On with Kara Swisher - Chris Wallace Explains How JFK (Possibly) Stole the 1960 Election

Episode Date: October 10, 2024

After more than five decades in broadcasting, Chris Wallace has won almost every award in journalism, including three Emmy Awards, the duPont-Columbia Silver Baton, and the Peabody Award. The host of CNN’s Who’s Talking to Chris Wallace and The Chris Wallace Show (tune in on Saturday mornings to see Kara spar with Chris and the other panelists) is also an author.  His latest book, Countdown 1960, narrates the twists and turns of the 1960 presidential contest between John F. Kennedy and Richard Nixon. Wallace makes the case that JFK and the Democratic machines in Illinois and Texas committed massive fraud to steal the election from the Republican candidate — and that Nixon did the right thing by conceding. Chris lays out the evidence behind his claim, and then, as we head into the 2024 presidential contest with an election denier, he and Kara break down the lessons and implications for democracy. Questions? Comments? Email us at [e-mail] or find Kara on Threads as @karaswisher Learn more about your ad choices. Visit podcastchoices.com/adchoices

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and the Peabody Award. He's the host of CNN's Who's Talking to Chris Wallace and the Chris Wallace Show, where yours truly is a panelist. He's also the author of Countdown 1960, which narrates the history of the 1960 presidential election between John F. Kennedy and Richard Nixon, and that's going to be the focus of our conversation today. 1960 was a hard-fought and extremely close election that famously included the very first televised debate. But even more interestingly, it might have been stolen through massive fraud in Texas and Illinois. Wallace chose to write about 1960 because it provides such a sharp contrast to 2020 when former President

Donald J. Trump claimed the election was stolen from him and refused to concede. The election was not stolen from him, as was proved numerous times in many courts across the country. We're going to dive into the nitty-gritty details of the 1960 election, including the fraud that might have tipped it to JFK's favor, and explore why and when a candidate should concede defeat, even if they've been cheated. And we'll look to the near future and break down what could happen to our democracy today if a losing candidate refuses to concede again. Our expert question today comes from a CNN colleague of Chris Wallace's, Jake Tapper. Now, let's get to it. Chris, thank you so much for coming on on. I really appreciate it.

Well, thank you for your interest in the book, and I'm delighted to talk with you. Always delighted to talk with you, Karen. We talk a lot every week. Just for people who don't know, I'm on Chris's show on CNN on Saturdays, and I drive him crazy. That's really my job. You have this Countdown series. I want to know why Countdown. I need you to explain.

You had Countdown Bin Laden, Countdown 1945. Your daughter came up with this idea. She did. My daughter, Catherine, who was in the publishing business for a decade, and she probably could have made a lot more money, although I did give her a gift check for it. And the idea, I think, is brilliant, which is, you know, we think of history kind of from the present looking backwards, and that's not how people experienced history. They experienced it day by day, oftentimes not knowing what was going to happen or how it was going to happen. idea is to try to put you into the moment, the first moment, and then take you through the key moments as it proceeds to the climax. And so that's kind of the two words that I've heard are page-turner and thriller, and that's exactly the whole point of a Countdown series.

How do you pick? I mean, these couldn't be more different, bin Laden, 1945, the 1960 election. How do you decide which one is going to get counted down, I guess? Well, the reason I was interested in 1960 was because it was, first of all, the first election I was engaged in. I was 13 years old, so I was really interested in that. And secondly, because it, you know, had a beginning, a middle, and an end, a climax, which is one of the closest elections in American history. And also because I thought it had real relevance to 2020. And so, you know, you see what happens in 1960 sixteen it really sets what happened in twenty twenty on its head uh... because my argument is that's an election in nineteen sixty that may really have been stolen as opposed to twenty twenty

or are trump's talking about twenty twenty four but conversely the so-called loser in that case richard nixon decided that it was indeed that it was more important to observe the transition of power than to contest the election, and he went along with Kennedy's victory. Yeah, well, let's get into that. So one of the central claims of your book is that John Kennedy probably stole the 60 election. Now, this has been around for a while, the idea that his dad intervened in different states,

