Richard Nixon, Donald Trump, Watergate, Stop the Steal
Richard Nixon (top left), Donald Trump (top right), Watergate complex in Washington, DC (bottom left), and Stop the Steal rally at the US Capitol (bottom right). Photo credit: © Consolidated Arnie Sachs/DPA via ZUMA Press, ep_jhu / Flickr (CC BY-NC 2.0) , Trump White House Archived / Flickr, and Tyler Merbler / Flickr (CC BY 2.0).

Author and filmmaker Shane O’Sullivan on the still-hidden mysteries of Watergate.

Next Friday marks the 50th anniversary of the Watergate break-in, an event that brought down a president and taught us to be unremittingly cynical about politics.  

In this week’s WhoWhatWhy podcast, we talk with political historian and filmmaker Shane O’Sullivan, whose latest book is Watergate Burglars: Nixon, Dirty Tricks, and the CIA. 

Among the topics discussed: What, if anything, can the history of Watergate tell us about the January 6, 2021, insurrection/riot at the US Capitol — the subject this week of long-awaited hearings by a House subcommittee? 

O’Sullivan points out that Watergate was investigated by a bipartisan Senate committee, which held hearings on live television, and that many books and films have been produced about the presidential cover-up. Yet, we still know little about the Watergate burglary itself, why it was so bungled, and what its real objective was.

He raises the question of whether the burglary was sabotaged, and discusses the multiple motives of those who planned and executed it, and the Rashomon-like aspects of the deed that have never been resolved.

One thing O’Sullivan stresses is the difference between the personalities and governing styles of Richard Nixon and Donald Trump. He reminds us how much of what Nixon did was hidden behind his dissembling façade, whereas Trump famously spoke the “quiet parts out loud.”

The fact that our Republic survived Nixon and Watergate may be the only optimistic lesson to be drawn from this sordid history. More troublingly, it’s hard to imagine we’ll ever know the truth about January 6 — when we still don’t know the whole truth about Watergate, 50 years later. 

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Full Text Transcript:

(As a service to our readers, we provide transcripts with our podcasts. We try to ensure that these transcripts do not include errors. However, due to a constraint of resources, we are not always able to proofread them as closely as we would like and hope that you will excuse any errors that slipped through.)

Jeff Schechtman: Welcome to the WhoWhatWhy podcast. I’m your host, Jeff Schechtman. June 17th marks the 50th anniversary of the Watergate break-in. For many, the events of the Trump years have given new perspective to those Watergate events. It’s caused many to call this new era worse than Watergate. We’ve talked to you before about how the events of the present may not really be understood for another 50 years. Given that benchmark, perhaps this is the ideal time to go back and look at Watergate.

While we know so much about the chronology of reported events, there is still so much that we do not know about the individuals, many of whom have since passed, who participated in many aspects, some unreported, of the full Watergate story. We’re going to talk about that today with my guest Shane O’Sullivan. He’s an author and filmmaker. His work includes the acclaimed documentaries RFK Must Die, Children of the Revolution, and Killing Oswald, as well as the book Who Killed Bobby?

His newest book is Watergate Burglars, Nixon Dirty Tricks, and the CIA. He also led a recent seminar to mark this 50th anniversary of Watergate. And it is my pleasure to welcome Shane O’Sullivan back to the WhoWhatWhy podcast. Shane, thanks so much for joining us.

Shane O’Sullivan: Great to be here, Jeff. Thank you.

Jeff: It’s good to have you here. First of all, how do you think that our view of Watergate and the malfeasance of Watergate has somehow shifted as a result of what we’ve experienced over the past four, five years?

Shane: I think so many parallels have been drawn [to] the Mueller investigation, the impeachment hearings of the Trump presidency. I’ve actually written, I think, seven pieces for The Washington Post drawing some of those out. The echoes are there, and the echoes show that we haven’t learned that much from Watergate. We’re bound to repeat some of the history of Watergate and what’s going on.

