Since his first day in office, Donald Trump has been testing the boundaries of the law on multiple fronts. From his open hostility towards the investigation into his campaign’s involvement with a foreign adversary, to his policy prescriptions by way of executive order, to the way Donald Trump runs his own White House this president has challenged the rule of law like no other recent president. So, in the case of Donald Trump v. the Law — who’s winning? And what can we learn from what’s happened so far?
In this episode Chris gets answers from Kate Shaw, a law professor from the Cardozo School of Law who has worked in both the White House, the Supreme Court and who happens to be his wife. It was also her birthday on the day this was recorded — `and yes, that came up.
CHRIS HAYES: It just seems like there's a fundamental cultural tension between the way you do things in that environment and being the president of the United States when you have to take care the laws are faithfully executed and be surrounded by lawyers and dot i's and cross t's.
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KATE SHAW: Maybe it is the case that when you come up in this private sector background in particular sort of this New York kind of real estate background. You view yourself as constrained, maybe, only by the kind of outer bounds of what you can get away with.
CHRIS HAYES: Welcome to "Why Is This Happening?" with me, your host, Chris Hayes. So you watch our show, "All In" on MSNBC, recently, you notice, probably, that we have a lot of lawyers on the show. Every night we have three or four different lawyers with different legal backgrounds and experiences. The reason we have so many lawyers is that one the central stories right now is the law and the president. The president versus the law, the president's relationship to the law and really deep profound, almost, I don't know, existential question about the rule of law in America in the age of Donald Trump. In the end, who is going to win. Donald Trump or the law. That's how I feel a lot. And this president is someone who has such a fascinating relationship to the law. Because at one level, there's no one who's spent more time around lawyers then Donald Trump. I mean the guy has been sued and sued hundreds and hundreds of time.
CHRIS HAYES: He has used the law to his great advantage, he has used the law as kind of weapon or a tool wielded to exert his power and his leverage. He understands the law as a thing that can be useful to him, not as binding constraint. And then he took that view of the law and he became the most powerful person in the world in the American constitutional system. Where the law really matters and he still has this kind of flagrant disregard for it. He has this aggressive lawlessness, and the lawlessness cascades down throughout his entire administration and the way that he conducts policy and the way that he writes executive orders and the way he conducts himself personally. And when you look around, you see him bumping up the against the law, fighting with the law, the law trying to fight back. Exert its control, the sort of wrestling match that plays out in front of us.
CHRIS HAYES: Whether it's Robert Mueller or it's the courts or it's the Department of Justice, between this president and the law. And there's one person who I want to talk about that topic with the most. And this person is to me, the person who best embodies everything that is great about the law. She's a lawyer, she's a law professor, she clerked for Judge Richard Posner, who's a legendary appellate judge in the seventh circuit in Illinois. She clerked for Justice John Paul Stevens on the Supreme Court. She then was an associate White House counsel under Barack Obama for several years. She is a law professor at Cardozo School of Law here in New York, she's also a consultant for ABC and a contributor where she does Supreme Court coverage and analysis for them. She's also my wife. Her name's Kate Shaw, she is my wife and my life partner and the love of life and we met when we were 19, and I'm 39 now and we've been together in our lives longer than we have not been together.
CHRIS HAYES: So I get basically all of my legal knowledge and fascination with the law and insights into the law all through osmosis. Basically all from Kate. I completely coast off of her expertise and brilliance and all that she knows about the law. I wanted to bring her in because she embodies all the things that Donald Trump seems to be a rejection of. She also has incredible insights in two different ways about the law, which is that practical experience, she has worked in a White House, she knows what it's like to vet people, she knows what it's like to work on the Supreme Court, she knows what it's like to work on a Supreme Court opinion. And also theoretical, she thinks about constitutional law, she thinks about the way that the president's speech interacts with the law. And I just thought, if there's one person in the whole world I want to talk to about the law at this moment, the rule of law in the era of Donald Trump, it is my wife, Kate Shaw.
KATE SHAW: Somewhere I need to say that I have not heard anything you said to introduce me and so I'm not cosigning it, I just haven't had a chance to veto it. No, only 'cause I'm sure it's gonna be some overstated recitation of resume of the greatest lawyer who ever lived which is-
CHRIS HAYES: You are the greatest lawyer of your generation.
KATE SHAW: I'm just saying, I'm not cosigning-
CHRIS HAYES: I genuinely believe you're the greatest lawyer of your generation.
KATE SHAW: Well, you should believe that about your spouse, so thank you.
CHRIS HAYES: I objectively believe that. There's lots of external reasons to believe that, it's not just like some fantastical belief of mine.
KATE SHAW: It's ridiculous.