but it still might come as a surprise to a lot of listeners. Give us the big picture argument why Kennedy stole the election from your perspective. Well, you know, when you say Kennedy, it was really the entire Democratic machine and the two states that I focus on. And in Illinois, the head of the Cook County Democratic machine was Richard J. Daley. He was the mayor of Chicago, known as the boss. And there was a history in Chicago of election fraud, dead people voting, all kinds of things. And what happened in that election was that downstate Illinois, which is almost like the South and very Republican-oriented, came in first with a lot of the Republican vote, and then knowing what he had to come up with, that they stole the election,

that Daley and the Democratic machine had these outrageous, what the Chicago Tribune called, quote, fantastic pluralities. And there was one ward in Chicago where the vote was 10 to 1. It was 25,000 to about 2,500 Kennedy for Nixon. There was one precinct in another ward in Chicago where there were 80 votes cast and there were only 22 registered voters. So, you know, there was a lot of indications of election fraud and that the margin that Kennedy won by in Chicago, one, overcame the Republican advantage in the southern part of the state, and two, seemed kind of fantastic in terms of the vote majorities that Kennedy achieved rolled up in Chicago. Right. So you have that state, and then Texas was one I didn't correct. Talk about the difference.

Yes. Texas, well, and the significance of Texas is that Kennedy's running mate was Senator Lyndon Johnson, the senior senator from Texas, and also an enormously powerful man. He was the Senate majority leader, so one of the most powerful men in Washington. And again, there was a long history of election fraud. And so there were about 2.3 million votes cast in Texas, but fully half of them were paper ballots, 1.2 million. And the paper ballot, if you were voting for president, you had to mark who you were going to vote for, Richard Nixon or Kennedy or one of the other half dozen people on, but then you had to scratch out every other name. So you couldn't just vote for Kennedy. You had to scratch out Nixon and all the other third, fourth-party candidates.

And if you didn't do that, then it went to an election judge who were overwhelmingly Democratic to decide. And there were no set rules whether or not that vote was legit or whether it should be disqualified. Well, in the Republican areas with these Democratic election judges, about 40% of the Nixon vote was disqualified. But meanwhile, in the Democratic areas like Starr County, right on the border of Mexico, down in the southern tip of Texas, almost none of the Kennedy votes were disqualified. And Kennedy won by 46,000 votes. But if there are a ton of Nixon votes being disqualified paper ballots because they're not properly, you know, filled out, but not Democratic votes for Kennedy in the Democratic areas, you can easily see how Kennedy could have racked up this 42,000 vote advantage and won the 24 electoral votes. You're putting the sharp contrast to 2020.

We'll get to that in a second. But you say Nixon did the right thing by conceding, and Trump obviously didn't. The obvious difference is Trump actually lost, whereas Nixon might have had the election stolen for him. Why would a candidate like Nixon concede if their opponent steals an election? And how does the cheater taking over the presidency without contesting strengthen democracy? Well, I will tell you what Nixon's theory was, and you can decide for yourself whether or not it strengthens democracy.

But Nixon, I think there were several things going on. First of all, it was unimaginable at that point that you contested an election for president. Number one, you know, the idea that you're going to go to the courts and that the country isn't going to know for weeks or months who the president is if it was to go up through the courts. The second thing was the fact that we were at the height of the Cold War, and Nikita Khrushchev was the head of the Soviet Union. Nixon knew Khrushchev. He'd gone to Moscow on a trade mission when they had a model home as part of a trade exposition in Moscow in 1959, and he'd gotten into a debate, you know, not a two-minute, two-minute,

but kind of a verbal argument on camera with reporters there about whose system was better. And so I think that was it. That was one thing. Also, the deck was kind of stacked against him if he did take it to the courts, and the Republicans did. Nixon didn't, but Republican local officials did. They had tremendous difficulty beating the Democratic establishment in Illinois and particularly in Texas. And then the third thing that was a motivating factor for Nixon was he was a young man. Everybody talks about Kennedy, who was the youngest elected president. He was 42. Nixon was only 47. And I think he felt, you know, if I go through this and don't win and probably won't win, or even if I do