I think the difference, for me, is, obviously, Nixon had a public face and the private face. The public face still had the aura of the presidency and the sanctity of the White House and the idea that these idealistic men were working on behalf of the country. And then when we heard the Nixon tapes, and we heard the cynicism and the cover-ups and so on, that veil fell. And I think that creeping cynicism around politics then ate away a belief in the system and faith in the major political parties.

Whereas you could argue, with the Trump presidency, I suppose, the public and the private face are the same, given the results of Twitter and then basically the off-the-cuff remarks that we were used to.

Jeff: Does the cynicism that grew out of Watergate, the cynicism about politics, politicians, the political process, does that still shape our view today, or have we gone past that by a couple of generations, do you think? Or is it still in our political DNA?

Shane: I think it’s still there in the political DNA. Even at the conference, The Watergate Break-In 50 Years Later, it’s interesting some of the response of that in social media because it folds very much into party lines. The Democrats are bringing this up as a political tool. And they themselves did the same or worse to the Republicans at various points in history since Watergate. So I think the actual era now is so polarized to both sides of the political arena.

Whereas back at the Watergate time, certainly, at the time of the Senate Watergate Committee, there was truly a bipartisan feeling to the hearings, where they were working together to find out what had been done within the White House and to ferret out the truth and let the chips fall where they may.

And [Republican] Senator Howard Baker was one of the key movers behind that, a man who had been very close to Nixon, but then ultimately realized that Nixon and the men around him had been covering up almost from the first day after the burglary.

Jeff: And yet, even with the bipartisanship and the sense of everybody working together to uncover what had happened, there is still the sense to this day that we don’t know everything. That there was so much still hidden.

Shane: That’s right. I think there’s so many mysteries that remain about the burglary specifically because [things were] overlooked. I guess the movie All the President’s Men and the book of the same name, through the focus really on Nixon and those around him who were involved in the cover-up, and everybody forgot about the burglars and some of their associations to the CIA and why they went in there in the first place.

And if you talk with the lead Watergate prosecutor, Earl Silbert, or the FBI case agent, Angelo Lano, they will tell you that they still don’t quite know why the burglars went in there or what they were looking for. And there was also an element of bungling and lack of clarity on behalf of the burglars themselves in terms of when they first went in during the first break-in, they didn’t actually know where the office was of Larry O’Brien, the DNC chairman, who was their primary target.

It seems unbelievable, too, but that was the case. That was why they planted a bug on the wrong phone, and they had to go in a second time on June 17th. And, having planted the bugs in the early break-in and tried to move them to the right phone the second time they went in, that was ultimately how they were caught and how Watergate became the huge scandal that it was.

Jeff: How was the incompetence explained? You’ve looked at all of this. You’ve heard so many of the theories. The complete incompetence, almost the gang-that-couldn’t-shoot-straight ability or lack of ability of this group.

Shane: It is baffling. On the one hand, here are highly trained professionals, many of whom had years of service with the CIA in official capacities as CIA officers. James McCord was head of physical security at the CIA for many years and then became the security chief for the Nixon campaign at the Committee to Reelect the President. E. Howard Hunt, again, a very seasoned professional.

So you’d wonder how they made some of these elementary mistakes, especially because they’d actually successfully been in the first time over the Memorial Day weekend. They’d planted the bug thing, masking tape to keep the doors open on the stairwell up into DNC headquarters. So they’d done it once, and they’d done it successfully. And you’d wonder why so many mistakes crept in the second time.

The key mistakes being that James McCord followed the rest of the burglars into that stairwell and up the stairs to the sixth-floor offices of the DNC, but he didn’t remove the masking tape that had been left on the door to make sure the door didn’t lock, and they wouldn’t be able to get an entry. So, of course, Frank Wills, a security guard, ultimately found that masking tape the second time after noticing it about half an hour earlier. And that’s when he raised the alarm.