CHRIS HAYES: No, it's not ridiculous. Let me start with this, why I wanted to have you on. Guess you're wondering why you're here. By the way, it's happy birthday.
KATE SHAW: Thank you. This is like our version of calling into "Fox & Friends" on your spouse's birthday, confessing you didn't get a present.
CHRIS HAYES: Really nice card, I think is what he said. Yeah, it's awesome to have you here. Joshua just said to me, Joshua Chaffee, he's a senior producer on the show, said to me that like, so often in editorial meetings throughout the day, and segment meetings, I'm always like, "Oh well, Kate says this, Kate says that. Kate makes this point about the law, Kate has this really great point that she made to me this morning. I wish we could have Kate on this segment. If Kate were here she would say ..." So you're like this sort of spectral ... I'm not making this up, 100%. So I thought, well, instead of referring to you, I could actually bring the embodied version of you onto the podcast here because you won't come on the television show.
CHRIS HAYES: I'm always thinking of you because both you are and how you think about the law, how deeply felt it is for you, but also that you worked in the White House and the White House counsel's office as associate counsel, you clerked in the Supreme Court Justice John Paul Stevens, you've been around very high stakes legal matters and have been there. Been on the front lines of making these determinations. I guess maybe the best place to start is just like, when you take a step back and you survey the amount of legal peril that both the president personally is and also as the president, it just seems like he's gotta lot of legal problems, is that wrong? He does, right?
KATE SHAW: Yes, I think there are definitely a lot of legal problems, a lot of legal peril. Sorry, I'm gonna turn my phone off. I feel like I should maybe keep on it, since all parents are now in this studio. If our children need us, someone should be listening. But all right, I'll turn the phone off.
CHRIS HAYES: Oh, they'll be fine.
KATE SHAW: They'll be fine.
CHRIS HAYES: Your parents are podcasting, some day we will explain it to them.
KATE SHAW: It’s normal, it’s totally normal.
CHRIS HAYES: When they're old enough, we'll explain what podcasting is.
KATE SHAW: All families do this.
CHRIS HAYES: When two people love each very much, they get in front of microphones and headphones and then a podcast is born. Okay.
KATE SHAW: What if we did this every night, it would be so weird. Okay, so I think in terms of legal jeopardy that the president is facing, I think we can break it down into a few different categories. First, sort of all the successful legal challenges to president's substantive policy initiatives. So that is kind of one category. And that's the DACA rescission, the travel ban, some of what he's done in the environmental sphere. The Supreme Court hasn't ultimately weighed in on this, but he has run into a lot of roadblocks in the lower courts in trying to implement a lot of these policy initiatives. So that's sort of first category of legal trouble or legal jeopardy.
CHRIS HAYES: Like stuff he's doing as president. Like, I wanna ban people from these countries or I want to take away DACA and the court's being like, not so fast.
KATE SHAW: Right, a lot of people would say that's the system sort of operating as it should if his staff members in the White House in cabinet agencies, are just taking lots of risks and shortcuts and there's a lot of kind of reckless sloppy policy making happening. But that's sort of one category I would say of kind of legal trouble. The second one maybe would be, investigations into staff members and I think that includes both White House staff and cabinet members. So whether that's ethics issues or F.B.I. background investigation issues, the Hatch Act, political activity. So I'd say that's kind of the second category of legal trouble or legal jeopardy that feels like they're constantly enmeshed in. And then the third, is kind of more the president's personal legal exposure. So the Russia affairs, obviously the kind of center of that Mueller investigations.
CHRIS HAYES: We cover that sometimes on the show, we'll do a segment here or there on the Russia situation.
KATE SHAW: It just feels like it's moving at warp speed so I don't know exactly when you're going to put these podcasts out but I don't even know if there's that much to say about it today that's gonna be all that relevant in two weeks or a month.
CHRIS HAYES: For all we know this will be in a post-pee tape world in which these people are going to IMAX showings of the thing but the time this thing comes out, 'cause who knows.
KATE SHAW: It does feel like it's moving fast.
CHRIS HAYES: Although, it feels like it's both moving fast and also there's like a treadmill quality to it. It's like ever accelerating and also staying in the same place, same time, somehow. So you've got these three categories which I think is a good way of thinking about it.
KATE SHAW: Just kind of legal exposure, legal jeopardy in the White House, yeah.
CHRIS HAYES: So the stuff he's trying to do, the stuff around staff and cabinet officials, and then the president. It's the last thing that we talk about the most on the show, but maybe let's talk about the first thing. Which in some ways for consequences of people in the world and the country is the biggest. It seems to me that he's had a tough climb in the courts. Particularly on these big signature things like DACA and the travel ban. Why do you think that is?