win, but it's going to label me as a poor loser, as a sourpuss for all time, and it'll end my political career. And I should have stolen it myself. They were smarter to say something like that. Well, you know, the interesting thing was Nixon had a very bad reputation because he'd been very much a slashing politician. In 1946, he comes back from the war. In 1946, he comes back from the war. He runs against an incumbent as kind of a sacrificial lamb in a house district in California, and he starts talking about his communist ties. And then in 1950, he runs against Helen Gahagan Douglas, who was a very popular Democratic politician, and he calls her the pink lady and says she's pink right down to her underwear. And so Nixon gets this nickname of, you know, very uncomplimentary of Tricky Dick

and was seen as kind of a dirty politician. He decides to go straight in the 1960 election and very much runs as a statesman and doesn't bring up a lot of the dirt that there was that existed about Jack Kennedy. And as a result, I think he felt that he had gone straight. He'd lost the election. He was always bitter about it. I think you can argue that what happened in 1968 and 74 and Watergate was kind of the offshoot of this. But in 1960, he played it straight, didn't contest it. And the biggest comparison between the two is January 6th. Yeah, we're going to get to that. So first, I want to go back when you were just,

I want to sort of lay this out with John Kennedy, most listeners know he was a serial adulterer, but they also may not realize he was also family friends with the infamous red-beating senator Joe McCarthy. He invited prominent white supremacists over to dinner at his house. He was uncomfortable around black people, and he palled around with mobsters. such a clean-looking figure compared to Nixon, who grew up relatively poor. He got a scholarship to study at Harvard as an undergrad, but he had to turn it down because it only covered tuition. He couldn't afford room and board. He was quite the opposite of JFK. So talk about the portrayals of both of those men then and later. Well, the only quibble I would have with you is a lot of the stuff you talk about, he certainly was a serial adulterer and was carrying on multiple affairs during the 1960 campaign, you know, unbelievably recklessly, including taking one woman, Judith Campbell, with whom he had an affair, to his home in Georgetown during the height of the primary campaign in 1960. You know, imagine that today. during the height of the primary campaign in nineteen sixty you know imagine that today

uh... and but a lot of that other stuff with the mob was much more his father than him joe kennedy who was rich uh... had made some of all of the uh... he was worth four hundred million dollars we estimate which would have been four billion dollars in today's money and he was the one who had a lot of the ties to the mob. So when you ask why was it that Kennedy seemed so clean,

is a lot of the dirty work wasn't being done by him. It was being done by his dad or his dad's henchman. And Kennedy was able to kind of skirt it and stay apart from it. And Nixon, you rooted for Nixon in 1960 when you were a 13-year-old. Talk a little about how he was perceived. Well, you know, he was, as you say, he was poor. He ended up going to Duke Law School. First of all, he was able to get into Harvard, but they couldn't afford it, so he ended up staying home and going to Whittier College. He was a non-athlete, but he tried out for the football team and basically spent the entire time on the bench. Then he gets

into Duke Law School, goes there, does very well. He was a very smart man, tries to get a job in one of the big white shoe Wall Street law firms, and he's just sort of not their sort. And he ends up having to go into private practice back in his home in Whittier, California, goes to the war, comes back, and as I say, has this political career so that in 1952, he's now the senator from California. And it's funny, one of Nixon's top aides when he was asked, and we talk about this in the book, count on 1960, why did they pick Nixon? They said, well, we were tired. It was at the convention. And he came from California. And the Republicans had had a very bad election

in the midterms in California in 1958. And they needed the electoral votes in California. As it turned out, they really didn't because Nixon beat Adlai Stevenson by a landslide. But at that point, they didn't know that. And they thought, well, there is this guy. He's tough. He can do the dirty work. And he's fiercely known for having fought the communists, you know, in the kind of red baiting of what was going on in the late 40s, early 50s. You know, he kind of hit the bell. We'll be back in a minute.