Also, McCord, over the walkie-talkies, he could hear interference on Bernard Barker’s walkie-talkie and advised them to turn it off. And then because Barker, being in DNC headquarters without a walkie-talkie to alert him, that was another reason why they couldn’t take counteraction and get out of there before they were rumbled. So it is baffling.

You can either see it as a third-rate burglary with bungling on behalf of the key operators, or you can potentially see an element of sabotage on behalf of one of the senior burglars. If you ask FBI Case Agent Angelo Lano, he actually thinks there was an element of sabotage from within the team, that one of the burgers led them into a trap, that they wanted this bugging activity to end in DNC headquarters, and he suspected the leader, Hunt or McCord, knew in advance what was to happen.

And some of these mistakes may have been intentional.

Jeff: And what would have been some of the potential reasons for that?

Shane: My own theory — again, it’s very speculative — but I mentioned it in the new afterword to my book. I think McCord is the most elusive of all the burglars in terms of his motivations.

He came out with a fascinating PowerPoint to his family shortly before he died, which basically says that as well as being asked to go in there to plant the taps on O’Brien’s phone and for the orders to photograph documents, he actually thought that Vietnam Veterans Against the War — an anti-war organization, a very militant anti-war organization at the time — had a mole inside the DNC that he thought he could get more information by bugging some of these phones and secretly photographing some documents that might reveal who the mole was.

But also, his whole, I guess, perspective was very far right at the time. He was very skeptical of Nixon as not being a true American, obviously, receiving public acclaim for his moves towards the Soviet Union and with Red China, which McCord was very distrustful of.

And if you look at those around McCord in the weeks and days before and after his arrest, they were a number of figures who were associated with an organization called the American Security Council, which is a far-right organization full of former Chiefs of Staff of the Joint Chiefs of Staff, ex-military figures, who were leading the voices of doubt about Nixon’s moves towards [détente] with some of America’s Communist enemies.

So if there was a hidden ploy to unseat Nixon and stop these moves towards [détente] with a scandal like Watergate, that’s one possible speculation as to McCord’s secret motive, which never actually surfaced before his death.

Jeff: Is it possible that there were multiple motives of different individuals with respect to bugging the DNC — that McCord may have had his, that the committee to reelect may have had others, that there were different people with different motivations — and that’s why it’s been so hard to try and identify a single one?

Shane: I think so, yes. I think there was even Jeb Magruder and John Mitchell, who’s allegedly the person who ordered the break-in or gave his consent to the money being used for these purposes.

I guess their professed motive was to bug O’Brien’s phone because they saw Larry O’Brien, DNC Chairman, had been their most talented and most potentially dangerous political enemy in terms of unveiling some of the dirty tricks the Republican Party had been up to, like the ITT scandal in early 1972. They feared what kind of opposition research Larry O’Brien had in his top drawer on them.

So they broke into his office, and they, hopefully, bugged his phones to try and just decipher what dangerous material he may have had to use against them on the presidential campaign. McCord, we’ve talked about his hidden agenda.

There’s also an element where the Miami buglers, the Cubans, were lured into participating in Watergate with the promise that if they were the fall guys for the operation, if they did this national security operation on behalf of Hunt, that then, if Nixon got into office again, there would be another invasion of Cuba, and then there’s an attempt to liberate their Homeland. So that was the story they were sold to get them involved.

So it’s a very interesting rational story where everybody has their own motives, and nobody’s quite sure of the big picture.

Jeff: And then there’s the fact that this wasn’t the first break-in — not just the first break-in that happened on May 28th, but the dirty tricks and break-ins had been something that had been going on for a while.

Shane: Yes, I think this is something that the Nixon campaign said at the time: that this is part and parcel of any American election season, but nobody ever got caught before. And there are even echoes to the Anna Chennault shenanigans during the 1968 election which never quite came out at the time, but ultimately, in the early ’80s, they surfaced.