KATE SHAW: Sloppiness and recklessness, I would say are kind of at the heart of both. They've just done a really bad job of dotting i's and crossing t's and just actually implementing these things in really basic ways the way government conduct has to occur. So take the travel ban, the first executive order, so we're now in the third iteration of the travel ban. So the first one is issued a week after the administration begins and it's clear that there's been no process whatsoever that predates the issuants of that executive order. So typically when the executive branch in general rolls out a major new policy, it does it after extensive consultation with the relevant executive cabinet agencies. It's convened usually weeks and months and sometimes obviously these processes can feel excessive. But there's a lot of subject matter expertise in the federal government.
KATE SHAW: And so you want to bring in with a policy like this, Department of Justice, Department of Homeland Security, the State Department, the Defense Department, the Intelligence community, you want to sort of run a robust inter-agency process that would result in a series of recommendations that president would adopt. There would be notifications given, you'd also have a communications roll-out strategy. You'd put calls out together with reporters who cover this stuff and sort of explain how the policy is gonna work. You'd put out guidelines to the field, so that on the ground officials in airports and embassies and consulates understand the policy change. And none of that happened. So literally, an executive order was issued and nobody understood anything about how this policy was supposed to work.
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KATE SHAW: Because in addition to kind of all these process failures, it just contained some real drafting errors or ambiguities. It wasn't all clear from the face of the order whether green card holders who happened to be abroad when the order was issued could even re-enter the country. Ultimately, the White House counsel ended up issuing a memorandum that purported to clarify the green card holders weren't supposed to be covered.
CHRIS HAYES: Even that though, that detail always struck me as so, okay so the White House counsel just writes a memo and it's like, what the heck is the legal status of that document.
KATE SHAW: Right. And that's what the Ninth Circuit basically said, there's no real authority for the idea that the White House counsel can through a memo, amend an executive order and he probably he can't. They don't usually try but ... So that's an example of kind of the policy failures but also just the document itself reflected this kind of rushed and sloppy and careless policy development process. Courts struck it down, fast and hard and eventually the administration decided just to stop fighting for it and withdraw it and replace it with another executive order. They've tried to run a more robust process, so a year and a half into the administration, they were taking sort of more care in following processes, I would say. Much more than sort of in the first week.
CHRIS HAYES: To me, the sloppiness there, it's endemic. And this relates to something ... Part of the reason I wanted to talk to you. You are an extremely careful person, the way that you compose emails, any document you're dealing with. You are a natural proofreader, your grammar is perfect, you don't have typos and misspellings and things you and basically that's the kind of person you want working your White House is my feeling. You want the Kate Shaws of the world who are ... No really, you want people who are just super careful people. You do not want the Chris Hayes' of the world, running your White House operation 'cause I tweet typos all the time and like ... But the White House, they put out official documents all the time, forget legal stuff, that to me is just so indicative of exactly what you're saying.
CHRIS HAYES: The same White House that would just put out a misspelling of a dignitary's name on an official document, is also going to put out these legal documents and that's where the rubber hits the road on that stuff.
KATE SHAW: Every White House and certainly this was true of the Obama White House is doing a million things all the time and is pretty chaotic and everyone is really overwhelmed. So I just think you have to have ... Yes, you have to have people who are by disposition kind of sticklers and careful and I don't get the sense that's the case in this White House. But you also just have to have internal protocols and policies and workflow and org charts and it feels like with the amount of staff turnover they've had, I don't even know if there's a staff secretary right now, honestly, right? That's a really important position in the White House too in terms of controlling the flow of paper into the president's hands and then what comes out of the White House.
KATE SHAW: I do actually have a lot of sympathy for the conditions in which a lot of staff level folks are toiling, it's a really difficult place even under the best of circumstances, I think, to work and I think that you see if you don't have really systems in place that things can kind of fall apart really quickly. Every White House kind of stands its own set of processes at the beginning and that's what so crazy, every White House. There's a very small core of career officials who do IT and human resources and that kind of thing but basically everyone turns over right at the change of administrations in the White House. And so there's no institutional memory whatsoever, so basically this kind of empty building gets filled on inauguration day and you have to figure out how to structure the place anew. Every White House does it by itself, it's really nice to have some people who served in previous White Houses and we did have that at the beginning of the Obama administration.
KATE SHAW: But it is pretty wild just kind of how sort of blank slate the beginning of a new administration is, my sense is that I think if you have a rocky start and this administration I think really did have a rocky start, it's almost impossible ever to kind of overcome that deficit. I think that the transition is a big part of this story actually, so I worked, obviously you remember this, I worked on the transition into the Obama White House. So after the election, sort of November, December, January, 2008 into 2009, and transitions are a really weird period because you have this creature, the president-elect, who's not a private citizen anymore but isn't actually the president. And so it occupies this kind of liminal status and does start going to briefings and begins to kind of get ready to govern but doesn't actually have any governing authority yet.