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Well, if you need a new pair, then Bombas has got you covered. I have tried Bombas myself. I actually got socks that you wear on a plane, so compression socks, and they were incredibly comfortable because usually compression socks, you want to like just die because they squeeze your legs so much. These squeezed your legs, but in total comfort, and they were very soft, and they looked normal, and I didn't look, you know, strange in them as you often do in other compression socks. I also wore one of their t-shirts, also incredibly comfortable. And it's also stylish. Bombas wants you to know about their mission, which is for every item you purchase, they donate

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that blended into the background. I hadn't noticed that until then. I was like, oh, yeah, look at that. I hadn't realized I was looking at that. And of course, Kennedy had a better fitting suit. It was a dark contrast to the background. Talk a little bit about that debate. It was a dark contrast to the background. Talk a little bit about that debate. Well, first of all, I will, but I'm going to tell you an anecdote that just happened. So I'm on the train coming back from New York on Friday, and the phone rings, and it's this voice I'm having trouble sort of understanding. And it turns out that it's the retired Senator Patrick Leahy from Vermont, who I know and is a lovely, lovely man. And he proceeds to tell me a story because he had heard me. I was on a show promoting

the book and talking about the Nixon-Kennedy debate. And he was a big Democrat even then. And he said that he was driving home to Vermont from someplace, I forget where, and he listened to the debate on the radio. And that he, you know, his reaction was, oh, my God, Nixon just killed Kennedy. It was terrible. And he gets home and he's got his Democratic friends and he's saying, oh, you know, we're dead. This is all over. And the guy, the people say, no, no, Kennedy killed Nixon. It was a wipeout. And so somehow, I guess he was able to get access

to a film, and he watches it, and he saw exactly that. So, I mean, this is a guy who literally first heard it on the radio and then saw the video of it. And why was Nixon so overconfident? Nixon, you know, he had a history as a debater. He'd been very successful in his political debates during his campaigns. He'd had this experience with Khrushchev in 1959 in this model home in a trade exposition in Moscow. And, you know, he'd been the vice president for eight years. And I think, although they were roughly the same age and he came into the Senate and Kennedy did in 52, Nixon did in 50, Nixon had a view and a lot of people did of Kennedy as kind of a rich boy lightweight and so he kind of took Kennedy lightly and didn't think that he was uh all that serious intellectually

or in term and or certainly in terms of experience now you you know you could argue because again there had been never been a presidential debate so it would have been much easier to skip that than now when there's been this long history for half a century. But Nixon was fine doing it, and the reason it was kind of an odd thing, and Eisenhower, in effect, said to him, don't do these debates, was because of the fact that one of Nixon's big advantages was the was because of the fact that one of Nixon's big advantages was the gravitas gap, the stature gap. He was the vice president for eight years. He traveled all over the world. He'd had this confrontation with Khrushchev. And Kennedy was a backbencher in the Senate who hadn't accomplished very much.

Frankly, he didn't even show up that often. He'd missed a bunch of votes. And, you know, so the idea of sharing a stage, it automatically was, unless you wiped him out, it was automatically going to lift Kennedy and diminish Nixon by putting them on equal footing. Well, in fact, the stature gap was completely gone, and coming out of the debate, Kennedy had a lead in the polls. Right. So in the final month, Nixon and Kennedy were in a mad sprint to the finish. Nixon was flying all over the country in order to fulfill his promise to visit all 50 states. And at one

point, he did a four-hour televised interview Q&A. But the press loved Kennedy, and he gave him a lot of access. He held big rallies and events with the Rat Pack and Hollywood celebrities. Talk about the media strategies and how they contrasted because he was doing a lot of new and fresh things compared to Nixon, who was sort of campaigning in the old style. Yeah. Well, one of Kennedy's biggest advantages, and this also came from his father, the old man, Joe Kennedy, is Joe said before the campaign in 1959, he says to Kennedy's younger brother, Bobby, who had a big job in the Senate and as a lawyer on a Senate committee, you're leaving that job and you're going to be Jack's campaign manager. And he puts together this incredibly modern campaign. Lou Harris, I'm sure a lot of people have heard of the Lou Harris poll, which has became a big thing. Well, at that point, he wasn't so well known, but he was one of the first private pollsters

for a politician. He was there, you know, getting all the latest data and basically saying, you know, this is what people are concerned about, voters are concerned about, so hit that point. He has Ted Sorensen, who was this fantastic wordsmith and who Kennedy called as his intellectual blood bank and, you know, has these great speeches that he makes and talks about America moving forward. And in his acceptance speech at the Democratic Convention, he invents this phrase, the new frontier. He also gets a press secretary by the name of Pierre Salinger. In fact, it was Bobby who came up with him, who's really kind of a great, you know, gregarious, hail fellow, well-met. And their idea of how to run the campaign was a charm offensive that, you know, Kennedy is attractive, he's glamorous, he's flying around in this private plane that his daddy bought for him called the Caroline.