I think the difference here is, here was a former attorney general of the United States, who is now in charge of the Nixon election campaign, giving his assent to this plotting. And then, obviously, the fatal mistake was, allegedly, because their budget was cut, they had to turn to McCord to be part of the burglary team, and obviously, once he was caught and identified, he was identified as the security chief for the Nixon campaign and being arrested inside Democratic National Committee headquarters.

So it was a dead giveaway tying the Nixon campaign to this burglary. For a time in the initial prosecution, sealing that off so that the White House wasn’t directly connected, but ultimately, after the burglar trial and McCord’s famous letter to Judge Sirica, gradually, it crept towards the doors of the White House and then implicated several important figures around Nixon, and he himself was named as an unindicted co-conspirator.

Jeff: Talk about the additional whistleblower that emerged later on.

Shane: I think one of the key ones who died recently was Alfred Baldwin, and his is a fascinating story.

He was recruited by McCord, and he was the one who was both the lookout in the Howard Johnson motel across the street, looking down from a seventh-floor room directly into DNC headquarters on the night of the June 17 break-in; and also, for three weeks up to that point, listening to the conversations on Spencer Oliver’s phone to dig for any political or perhaps sexual intelligence material on Democratic officials that, again, could be used against the Democratic campaign.

So he is a fascinating figure because he alone heard up to 200 conversations on those phones, but then because of a statute not allowing him to share any of that privileged information, because of the wiretapping statutes, it essentially remained in his head. Only he knew the true story of what was said in those conversations. And he took the secrets of those to his grave, aside from some of his grand jury testimony unveiling some of it.

So he was a fascinating figure. And the whole hidden motive of McCord and his ties to far right-wing groups was very much a theory that Baldwin subscribed to before his death.

Jeff: What are some of the largest mysteries that are still surrounding Watergate?

Shane: I think, really, the key question is why they made so many elementary mistakes and if McCord, such a seasoned professional, truly made these mistakes because of the pressure he was under or because of miscommunication with the rest of the team, or whether there was an element of intentionality to it, and that there was some plan to the break-in that hasn’t surfaced so far.

I think what I find mystifying in the general debate around the break-in is the prominence of the Woodward and Bernstein element of it and All the President’s Men thing, but that’s only a small part of the story. I think the buglers themselves and their motivations are just as interesting and give us a lot more light on what actually happened.

Jeff: Where do other elements of the CIA fit into this, and what did they know about this?

Shane: Jeff Morley has a new book out, which I think is out tomorrow, so obviously I haven’t read it yet. And he’s looking at the history of the relationship between Richard Nixon and [CIA Director] Richard Helms, and certainly, it wasn’t a friendly relationship. And it went back to the JFK era, and a lot has been said about the links between the secrets of the Bay of Pigs and the JFK assassination and how Nixon may have put some leverage on Helms to get to the bottom of that in the wake of Watergate.

It’s certainly true that the Nixon campaign tried to use the connections of the burglars to the CIA as a decoy to throw suspicion away from the White House and cultivate the sense that it was a CIA operation. But I would say, after the first week, when the FBI suspected that might be the case, gradually, they understood that actually, despite these connections, it was unlikely that the CIA was directing the operation, certainly from Langley or from Richard Helm’s perspective.

And that actually the Nixon campaign was just using that to deflect attention from themselves. My own belief, having really written my book with that potential premise in mind, I don’t think Richard Helms had advance knowledge of the break-in. I think he did cover up a lot in the wake of the break-in to protect the agency’s name and didn’t want the agency to be sucked into it.

And I think if there was any involvement of other CIA figures, I think they’re likely to be retired CIA figures or elements of retired military who would’ve been in league with McCord, but I don’t think he would’ve been working directly with the agency on this operation. At least, I’ve seen no evidence to that effect.

Jeff: Talk about Liddy, and how he fits into this picture.