KATE SHAW: And it's kind of the same with the staff, you're sort of in this interesting kind of extended cross fade, where the outgoing administration is sort of winding down and trying to help get you sort of up to speed to the extent you're interested in their input. And then they kind of just hand over the keys and so if you run a really tight transition, which of course, Lu, who you have on your show a lot was executive director of the transition, so I worked for him in the Obama transition, it was just a really, really well run operation and so you had these kind of top to bottom reviews of every agency, so we had teams that would go into every agency and meet with the top officials and try to figure out how policy development happened there.
KATE SHAW: Where sort of the policy change priorities were, how the offices were structured, so these teams would sort of gather information, make recommendations to the president-elect, and so that when you actually ... When inauguration did happen and everybody did actually report to work as a real government official, you kind of knew what your priorities were and you could actually get down to business like immediately. And that was true in the White House too, sort of try to figure out how all the White House offices were structured and what they did and I'm not the only Obama staffer who would say this, lots of people I think had this experience, the outgoing Bush staffers were lovely, they were so helpful, everybody cares a great deal about the institution of the White House and so people ... Though the policy views obviously the two administrations could not have been more different, it was just like really, really cordial, collaborative meetings about what they did and kind of what do you need to know, what can we do to help was the general attitude. I know that the outgoing Obama staffers, I obviously have been long gone from administration-
CHRIS HAYES: Sure.
KATE SHAW: But the Obama staffers who were winding things down in late 2016, definitely had that attitude I think to the incoming Trump staffers and had binders prepared and were ready and willing to be as helpful as they could be, particularly because this was, obviously this candidate who was himself I think taken aback by the election results, obviously the country was, so they sort of knew this was gonna be a team that was not gonna necessarily come in with a whole lot of government experience. And so my sense was they were really willing to be ... Wanted to be as helpful as they could. And I just don't think that Trump people ever called, like I don't think they really availed themselves of the opportunity to get briefings from and sort of assistance from the outgoing Obama staffers. In part because there wasn't a real transition.
CHRIS HAYES: Right, part of it was that Christie gets named to run the transition and then he gets fired, which is sort of a little bit of narrative foreshadowing from the showrunners of the Trump serial. Because the president is going to keep cycling through staff but from what we know reporting, my understanding from the reporting is that there was a process akin to the one that Chris Lu ran that was like thrown in the trash, essentially. Started up it again-
KATE SHAW: But I'm not sure what really took its place and-
CHRIS HAYES: No, nothing.
KATE SHAW: I don't think those meetings happen in a normal way and they weren't even running the transition from D.C., it was run from New York anyway. I think most Trump staffers didn't report to work for a couple of days after inauguration because it happened on a Friday-
CHRIS HAYES: They took the weekend!
KATE SHAW: And people didn't start going to work until Monday. It just like, I remember, it was unthinkable that you would just sit on two days of actually sort of getting down to business, and anyway ... Ultimately, I don't think that they have ever really recovered from that start.
CHRIS HAYES: I haven't thought of it in those terms, I haven't seen anyone talk about it in those terms of just like, it's a thing you can't recover from in some deep sense that starting the way they started and the chaos. I mean obviously, I don't think they've helped themselves because but even trying to stand up processes after the fact, which sort of brings us to the distinction between the travel ban and DACA. Because on the other side of that, is that the travel ban, okay, they come in, like Stephen Miller maybe drafts it. So it's like terribly drafted, the courts hate it, three different iterations are now defending the third version. DACA isn't like that, the DACA rescission, the taking back essentially DACA, I don't know, comes a year, I think I want to say, right? In the fall they did it, in September around then-
KATE SHAW: Mm-hmm (affirmative).
CHRIS HAYES: So it's comes whatever, nine months in. And yet the courts have been similarly unimpressed with that.
KATE SHAW: So that one was kind of weird in a different way. So you had the Attorney General and the DHS Secretary, basically announce that they were gonna rescind DACA. But the main problem there is the justification just didn't fly. So the explanation that the Attorney General gave was that, DACA was unconstitutional, so that's why they were undoing it. But no court had found that, that's not to say that only courts can decide, the executive branch can decide for itself right? [crosstalk 00:20:14] Things at least, obviously in our system, the judiciary is the ultimate arbiter of constitutionality but the executive branch should make its own determinations of it thinks the constitution means and requires. I don't think that, that's problematic at all, that they say we think this thing is unconstitutional but they sort of pointed to courts as having said that and that actually wasn't true. And the other thing that weird-
CHRIS HAYES: Wait, just stop for a second, to me this is also classic. They said the courts had said it?
