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Loose Lips Can Sink Careers

White House South Lawn.
photo by Mark Skrobola

There are a lot of jobs that demand discretion. People who hold such jobs must maintain confidences despite all sorts of pressure to share important or merely juicy information.

Doctors, lawyers, therapists, clergy and tax preparers have legal and professional standards that demand they respect confidentiality in all but very limited situations. Detectives and journalists promise anonymity to sources regularly. The former tend to receive more leeway from supervisors and prosecutors; the latter have, on many occasions, gone to jail rather than reveal a source. Spouses are generally immune from being forced to inform or testify against one another, although whether they invoke that immunity may depend on the couple’s relationship.

In the workplace, departments such as legal, accounting, payroll and human resources deal with sensitive information all the time. So do senior executives, as well as those executives’ personal assistants, who often see every scrap of text before it reaches their bosses. That is why the job was once sometimes known as a “private secretary.” Anyone who has ever held such a position has either understood – or quickly been informed – that discretion is an essential element of the job.

If you are the executive assistant to the president of the United States of America, the need for discretion is especially strong. An entire room full of journalists right down the hall would gladly trade almost any body part for a smidgeon of your knowledge.

In an alcohol-lubricated interlude of an hour or so, Madeleine Westerhout forgot these facts of life. She paid for it with her job.

The basics have been widely reported. While President Trump was vacationing at his golf resort in Bedminster, New Jersey, Westerhout went out to dinner at a nearby restaurant with four journalists and a White House deputy press secretary, Hogan Gidley. At some point, Gidley needed to step away for an interview with Fox News. He left the 28-year-old Westerhout alone with reporters Phil Rucker of The Washington Post, Jennifer Jacobs of Bloomberg, Steve Holland of Reuters and Andrew Restuccia of The Wall Street Journal.

The dinner was supposed to be “off the record.” In the strictest sense – the way I learned to understand the term in journalism school in the 1970s – that means that, as far as the rest of the world is concerned, the “off-the-record” conversation between reporter and source never happened. This goes beyond a mere promise of confidentiality to the source. It means the reporter cannot use the information at all, unless he or she later acquires it elsewhere.

By this strict definition, an off-the-record group dinner is a contradiction in terms. How can two people pretend they never spoke when four other people witnessed the conversation? That this sort of event was considered off the record at all reflects the slovenly habits of modern journalists and many of the people who train them. Gidley, who should have known better than to bring Westerhout to dinner and then leave her alone, has a degree in broadcast journalism from the University of Mississippi.

This sort of social interaction between Washington journalists and White House staff, or (in bygone days) even presidents themselves, used to be kept private under a much less formal “gentleman’s agreement” (with due respect to the late United Press International correspondent Helen Thomas). The public’s business was understood to be fair game, but family and personal matters were off-limits. Journalists held back what they knew about Franklin Roosevelt’s health and John F. Kennedy’s extramarital dalliances. But whatever boundaries existed vanished long ago with the reporting about a presidential candidate named Gary Hart and a yacht aptly named the Monkey Business. Today, anything goes.

So Gidley left Westerhout alone with four reporters who, while presumably willing to preserve their own professional confidences, would have been hell-bent on inducing her to break hers. The liquor undoubtedly helped, as did Westerhout’s youth and inexperience. She is certainly old enough and professionally accomplished enough to be held to adult standards, but people her age still benefit from mentors and are often vulnerable to sharks.

Westerhout did not betray any national security secrets, or tip off the reporters to some important legislative or political agenda. She merely gossiped and bragged. She reportedly said Trump avoids being photographed with his daughter Tiffany because of her weight. Westerhout further claimed that she had a better relationship with her boss than he has with his daughters Tiffany, who is a private citizen, and Ivanka, who is a prominent White House aide. That assertion was doubtful at best, but before she lost her job, Westerhout was widely known as the gatekeeper to Trump. The president himself told journalist Bob Woodward that she was “the key” to gaining access to him.

The first the public heard about this conversation-that-never-happened was last week, when Westerhout abruptly left her White House position. It has been variously reported that she resigned, was forced out or was fired by Trump, although the president declined to characterize it that way. It is a distinction without a difference. Once her comments became known, even if only to Trump, Westerhout’s continued presence in such a sensitive job was untenable. He knew it. She knew it. Anyone with any business or political experience would have known it.

So how did Trump find out about her comments? He said Westerhout told him about the conversation herself. It is possible that she did so unprompted, out of a feeling of guilt or remorse. It is also possible, and I suspect more likely, that Westerhout’s comments became the object of scuttlebutt in the White House press corps, much like the infamous Steele dossier that was shopped to multiple outlets before BuzzFeed put it on the record and the rest of the media passengers climbed aboard that trolley.

Arthur Schwartz, a conservative commentator, claimed on Twitter that Rucker was the one who “burned” Westerhout by revealing the off-the-record conversation. Rucker declined to comment. His supervisor, Washington Post national editor Steven Ginsberg, said in an emailed statement reported by outlets including Politico and Slate that Rucker “has never violated Washington Post standards or policies.”

I entirely accept this weasel-worded explanation, which avoids saying whether Rucker disclosed Westerhout’s comments-that-never-happened to anyone who wasn’t present at the off-the-record dinner. It speaks, instead, to the changes in the newspaper’s standards and policies.

When Woodward was a Washington Post general assignment reporter, and for decades after, he refused to identify his famous “Deep Throat” Watergate source to anyone other than his reporting partner, Carl Bernstein. Deep Throat was only confirmed to be former FBI Deputy Director Mark Felt in 2005, 31 years after President Richard Nixon resigned as a result of the Watergate scandal. In their Watergate reporting, Woodward and Bernstein never used any information from Deep Throat until they had obtained it elsewhere. And they never discussed what Felt told Woodward with anyone else, although they wrote about his statements anonymously in their book “All the President’s Men.”

If one of my daughters had held Westerhout’s White House position, and she told me she planned to go to dinner with four journalists and a White House press spokesman, I would have asked why she was going. In her position, what good could come of this dinner and the accompanying conversation? I might have suggested she dine instead with a colleague or a college friend. Or that she go to a yoga class, or maybe travel to nearby New York City and enjoy a Broadway performance of “Come From Away.” The knives are sharp in Washington these days, and Westerhout would have looked like a lamb chop to the reporters at that dinner table.

While some may hold her error against her (and the internet never forgets), I believe Westerhout will be fine in the end. Trump himself said on Twitter that he had forgiven her and called her “a very good person” who “had a bad night.” It would not shock me if at some point she finds another job in his administration or re-election campaign, or in the family-controlled Trump Organization after he leaves office. Many other managers would look at her as an unusually accomplished young woman who likely learned some valuable lessons from this experience. Her professional life, at 28, is far from over.

As I said, many jobs demand discretion. But jobs are held by humans, and humans make mistakes. Westerhout’s lapse tells us nothing that we did not already know about her, or about Trump, or about life and media in Washington today.

Larry M. Elkin is the founder and president of Palisades Hudson, and is based out of Palisades Hudson’s Fort Lauderdale, Florida headquarters. He wrote several of the chapters in the firm’s most recent book, The High Achiever’s Guide To Wealth. His contributions include Chapter 1, “Anyone Can Achieve Wealth,” and Chapter 19, “Assisting Aging Parents.” Larry was also among the authors of the firm’s previous book, Looking Ahead: Life, Family, Wealth and Business After 55.

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