The White House Press Corps Needs To Think Like Lawyers


​I just watched the latest Trump press conference. As usual, it was a disaster. Not for him so much, as he’s apparently bulletproof and/or oblivious, but for things like rationality, democracy and civil society. It served as just the latest in a never ending series of reminders that  we have given a dangerously arrogant, deluded and incompetent man the nuclear codes.

It also reminded us that the press has no idea how to ask Trump a question.

I understand why they are having so much trouble. While presidents have used press conferences as a means of propaganda and reality denial for as long as presidents have given press conferences, at least a small amount of actual information has been disseminated at the things over the years.  Presidents — even Nixon — have always possessed at least a scintilla of shame which regulated just how big their lies could be and which, in turn, reined in their most nonsensical tactics of distraction. As such, a reporter’s lazy, open-ended or compound question has never been that harmful.  Presidents have become experts at ducking them and steering them to other, more comfortable topics, but they have always at least pretended to be acquainted with reality and have always communicated some rudimentary information as they sparred with the Fourth Estate.

Not Trump. He hits the lectern at Mach 2 with his hair on fire spewing a brand of nonsensical drivel that would make Tristian Tzara chuck it all, go back to school and become an actuary. He is so utterly shameless that, were he not so mendacious, dangerous and corrupt, it’d almost be perversely admirable. He has blown past Orwellian archetypes so quickly that he is not even bothering to answer the question “what is two plus two” with “five.” He’s gone straight on to “potato.”

As such, the presidential press conference has shed the last vestiges of an exchange of information and has, necessarily, become a truly adversarial affair. The guy being questioned has already, in explicit terms, declared war on the press. The investigative journalists and columnists have grokked this and are firing their big guns at Trump on the daily. It’s time for the members of the White House Press Corps — the ones who actually get to ask Trump questions — to quit pretending they’re sparring and join the goddamn fight.

While I am a member of the media, I’m not really a reporter. I never went to J-school and I don’t interview people very often. I don’t have a fedora with a card that says “press” in the band. I don’t even own one of those cool little digital tape recorders. As an interviewer of willing, sensible and amiable subjects, I’m fairly mediocre. I get the basic information fairly well, but I’m not fantastic at digging too deeply below the surface. I just don’t have the reps yet.

But as a lawyer who did cross-examinations and depositions and who conducted internal investigations for 11 years, I do have a lot of experience asking questions of people who don’t want to answer them. Or who have something to hide. Like any trial lawyer, I’ve sat across a table or stood across a room from people who I knew to be lying to me and I got them to either admit it or to look so bad in denying it that they may as well have.

I was not successful at it because I am uniquely talented. Indeed, compared to my colleagues, I suspect I was pretty average when it came to legal talent and instincts. I was successful at it because I followed some basic rules that I and every other trial lawyer is taught. They are rules that, in this mad age, when the President of the United States of America is trying to get one over on us like some employee embezzling from the payroll of my clients tried to get over on me, would serve the White House Press Corps well.

The big ones:

  • Your questions should be tight. They should be limited to one fact per question. The more complicated a question or the more loaded it is with facts, the more easily Trump can quibble with it or deny it. Indeed, if you load it up with premises, sub-premises or multiple parts, Trump can quite fairly deny or evade the question based on a premise, a fact or a sub-part that is technically incorrect. Don’t give this guy that opportunity. Leave out the extraneous stuff and ask a single question.
  • If Trump won’t directly answer your question, repeat your question. Do not rephrase it. Do not allow him to move on from it. Repeat it verbatim, slowing down and pausing between words if necessary, like you might do to your five-year-old. Eventually, even as he continues to evade your simple, tight question, he will begin to look obstructionist or ridiculous. And yes, I realize that a lawyer can do this all day because he or she is the only one asking the questions and that the president may move on to another reporter. In that case, collude with your fellow reporters and agree that if one of you is ignored, the next one called upon will ask the question. I know you’re competing with each other and everything, but you all get to go write your own story later and no one will care who asked the question. You have bigger fish to fry here.
  • Do not try to “win” the exchange with one crushing blow. In court, witnesses do not break down in tearful confession like they might in some movie. They answer a series of basic and often innocuous questions at the end of which, if you’ve done your work properly, their credibility and their story is in tatters. Similarly, Trump will never admit, in response to any one question, that he is wrong or that he’s lying. But he may very well answer a dozen questions which serve, in the aggregate, to paint him as wrong and paint him as a liar. You may not get your Will McAvoy-style “Ah ha!” moment out of such questions, but it doesn’t matter. Save that stuff for the story you write after those questions or the news report you anchor. Those are your closing arguments in which you explain, based on the evidence presented, what happened in that press room.
  • Do not get hostile or personal and do not get distracted. While I characterized this as a war, your means of attack is not a full frontal assault. Think of it as a war of attrition. Your simple, tight questions constitute your offensive and your persistence in demanding that they be answered your defensive perimeter or naval blockade. In court, or in depositions, witnesses often try to turn things back around on the lawyer or the lawyer’s client, reacting in a hostile manner. A good lawyer never takes that bait. they just continue to ask the questions they want to ask. Likewise, Trump tries to turn every press conference into a referendum on the media, trying to disrupt your questioning by making it all about you. Don’t bite. The mission of the press is not to justify the work of the press and a presidential press conference is not a place to defend your ego. If he wants to attack the media he can do it on Twitter. No reporter should be enabling him to do so at a press conference.

Litigation, war and conducting presidential press conferences are, obviously, very different things. But they do have a few things in common. In all three you have a mission. Thanks to the approach the Trump Administration has taken, in all three you, unfortunately, have an adversary. Above all else in all three you have to have a plan and it has to be a plan that you can carry out without your adversary controlling the terms of engagement. By following the rules of litigation and, in some cases the rules of war, you’re way more likely to be successful than whatever the hell it is you’re doing now.

Craig Calcaterra

Craig is the author of the daily baseball (and other things) newsletter, Cup of Coffee. He writes about other things at He lives in New Albany, Ohio with his wife, two kids, and many cats.