KATE SHAW: In Sessions' speech, he basically said, that the courts had found that DAPA, which is this extension of DACA, was unconstitutional but and that the Supreme Court had essentially agreed. I just don't think that's right. So the Fifth Circuit had struck down DAPA, but not on unconstitutional grounds, it found that it was procedurally flawed, it should have been down differently and never reached the constitution question at all, so there was this kind of misrepresentation of what the Fifth Circuit had done. So that's kind of problem one and problem two is that in the announcement that they were gonna rescind DACA largely based on this kind of constitutional flaw that they sort of pointed to the courts as having seen, they said but we're not going to do it just yet, we'll sort of wait ... We'll give sort of this six month kind of phase out period, we'll continue doing DACA renewals during that six month period, and the courts had a hard time with that too. They said, the thing is unconstitutional, why are you going to keep it in place for another six months? It's different from the travel ban-
CHRIS HAYES: It seems like there is something related between the two in that like, again, it's like a failure of process and care. There's a way that you do all this stuff, it's a lawyerly way you do it. You want to do something from the executive, you run a process and you come up ... You explain, we're doing this for this reason and this is why it's defensible, it's basically the work of lawyering that just is somehow not getting done very well.
KATE SHAW: I mean, I think that then the Department of Justice has defended in briefs using this kind of more nuanced ... Well, there's litigation risk and that's why. So it's not that there hasn't been care sort of at any point in the process but the announcement and the roll out, I think you're right did reflect this kind of lack of care and there just are legal doctrines that constrain what agencies are able to do ... Most of the time when the president acts, the president acts through agencies, and agencies can't just change policy overnight without giving some explanation and courts will look at those explanations-
CHRIS HAYES: He’s not a king. This to me is the key thing. The guy's run a private business for his whole life, if Donald Trump, Donald J. Trump, who is the head of Trump Org, a family run business, wants something done, he just says like, "Go do this thing." He doesn't have shareholders, he doesn't have a board, it's a family business, it's like if you run a bodega and you're like, "We're gonna stock the Diet Coke over here." You don't ask anyone to do that, it's your business, you go do it. And I just feel like that leadership style and that posture, there's a fundamental tension ... This isn't even dealing with the other rule of law questions. But even in this banal way, it just seems like there's fundamental cultural tension between the way you do things in that environment, and being the President of United States, when you have to take care the laws are faithfully executed. And be surrounded by lawyers and dot i's and cross t's.
KATE SHAW: And I do think that sort of leadership style issue is connected to these kind of rule of law and sort of legal norms question and my old boss, Bob Bauer, has made this point. That maybe it is the case that when you come up in this private sector background in particular sort of this New York kind of real estate background. You view yourself as constrained, maybe, only by the kind of outer bounds of what you can get away with.
CHRIS HAYES: 100%
KATE SHAW: And sort of in private disputes, that's not necessarily so wrong in that you're aggressive, you get sued, you settle. You sort of see how aggressive you can be-
CHRIS HAYES: Absolutely.
KATE SHAW: And what the cost of settlement will be, kind of this sort of independent weight and value of the law, just isn't something that you really internalized. So I think that, that's ... You do sort of see that attitude toward law I think continuing in this White House.
CHRIS HAYES: Yes, the idea that you push until you can get away with-
KATE SHAW: It's just not the ethos in government-
CHRIS HAYES: No.
KATE SHAW: It never really has been. At least in the post-Watergate era and maybe before that it was. But certainly in the modern era that's not the ethos in government, you push as hard as you can and you see what you can get away with. I do think that is what we seem to be seeing in a lot of spheres.
CHRIS HAYES: Well, that's like there's this sort of leadership style, there's a kind of cultural style emanating from the top, there's a kind of chaos of the beginnings that have sort of emanated through. I do feel also there's this, I don't know, I mean I guess I want to make an argument on character, which is maybe not unfair. Here's an example of how I think about it. The Hatch Act, the Hatch Act is you're not allowed to sort of campaign politic on government time-
KATE SHAW: Exactly.
CHRIS HAYES: But it's sort of complicated because like the president's politicking all the time, what does that really mean? And my understanding is you and your colleagues in the White House counsel's office, in the Obama administration thought about it a fair amount, about what was okay and what was not.
KATE SHAW: A lot of it falls to the White House counsel's office to give briefings to White House staff members on things like the Hatch Act and ethnics and record retention. That's a big deal, there's a Presidential Records Act. So there are very strict rules governing what kinds of materials you can just sort of get rid of the only copy of. You mostly have to save any of your substantive writings under the Presidential Records Act if you're a White House staffer because those are viewed as property of the United States. You can't write a memo, send it around to your colleagues, take the only copy home or shove in a burn bag and dispose of it. You have to retain those under this statute, the Presidential Records Act. There are a lot of examples of these kinds of rules and norms, that you don't show up day one at the White House knowing.
