic proportions” of leaks under Trump, Sessions noted that the Obama administration opened just nine leak investigations in the preceding three years.

A Justice Department spokeswoman told the Washington Examiner that she had “no updates” about whether the number of leak probes has changed since last year.

Obama took heat during his second term for the aggressive tactics his Justice Department used to pursue leak cases, including secretly spying on reporters’ phone records and emails, and even naming a Fox News reporter as a co-conspirator in a leak probe.

Mark Zaid, a longtime national security attorney, said he hasn’t seen any evidence that Trump has gone after leakers more aggressively than his predecessors. Zaid once represented Jeffrey Sterling, the former CIA operative convicted under the Obama administration of leaking classified information to James Risen of the New York Times, in a discrimination case against the CIA, and has handled dozens of cases involving whistleblowers and journalists who published leaks.

“I haven’t seen much of anything that has happened beyond what you would say is completely normal in any administration,” Zaid said.

Zaid noted the number of open leak investigations, though higher than under Obama, did not guarantee that the Trump Justice Department would crack down.

“I would caution as to how significant that is because it really depends on what kind of leaks we’re talking about," he said. “Oftentimes, the vast majority of these leak investigations go nowhere, and so even if there’s a higher number that are open, it doesn’t necessarily mean anything.”

The process of investigating a classified leak, Zaid said, begins with the creation of a list of people who may have known whatever details made their way into the news.

“As these leak investigations take root, the agencies have to look at, first of all, how many people have authorized access to the information? There’s lots of people who generally have access, so they have to start narrowing that down.”

Zaid cited a leak in February 2017 about former national security adviser Michael Flynn’s conversations with Kislyak, describing the disclosure as “absolutely illegal” because it came from intelligence reports the government created using surveillance. He said the starting point for a potential investigation into the Flynn leak would involve a wide circle of officials who may have handled intelligence related to the ousted national security adviser.

“A lot of people would have known about the fact, assuming it to be true, that Flynn had conversations with Kislyak,” Zaid said. “All the lawyers who worked on the FISA application, the agents, the court staff, members on [Capitol] Hill, people in the White House.”

Trump has long fixated on the disclosure of sensitive information to reporters from people inside his administration, and he has encouraged his attorney general to take a harder line against those who spill secrets.

“The spotlight has finally been put on the low-life leakers! They will be caught!” he tweeted in February of last year, as controversy raged over Flynn’s leaked conversations with the Russian ambassador.

A week later, Trump complained that the FBI had been “totally unable to stop the national security ‘leakers’ that have permeated our government for a long time.” The president then returned to social media in April to demand that someone “find the leakers,” whose disclosures he described as the “real story” plaguing his White House.

Embarrassing leaks and gossip

A series of staff departures — including former chief of staff Reince Priebus and former chief strategist Steve Bannon — and the arrival of a new chief of staff have stemmed but not eliminated the kind of embarrassing, salacious leaks that characterized many stories in the first half of Trump's presidency so far. (AP Photo)

A second type of leak has dogged the West Wing with more frequency and aggression than classified leaks, however. Particularly in the early months of the Trump presidency, White House aides often fought to solidify their positions internally by leaking stories about their rivals to the media.

The constant coverage of power struggles, warring factions, and personal feuds dominated much of the conversation about the Trump White House in the first half of 2017.

A series of staff departures — including former chief of staff Reince Priebus and former chief strategist Steve Bannon — and the arrival of chief of staff John Kelly have stemmed but not eliminated the kind of embarrassing, salacious leaks that characterized many stories in the first half of Trump's presidency so far.

“General Kelly has instilled a sense of discipline and order since coming on board," said veteran GOP strategist Ron Bonjean. "Before his arrival, there seemed to be an effort by some allies of the president or potentially individual staffers to use leaking as a way of influencing Trump on policy and personnel decisions.

"This effort has largely quieted down for now because there is a well-supervised process for how information and context is delivered to Trump in an orderly way," Bonjean added.