Shane: Liddy was a fascinating character. I think he was the leader of the operation, the mastermind, if we can use that word — Liddy and Hunt. He was the one they all looked to as the leader. He was monitoring the operation in the Watergate hotel room, to and fro, while the operation was in process. And then he and Hunt fled and escaped when the other five burglars were arrested. He’s unique in the fact that he never talked. He kept his silence.

He’s, I think, served the longest jail time because he refused to speak, which he saw as a traitorous act in not staying loyal to the president. But ultimately, I think he may not have known everything about the operation. I think if McCord did have a hidden agenda, or there were some other players involved, even he [Liddy] may have not known the true narrative of Watergate.

Jeff: Talk about Dean, because there’s been a lot of talk over the years about his connection — peripheral though it may have been — to the CIA.

Shane: I think Dean is quite interesting in terms of I guess taking a lot of evidence like Howard Hunt’s notebooks or his operational diaries, as Hunt himself called them, and hiding them away and not telling investigators about them until Dean had cut a deal with prosecutors in November 1973; and then finally told them he destroyed them one weekend during the burglars’ trial.

So I think while Dean is held up as this whistleblower who ultimately revealed the truth about Watergate and who had to wait until the discovery of the Nixon White House tapes to corroborate his testimony, I don’t think he’s a squeaky clean figure. Because ultimately, his story really served to serve himself and to get him off the hook and to encourage the prosecutors to do a deal with them, even though he’d actually destroyed evidence very early in the case.

So he’s obviously an interesting figure in terms of his amazing memory recall and how later that testimony was corroborated by the Nixon White House tapes, but I think it’s also self-serving at various points, in terms of what he said at various points and what he forgot to say, let’s say.

Jeff: And coming back to Helms, the belief that many had that some of this was all of an effort to bring Nixon down, that the CIA was somehow involved in.

Shane: I was intrigued by that possibility, but I really saw no evidence for it ultimately in the research for my book. I think what’s quite powerful for me is an address that Helms gave to an assembled CIA gathering at the end of June, which is actually in a film project that I’m working on at the moment. And he stands up there very confident, assuring the assembled CIA throng that the CIA had absolutely nothing to do with the Watergate break-in despite all the brouhaha that was going around the press about it at the time.

And everything that I’ve seen in terms of his reaction to the break-in, I think, sprang from a desire to protect his institution and his instinct to cover everything up rather than to cooperate with investigators, no matter what agency they’re contacting them from. And I guess the beauty of Watergate was that, ultimately, a lot of that documentation came out. And indeed, the internal CIA history of Watergate was published in 2016, which became the beginning research for my book.

And all of that leads me to the belief that he didn’t actually know about the break-in in advance and that he was just reacting and being the Mandarin head of CIA reacting, as you might expect in that situation, where he covered things up, he made sure none of this became public, and he tried to distance the CIA from it in whatever way he could. Ultimately, it came out, and he was prosecuted for lying because of other things.

And it’s fascinating his relationship with Hunt. They had a very close friendship, and Helms, right up until the Watergate break-ins, was actually promoting Howard Hunt’s spy novels to Hollywood Studios for film and television adaptations. And I can’t really imagine him doing that and tying himself so closely to Hunt if he had advance foreknowledge of the break-ins, and he knew that the agency was potentially going to be implicated.

Why would he have this relationship with Hunt and be going to the screenings of The Godfather in May 1972, pitching Hunt’s books, hoping to use Hunt’s spy novels to create an American competitor to James Bond [if] he knew weeks later, the burglars were going to be going into the Watergate Office building and putting the agency in great danger if they were caught?

So, I think, for all of those reasons, I concluded that Helms didn’t know in advance, but the whole paper trail in terms of how the agency responded and the voluminous documentation of that in terms of their internal history, and the various testimony Helms was asked to give is really fascinating.

Jeff: The other thing that’s fascinating from a speculation point of view is what if the burglary had succeeded, if the taps had been set, and the burglary was successful?