KATE SHAW: So somebody has to instruct you and train you in them and it's usually the lawyers in the White House counsel's office. And in our administration, those happen through a series of briefings that every office would have, and they would have them regularly because I think everyone understood that you ... These White House's are perpetually busy and overwhelmed and over worked places so you can't just send a memo to everyone in their email and say, "Okay now you've been informed how you have to deal with paper work." You actually have to sit down and have face to face conversations with everyone to kind of instruct them in all of this. I don't know if any of that has happened.
CHRIS HAYES: It's funny because as I listen to you it's like my instinct is to be like, these are people who don't care. They just don't care like as character judgment about this stuff and it's interesting to hear you say, well I don't know about their character, there's a process issue here. Which is like no one is briefed them or given them the tools to know to care.
KATE SHAW: I don't know that, this is totally speculation but I know enough about the dynamics of those early weeks and even first couple of months, to suspect that it didn't happen in kind of as rigorous and regimented a way as it did in the early days of our administration.
CHRIS HAYES: There's also this sort of deeper question which sort of relates back to this idea of him as real estate mogul and what you can get away with, which is like, who cares about the Hatch Act and Presidential Records Act. Who is gonna enforce it? Let the Pope send his army kind of thing. At one point Kellyanne Conway, this was the iconic example, Kellyanne Conway goes and says like, people should buy Ivanka Trump's clothing and she gets some ethics office recommendation against her that she shouldn't have done that and there's been a few moments where it seems like the may be in violation of the Hatch Act. I think there's one actual finding. It's like, right and that and $2.75 gets you on the subway. It doesn't matter and part of what I think the feeling of legal crisis that we're in is just like, if you take the approach of push and push and push and see how far you can push. What you find is that a lot of it just pushes over.
CHRIS HAYES: If you're like, yeah, just push the Hatch Act, who's going to stop us and the answer is no one's gonna stop you. It's not always the case, when you're talking about the Muslim ban, you're talking about DACA, the courts have sort of retained their authority. But in all these other ways, these kinds of lawyerly norms and lawyerly institutions about all these stuff. For instance, don't tweet threatening the Justice Department to stop investigating you and your campaign. Yeah, who's going to stop you.
KATE SHAW: I mean, I totally agree with that in some ways, one of the things that have been so striking about this era is the way that it has exposed the degree to which a lot of government conduct is governed more by norms than hard law and so there are norms regarding the dependence of the Justice Department and there are policy memos that White House counsel's have issued going back a number of administrations that really narrow the universe of conversations that can happen between political staff members and the White House. And this law enforcement agency that has this kind of awesome prosecutorial power particularly when it comes to criminal matters. But just that context between those two entities should be really limited and carefully monitored. That's a long standing tradition but there's no law that says that the president can't pick up the phone and call the Justice Department. It's mostly norm governed, not law governed.
CHRIS HAYES: To me, his tweets about the Justice Department and his comments about the Justice Department are remarkable. I mean, he is in front of everyone, threatening the Justice Department to stop investigating a criminal investigation of his campaign, his family members and his associates. It's just rank intimidation, it's one of those things when you get to the DACA decision, you get to the travel ban, where you feel like you've come up against a hard stop. There's nothing to say, don't do that. I mean, I can whine about it on my show, say, "This is ridiculous." But that is part of a broader, in some ways maybe the most kind of iconic way in which this presidency and its relationship with the law and the norms is different is the speech of the president. The way that he talks, what he says, what he's willing to say, what he says on Twitter, which are things that are just not conceivable prior to him and have had ... You wrote a great law review article entirely, largely about this, about how the president's speech, not just this president but generally the president's speech sort of should be considered legally has played a huge role in both this presidency and in some ways the legal problems he's faced.
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KATE SHAW: So the travel ban litigation is the kind of prime example of this but I think in a number of cases, his Twitter account and his speech in general are just kind of a huge problem for the lawyers trying to defend the policies of his administration. And I think as long as he continues to tweet in the style that he does, that's gonna continue to be the case. And so in DACA, in travel ban, in this sanctuary cities litigation, court after court has sort of looked to presidential speech as either, undermining positions of the Justice Department, supporting claims made by challengers.
KATE SHAW: And I actually have this sort of idiosyncratic view that I offer in this article, which is that I actually think some of the time, courts should set aside what the president says. The president should, whether it's this president or President Obama, or any other president, should be able to speak freely on a wide range of topics, without necessarily binding himself or his administration to litigation positions and I continue to think that.
CHRIS HAYES: Yeah, you can't do the job if everything you say all the times defacto becomes some irreversible considered legal opinion of the executive.