And you give reporters access to Kennedy. And, you know, whether it was Kennedy or Bobby or Pierre, you know, you take people out for drinks. I'm not saying that they bought their affection, but people like covering Jack Kennedy. People like being around the Kennedys. They were glamorous. They were kind of pleasant to be with. They were, quote, nice to the press. And they liked them. And as a result, he got very favorable treatment.

And they were friends. I mean, Ben Bradley was a close friend. Everybody was close to these people. And conversely, Nixon, who had gotten such bad press, you know, from the days of Tricky Dick, it was sort of, you know, you get what you give, distrusted the press, didn't give them access to the candidate or to his top campaign staff, and distrusted them. And as a result, they viewed that as a much less attractive, you know, almost adversarial relationship and experience. So, you know, political reporters wanted to be on the Kennedy campaign, wanted to cover it, and didn't want to be with Nixon. And I think it probably, you know, it fed into their coverage.

So when you think about when, as it ended up, it was this tight race until the end, very tight. People don't realize how close it was because you think of Kennedy as the big winner all the time. But Nixon does not cry out, stop the steal, as Trump did. The day after the election at 1245 Eastern Time, Nixon's press secretary read Nixon's concession statement. Nixon accepted the results, even though his campaign manager told him the Democrats had stolen the election. And then he turns over power in the Senate where he presides. Talk a little bit, because he could have gone before TV cameras and said, there have been reports of irregularities in Illinois and Texas. We want them investigated. Talk a little bit about why he decided to do that. Well, and first of all, let me talk about how he did that. As you point out, Well, first of all, let me talk about how he did that. As you point out, Kennedy was ticked off that he didn't go on TV to concede. He had his press secretary, Herb Klein, read a telegram. But top advisors and their wives, they all go down to Key Biscayne. And on November, I forget, the 12th, I think it is, he's sitting at dinner at the Jamaica Inn in Key Biscayne.

And there's a phone call. And the maitre d' says it's some guy named Hoover. So he goes to the phone, and it turns out it's Herbert Hoover, the former Republican president who lost to FDR in 1932. And he says, I've just gotten a call from Joe Kennedy, and he thinks it would be great if you and Jack, the president-elect, met. Well, Nixon was suspicious of this, but he calls Eisenhower and says, what do you think? And Eisenhower says, I think you ought to meet with him. And so on November 14th, Kennedy comes down to meet with Nixon. But, you know, this has real significance. This is the winner meeting with the loser and the loser, in effect, acknowledging the winner.

And they have a very gracious hour. Apparently, you know, all we know about it, because it was just the two of them in the room, is what they said. Kennedy said he didn't offer him a position. Nixon said he did as a cabinet secretary, but Nixon said, I'm going to be part of the loyal opposition. But in any case, and coming out of it, Nixon says this points to the strength of our democracy that, you know, the winner and the loser can meet and we can have a peaceful transfer of power. Even more telling, there was a tough, young, up-and-coming investigative reporter for the New York Herald Tribune, which was the other paper in New York other than the New York Times. His name was Earl Mazo. And he decides that the election has been stolen.

And so he goes and investigates. And some of the things that we've talked about already, the vote fraud in Texas and the vote fraud in Illinois, he finds and he starts writing articles for the New York Herald Tribune. And they get some pickup in other newspapers. And he's in Washington one day, and he gets a call, and it's from Richard Nixon. And Nixon, as the president of the Senate, in addition to being vice president, has an office in the Senate, and he says, would you come over?