Shane: Well, the curious thing is they really never thought they were getting very much information from the taps in the first place. Magruder and the Nixon campaign were very disappointed with the initial take from the telephone taps and from the documents that were photographed. That’s part of the reason they went in again. But also, at this stage, you got to remember that really, they were doing well in the polls. It looked like McGovern would be the Democratic candidate.

He was the candidate that they wanted because he was so far left, an antiwar candidate that they really thought had no hope of winning — eventually, Nixon winning the landslide with McGovern only winning two states. So really, what gave Nixon the landslide was the McGovern nomination. So I think the one bit of political intelligence they potentially got was that Spencer Oliver was the fulcrum, where his office was, where the McGovern campaign was being organized from.

So they hoped to go to the convention and organize an opponent [to] McGovern that would steal away the nomination before McGovern was crowned there. And obviously, the [Nixon campaign] didn’t want that because they felt McGovern would be the easiest contender to go up against. So there was some nuggets of political information they were getting, but not very much. So it is baffling why they went in at all.

But I think it speaks to the general paranoia they were feeling at the time, where they felt the White House was besieged by the anti-war movement. Obviously, McGovern had links to that politically, in terms of where he stood in his campaign; and this also led to the paranoia that there were VVAW operatives working inside the DNC. And I think that fueled them to overstretch and do this very risky operation, when, really, rationally, they’d no need to do it in order to win the election.

Jeff: And, Shane, tell us about this conference that you’ve recently participated in.

Shane: That’s right. So it’s a two-day online conference called The Watergate Break-In: 50 Years Later. The website address is And so if you go to the web link, you can see an amazing program, including Earl Silbert, the lead Watergate prosecutor; FBI Case Agent Angelo Lano; Timothy Naftali, who you may have seen on CNN, former director of the Nixon Library; and many more.

Jeff: And what is your sense, finally, of the degree of interest in Watergate today? You’ve been dealing with this for a while with the book, now with this conference. What do you sense is the degree of interest out there in the public?

Shane: I think it’s waned for a while, but I think it’s come more into view as it becomes more politically relevant, really. So around the time of the Mueller investigation and the Trump impeachment hearings, I think the parallels made it obvious. And I think some of the documentaries and the recent TV series Gaslit, they don’t actually mention any events during the Trump presidency by name, but the resonance is obvious.

So I think that’s what makes it compelling to a younger audience and timely for maybe an audience that lived through it. Obviously, the January 6 committee hearings begin. Here, we have more resonance in terms of what happened 50 years ago and what’s still happening today. And you could argue back at the Watergate hearings, as I said, they were very bipartisan.

And at the end, it was really a critical mass of Republicans on Capitol Hill felt that Nixon had to go, that the evidence was there, and they helped push him out when they needed to — whereas obviously it’s a much more divided political landscape today. So it’s not as cut and dry and it’s far more polarized. So it’s interesting to look at what’s happening today through the lens of Watergate and the lessons they can give us.

Jeff: Shane O’Sullivan, his book is Dirty Tricks: Nixon, Watergate, and the CIA. Shane O’Sullivan, I thank you so much for spending time with us here on The WhoWhatWhy Podcast.

Shane: Brilliant. Thanks very much, Jeff.

Jeff: Thank you. And thank you for listening and joining us here on The WhoWhatWhy podcast. I hope you join us next week for another Radio WhoWhatWhy podcast, I’m Jeff Schechtman. If you like this podcast, please feel free to share and help others find it by rating and reviewing it on iTunes. You can also support this podcast and all the work we do by going to


  • Jeff Schechtman

    Jeff Schechtman’s career spans movies, radio stations and podcasts. After spending twenty-five years in the motion picture industry as a producer and executive, he immersed himself in journalism, radio, and more recently the world of podcasts. To date he has conducted over ten-thousand interviews with authors, journalists, and thought leaders. Since March of 2015, he has conducted over 315 podcasts for

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