By tightening the president’s schedule, keeping a hawk-like watch over the information Trump consumes, and monitoring who enters or exits the Oval Office, Kelly has often been able to prevent leaks from occurring or to determine the sources when they did, although the process has not been foolproof. His methods were later supplemented by a personal cellphone ban throughout the West Wing.

White House press secretary Sarah Sanders claimed the move was intended to “protect White House information technology infrastructure from compromise,” but the timing of it, amid the release of lurid excerpts from Michael Wolff’s tell-all book about the Trump administration, led most reporters to suspect otherwise.

Staff turnover may have also helped, as the White House faced a cascade of senior-level departures between July and December of last year. Among them was Trump’s scrappy chief strategist, Bannon, a fast-talking adviser who was rumored to have a select group of reporters constantly cycling in and out of his West Wing office.

Like several of his colleagues, Bannon was seen as belonging to a group of top aides who used eager reporters to influence decision-making or knife their opponents through headlines.

Take, for instance, Bannon’s removal from the National Security Council last April, which the White House eventually confirmed had occurred during a reshuffling that elevated military officials to more senior roles. Days later, an unnamed “senior administration official” told Politico that friends had to convince Bannon to stay put in the West Wing after the NSC episode. Some reporters on the Trump beat suspected the tip came from Trump’s son-in-law Jared Kushner, a New York native who regularly clashed with Bannon and often pushed the president to reject his chief strategist’s nationalist approach.

The political leaks had become so bad by the time Anthony Scaramucci was hired as White House communications director last July that the outspoken investment banker made it his sole mission to root out all the administration’s loose lips.

“I’m going to fire everybody. That’s how I’m going to do it,” Scaramucci said during his brief tenure at the helm of the White House press shop. “You’re either going to stop leaking, or you’re going to be fired.”

Ironically, Scaramucci himself prompted the resignation of Michael Short, an assistant White House press secretary whom he suspected of leaking, after disclosing that he was going to fire Short during an interview with Politico. Scaramucci later criticized the outlet for “leaking” the plan he had openly described to its reporters.

Yet, even after Kelly's arrival and the staff turnover, the Trump White House remains leaky by historical standards. In recent weeks, there were reports that the president considered firing Russia special counsel Robert Mueller and administration lawyers expressing skepticism about Trump submitting to a Mueller interview. There have been rumors of tension between Trump and Kelly, with the president reportedly disliking his chief of staff contradicting campaign pledges during immigration negotiations. There have even been stories alleging Trump marital discord. And just last week, White House sources claimed Kelly knew well in advance about assault allegations against Rob Porter, who resigned as Trump's staff secretary on Wednesday.

White House deliberations about a controversial memo prepared by House Intelligence Committee Republicans appeared in print. Trump was quoted in the press telling former FBI Deputy Director Andrew McCabe to ask his wife what it felt like to be a loser. Many of these unflattering stories clearly came from people at the White House.

The biggest issue with leaks, according to sources inside the White House, is that most of the embarrassing information making its way to print is the product of “carelessness” on behalf of one or several individuals, making it harder to determine the source and whether the leak was deliberate.

“You can’t refer something to the Justice Department unless you have reason to believe a crime has been committed. So, if it looks like classified information was divulged, you can refer it, [but] if it’s just a gossipy leak to make someone look bad, it’s not a crime, unfortunately,” the senior administration official said, noting that the latter happens all too often.

“Let’s say you’re in a meeting with 10 or 12 people, and somebody in that meeting goes and tells one of their senior colleagues what happened because they think it’s important that they know, and that senior colleague tells somebody else who happens to tell it to a reporter,” the official explained. “That’s a leak, in that it was information that was not contained where it should have been, but it wasn’t intentional. Stuff just got out because people just didn’t take as much care as they should have.”

Asked whether any methods of prevention have been discussed, the official said, “You can’t stop people from talking about what they heard at meetings.”