KATE SHAW: Yeah, I mean not everybody agrees with this but that's my general feeling-
CHRIS HAYES: I'm persuaded by your view by the way.
KATE SHAW: Thank you. But in the travel ban case and in a lot of cases where there are arguments that the president is expressing animus, bias, that in those kinds of circumstances it's totally appropriate for courts to take seriously what the president says. I think that there is a distinction that you can draw but he's been I think, he seems like a difficult client I think for lawyers, the lawyers around him. And the litigators trying to defend this stuff, I think have a very difficult time and you see the tweets of his end up getting, entering filings-
CHRIS HAYES: Cited.
KATE SHAW: Within hours sometimes because he does, he continues to tweet about high stakes, ongoing legal matters. They both involve his administration's policies and also potentially his personal, legal exposure, but no one's been able to talk him out of it as far as I can tell, right? There's this lawsuit ... So he blocks people on Twitter, so this-
CHRIS HAYES: Funniest, pettyist thing in the universe.
KATE SHAW: That he keeps blocking people?
CHRIS HAYES: Yeah, I mean, first of all just it's a hilarious thing to imagine, him sitting there scrolling through the phone and being like, blocked, blocked, blocked. I don't like your trolling comment to me the powerful person in the planet, B, you can mute people, and C, this is a thing that there's a lawsuit over. That the United States government is defending the president's ability to block people.
KATE SHAW: Yeah, so I kind of can't believe D.O.J. lawyers are briefing this. The president has the authority to block people on Twitter, that's the position that they're taking and the lawsuit, if somebody could just convince him to stop blocking people, right, just mute them.
CHRIS HAYES: Literally, a judge offered that.
KATE SHAW: The district court sort of suggested this in the hearing on the case a couple of months ago-
CHRIS HAYES: Have you heard of muting, Mr. President?
KATE SHAW: But he doesn't seem to be willing to do that. And that's a case in which I worked for obviously President Obama, and I still have a pretty robust view of presidential power and I don't like the idea of making unnecessary law that might constrain the ability of the president in ways I might actually really care about, when you can make the whole thing go away if he could just be persuaded to stop blocking people. But it feels like somehow emblematic of larger themes.
CHRIS HAYES: But I think this is what to me part of what it comes down to, as I try to think about this, I really do view ... A lot of my experience of watching this administration is in some ways just because ... In those years of you working in the Obama administration, I just got to see a certain part up close, I saw how hard the job is, how demanding it is, the stakes of it which are insane. Not to get too real world here, but you're like, "Well, my spouse isn't spending enough time with me." No, it's literally the most important job in world. You can't win that argument. That job is the most, it's such an important job, it's a hard job.
CHRIS HAYES: I think there's something about both Barack Obama, Harvard Law, editor in chief of Law Review there, professor, lawyer, the people that work in the White House like yourself, I feel like people in that White House knew they couldn't get away with things. He was Barack Obama, he was the first black man in the White House and I just feel like part of the care came from within your souls and who you were as people and part of the care came from a very good lawyerly culture and part of the care was like, we have zero room for error.
KATE SHAW: First, I should say I'm sorry if I ignored you for two years.
CHRIS HAYES: You made the country a better place, you didn't ignore me, you did not ignore me.You worked hard, you worked really hard.
KATE SHAW: I was gone a lot.
CHRIS HAYES: I played a lot of pickup basketball.
KATE SHAW: Yeah, you were a little lonely sometimes.
CHRIS HAYES: Look, it's really useful to talk to you because it grounds me back in the sort of lived reality of that place, which you have I think, a lot of personal kind of empathy connection to, that it's easy to lose sight of when you're watching it. Yeah, it's a hard job and it can be a lonely job on both sides, obviously.
KATE SHAW: Yeah, you can't talk about a lot of what you're working on with your spouse, particularly if you're doing a lot work with classified material. I think it's right that we knew, we thought we couldn't get away with anything, but I don't think we wanted to get away with anything. I mean you're there in just this unbelievable position of public trust and you ... The idea of using it for any kind of self-dealing purpose, I don't think would ever have, I don't know, I don't think would have entered the minds of most staff members who were there, if any. To the extent you're sort of wrestling with hard questions, it's like, if there's any tension between your obligation to the president as the president and the institutional kind of office of the presidency and the American people. You sort of are thinking about all of those possible clients and you're a White House lawyer.
KATE SHAW: I'm not suggesting that particular staff members in this White House are doing that at all either but I don't think that getting away with anything was something that we avoided doing because we thought that we'd get caught.
CHRIS HAYES: I don't think that, what I think is that there was a standard that everyone was held to that you were constantly thinking of, which is that you were always walking through a minefield. I felt like that was very present in everyone's mind. I don't know maybe that I don't have a comparison set, it's just you, the only person that worked in the White House that I lived with but I don't know if that particular to Barack Obama and the Barack Obama White House. It did feel to me that that was kind of the case, that like there is no room for error with this man and this moment.