And Mazo thinks, one, Nixon's going to call and tell him, you know, thank you, congratulations, and two, maybe give him some tips to keep it up. And when he gets over there, Nixon says, listen, it's very interesting, and I understand it, but we can't not have a president in this country, and I want you to stop it. I want you to stop the investigation and stop the series. And Mazo is shocked because he thinks this is going to win me a Pulitzer Prize. I'm going to end up affecting who the president is and goes back to New York and intends to continue doing the series. And Nixon calls Mazo's bosses, the editors of the Herald Tribune, and says, hey, I talked to Earl. I don't know if he's going to follow this.

I want you to stop it. It's not good for the country. And, you know, that effort to investigate it is cut short. So you don't think of him like this, Nixon is this. That's what was interesting about this book. You think of him as the crook, right? And not just because of Watergate. He led one of the most corrupt administrations in American history. But in some ways, the book reads like a villain origin story. As you put it, one of the lessons Nixon took from 1960 was about the absolute need to win, whatever the methods, whatever the costs. Was there another scenario for Nixon?

Had he won? Oh, I think absolutely. It's funny you talk about that. And it is. It's sort of like the Joker origin story. I think, you know, I've thought about this a lot. And, you know, I talk about what the lessons that Nixon took from his defeat. And I guess I put defeat in quotes in 1960. And I think part of what he decided was that you won no matter how you won and no matter what the cost was.

And I tell a fascinating story that I have an odd connection. In 1968, Nixon is running for president again in 1968 against Hubert Humphrey. And this was the height of the Vietnam War. And it again is a very, very close election. It ends up being an all-night election. And at one point, John A. Farrell, who wrote kind of the definitive biography of Richard Nixon, tells a story that it's six in the morning, the morning after the election, and that it's coming down to Illinois again. Whoever wins Illinois is going to end up

winning the election. And that the report is that the vote is late coming in from Cook County. And Richard Daley, who'd been the mayor in 1960, is still the mayor in 1968. And this story, I didn't know. The word comes back, the vote is coming in late from Cook County in Chicago, meaning he's waiting to see how the vote comes from downstate, and then he'll manufacture enough votes to win it. And that Pat Nixon, Nixon's long-suffering wife, goes into the bathroom and throws up. Well, my father enters into this story because at about one or two in the morning, he had covered Nixon. This is Mike Wallace, but go ahead. Yeah, Mike Wallace in 1968. He had covered his campaign in the primaries.

And now he's on the set with Walter Cronkite and all these other people on election night for CBS News. News, and at about one or two in the morning, when the vote is very slow coming in from Illinois, he calls the Waldorf Astoria, which is where Nixon and his top advisors were spending the night, a big hotel in New York, and asked to speak to John Mitchell, who was then his campaign chairman, and he gets Mitchell on the phone, and the guy telling the story is Dwight Chapin, who was Nixon's body man, the man who kind of put him to bed and woke him up in the morning. And he says, Mitchell is saying, yep, Mike, that's right, yes, you're right, yeah. And you put it out there that, you know, when they put in some returns from Chicago, we'll put in some returns from downstate. And so my father, and now this part of the story, I learned at that time from my father, my father hears this from Mitchell, and he's gotten the say-so from Mitchell,

tell the world. So he goes on the air and says to Walter Cronkite and the millions of people watching CBS News at that hour, I just spoke to John Mitchell, and he basically says that they are not going to release the returns from downstate, the Republican areas of Illinois, until Richard Daley releases the returns from Cook County. And, you know, we're not going to make the same mistake of giving them a number to match and beat. And Daley starts releasing the returns in Northern Illinois, and Nixon ends up winning by about 160,000 votes, the state of Illinois. And it's those electoral votes and sort of poetic justice that put Nixon over the top and elect him president of the United States. But sort of made him the man he became

in a lot of ways. Well, yeah, I think one of the things that you hear in, first of all, in the Watergate tapes, the tape system that Nixon had set up in the Oval Office and a variety of other rooms in the White House, is how bitter he still was eight years later, and even as president, how bitter he still was about what Kennedy and the Democrats had done to him in 1960, and, you know, is complaining about it and complaining about Jack Kennedy and how the press still, obviously, Kennedy has been assassinated by this point. You know, the myth of Kennedy and how the press still, obviously, Kennedy has been assassinated by this point, you know, the myth of Kennedy and what a warm person he was. And he says, you know, what a cold SOB he was. And, you know, and then as the tapes go on, it becomes clear