KATE SHAW: Yeah, I mean it's the only White House I ever worked in so it's hard for me to compare either but I do think that we ... The expectations were really, really high. I was not in a lot of meetings with the president but I remember going in to one where we had another associate White House counsel and I had to put together a memo in some unbelievably short period of time, 36 hours and we had read so much and not slept and written this memo. It was like 10 or 15 pages, we sort of walked in and he knew how quickly we had ... I think he knew when the ask had gone out and he knew that it was two days later that we were in there briefing him, and I remember thinking like, I wonder if we'll get some kind of atta boy, you guys really turned this around quickly. And there was none of that. Because the expectation was like, this is White House, we're in the oval office, I need a memo and I need an excellent memo and I need you to turn it around as quickly as I need it and no one's really gonna get a cookie for doing that.
KATE SHAW: Being here is kind of is sort of the reward in of itself. So there were just incredibly high expectations, I think that those emanated from him. He obviously performed at unbelievably high levels, read incredible amounts of briefing materials and just always demonstrated mastery that surpassed every subject matter expert in the room. You went to a couple of round tables with him-
CHRIS HAYES: Right.
KATE SHAW: And you always had the same feeling, he was so smart, he was thoughtful, he was so well prepared and so you kind of had to reflect that back to him to the best of your ability.
CHRIS HAYES: And I want to, just to be clear, all of these determinations of Barack Obama, there are lots of things that I personally think that he did wrong-
KATE SHAW: Sure.
CHRIS HAYES: His administration and really significant failures I think in that administrations on a substantive level. I just think that the baseline of integrity it's just not even ... Whatever those mistakes were, they were mistakes that were made on sort substantive grounds and not because he wanted more members at his golf course. Which is what is happening now. Which again it's like you can't even, you just sort of can't, you can't conceive it.
CHRIS HAYES: This might be putting you on the spot so you don't have to answer it but I don't think we've ever had this conversation, what would you say, I know you know some people because of the very sort of small world of elite law that you had moved in, former Supreme Court clerks who particularly tend to be the kinds of people who end up in these sorts of administration jobs. That you know people who I think worked in this administration, I think one or two of the people you clerked with in your clerking class, what would you say to someone who was about to take a job in this White House, as a lawyer?
KATE SHAW: I think that answer's probably changed since the beginning of this administration. I think early on I was persuaded that everyone should go in and there's nobility in government service and you can be sort of a righteous lawyer in any set of circumstances. Even if you don't align perfectly with the views of Donald Trump, go serve it's an incredible honor, you can do great good from the inside. And you used the term, I think you used it on your show, you certainly use it off air, this dignity wraith term which is not yours-
CHRIS HAYES: It's a Josh Marshall term.
KATE SHAW: Oh, it's a Marshall term.
CHRIS HAYES: I wish it was mine but no, it's not-
KATE SHAW: It's a really good ... But just that association with this administration has not been great for the reputation of a lot of people, a lot of lawyers, and so I think it doesn't feel like you can necessarily do that much good on the inside. Now that's talking about political positions, I still have friends and former colleagues who are in career positions in the Justice Department and elsewhere in the administration. I think that it's good that they're still inside and-
CHRIS HAYES: Deep state. That's the deep state.
KATE SHAW: No, they're career lawyers who have been there from administration to-
CHRIS HAYES: They're trying to bring down our president, it's fine, it's cool.
KATE SHAW: Administration.
CHRIS HAYES: You know the people that are trying to bring down our president from the inside who are part of the deep state, that's what you're saying.
KATE SHAW: This is not the headline I want coming out. But I think it's good that they're there. I think that political positions are maybe a different story at this point.
CHRIS HAYES: I was gonna pause and do an outro of your bio. Kate Shaw is a professor of law at Cardozo-
KATE SHAW: You do have to say Cardozo at some point.
CHRIS HAYES: Yeah, Kate Shaw is a professor at a law school here in New York, it's name is, no. Kate Shaw is a professor of law at Cardozo University. She was a former associate White House counsel in the Obama administration, she's a legal and Supreme Court analyst for ABC News, the mother of my three children, love of my life, also. Most importantly her birthday and the greatest lawyer of her generation.
KATE SHAW: Stop it. Cut all of that please!
CHRIS HAYES: I hope that's being heard right now in the ears of all the people out there because it's absolutely true, all right, I love you.
KATE SHAW: I love you too.
CHRIS HAYES: "Why Is This Happening?" is presented by MSNBC and NBC News Think, produced by the "All In" team with music by Eddie Cooper.