that he was going to do whatever it took to win re-election, you know, with the full power of the government in 1972, and that leads us to Watergate. We'll be back in a minute. Support for On with Kara Swisher comes from Anthropic. Thank you. tool worth harnessing. But exactly how do you get started? Claude from Anthropic may be the answer. Claude is a next-generation AI assistant built to help you work more efficiently without sacrificing safety or reliability. Anthropic's latest model, Claude 3.5 Sonnet, can help you organize thoughts, solve tricky problems, analyze data, and more, whether you're brainstorming alone or working on a team with thousands of people, all at a price that works for just about any use case. Thank you. team was founded in AI research and built Claude with an emphasis on safety. To learn more, visit anthropic.com slash Claude. That's anthropic.com slash Claude. Mike Gitlin. Through the words and experiences of investment professionals, you'll discover what differentiates their investment approach, what learnings have shifted their career trajectories,

and how do they find their next great idea. Invest 30 minutes in an episode today. Subscribe wherever you get your podcasts. Published by Capital Client Group, Inc. Do you feel like your leads never lead anywhere and you're making content that no one sees? Published by Capital Client Group, Inc. you which leads are worth knowing, and makes writing blogs, creating videos, and posting on social a breeze. So now, it's easier than ever to be a marketer. Get started at HubSpot.com slash marketers. Every episode, we get a question from an expert. I think you'll like this one. It's a little long. Let's hear it. Hey, Kara. Jake Tapper here. Chris's book is awesome. Really, really amazing. You write in detail about the bizarre love triangle, quadrangle, trapezoid, whatever it is, the John Kennedy, President Kennedy and Frank Sinatra and Sam Giancana, the mobster had all of whom were familiar with a lady named Judith Campbell, Judith Campbell Exner. How do you assess Kennedy's peccadilloes, not just that one, but all of his irresponsible, if not criminal behavior?

There obviously was a book written not long ago by a woman who alleged that he essentially raped her when she was, I think, a White House intern. How much does this matter, not in terms of whether or not he should have been prosecuted or anything, but like in terms of how we now understand the modern presidency and the fact that he was so awful with women, so reckless with women, so adulterous, so promiscuous. What does it say to you, not just about his lack of character, but beyond that, his presidency? Did he legitimately expose himself to blackmail? How much did he subject our nation to risk? Well, that is a very smart question from a very smart fellow. Well, let me back up a little bit. Joe Kennedy was an infamous philanderer, carried on open affairs, you know, despite being in this, you know, supposedly wonderful, high Catholic marriage with Rose Kennedy,

but carried on open affairs, and the Kennedys kind of saw it, and I think, you know, kind of had a sense of, you know, the right of the Lord, the Dua de Senor, that, you know, somehow they were entitled to this. So, to get back to Jake's point, in February of 1960, Kennedy's traveling through the West. He makes a stop in Las Vegas, and he's buddies with Frank Sinatra, who's a big liberal and likes Kennedy and knows Joe Kennedy. And they all have dinner together, and Frank introduces him to a former girlfriend of his named Judith Campbell, who was a very attractive woman, you know, kind of an Elizabeth Taylor lookalike, and Kennedy begins a very hot and heavy affair with Judith Campbell. It becomes even more reckless because

Frank Sinatra also introduces Judith Campbell to a man named Sam Flood. Well, Sam Flood is an alias. His real name was Momo Salvatore Giancana, Sam Giancana, who was the head of the outfit, which is what the Chicago mob was called. I mean, this guy was a stone-cold killer, and the Kennedys ended up doing business with Giancana and taking money, some ill-got money, and giving it to the mob to spread around in some of the tough primaries that Kennedy was in, in Wisconsin and especially in West Virginia in the spring of 1960. And also, there were some unions at that point that were pretty much controlled by the mob, like the Teamsters. And Giancana has his people put the squeeze on the Teamster, the heads of the union, including Jimmy Hoffa, to, you know, get out the vote for Kennedy

in the general election. So, there is this unholy, as Jake says, not triangle, but kind of quadrangle of Jack Kennedy, Frank Sinatra, Judith Campbell, and Sam Giancana. I mean, it's one of the reasons that this book, Countdown 1960, is so fascinating. Yes, the parallels to 2020 are so interesting, but it's a great story in itself, a great political story, also a great kind of melodrama with sex and the mob. And I mean, I'll tell you one quick story. In West Virginia, it's funny, but we don't talk about this enough, but maybe the biggest single factor in this election was the fact that Kennedy was a Catholic, and in 1960, the idea of a Catholic president was unthinkable. There had only been one Catholic

nominee ever, who was Al Smith, who ran in 1928 against Herbert Hoover and got wiped out, and there was still a lot of anti-Catholic feeling in the country. Sure, especially in West Virginia. Well, at one point, Francis Cardinal Cushing, or Richard Cardinal Cushing, I'm sorry, who was the head of the Archdiocese of Boston, he gets all of the money, all the offerings that people give when they go to church on Sunday in the whole Archdiocese of Boston, and he gives the money to Joe Kennedy. Joe Kennedy then writes a check for even a little bit more of that to the Archdiocese. The Archdiocese gets, so they're covered, they get all the money that they would have gotten from the offerings. Joe Kennedy gets

a nice tax deduction. The money, untraceable cash, is given to the mob and other Democratic people in West Virginia, and it is spread out to a lot of the Protestant preachers and pastors in West Virginia to get them to support Kennedy, a state that is 95% Protestant, only 5% Catholic. And one of the reasons we know this is because Cushing, years later, Kennedy was in a real fight with Hubert Humphrey, the senator from Minnesota, for the nomination. Cushing brags to Humphrey years after the fact about this deal, tells him about it and says, it was good for the church, it was good for the preachers in West Virginia, and it was good for the candidate, Kennedy. Right. Incredible. Man. And we think politics is interesting today. I know. Let me finish up talking about that. Just a few questions

about the comparisons, which you just referenced. In 2021, after Trump's lies about election fraud, Republicans introduced over 500 bills that restricted voter access in Texas. The attorney general recently had police conduct a series of raids on Latino voting rights activists, and the Trump campaign has said it will have tens of thousands of people watching the polls in 15 states, which sounds a little like voter intimidation. Talk about the comparisons to now, what's happening from your perspective to this, because that's a dirty election, 1960. It feels dirty everywhere, whether it's the mob, whether it's the Catholic Church, whether it's, you know, bribery, etc., etc. Well, I mean, first of all, just take an example. The difference between, if you want sort of the

climax of the difference between the two, take January 6th, which by the Electoral Count Act is the day when the vice president certifies the counting of the vote. We all know what happened on January 6th, 2021. Trump goes to the ellipse. He speaks to this mob. He tells them, well, I mean, it's a crowd, but he says, we're going to march down and we're going to fight like hell. And if we don't fight like hell, we're not going to have a country. The mob goes down. They invade the Capitol. Mike Pence escapes barely with his life.

And now we know from the filing from Jack Smith, Trump's reaction to that is, so what? Well, in 1961, the vice president presiding over the election of John Kennedy is Richard Nixon, because that's who does it, the vice president. And he goes to the House, and he says, you know, this is the first time in 100 years since Abe Lincoln was elected and beat that vice president, John Breckinridge. This is the first time in 100 years that the vice president has to preside over the counting of the electoral vote of his opponent's victory and his defeat, and then he proceeds to count the votes. There's even a

fight about Hawaii because it was up for grabs, and Nixon rules that the Kennedy victory in Hawaii should be granted, not, you know, sent back to the state. And then he proclaims that, you know, that Kennedy has won, that he, Nixon, has lost, and that this shows the strength of democracy. You know, I just think that in the end, you know, there were a lot of other reasons for it, and maybe there were some states that the Republicans stole, and, you know, maybe there was, you know, this sense of this is going to be a bad thing for my career long term if I contest this. I just think that there was – the bottom line is that there was a sense of the power and sacredness of democracy and the idea that the winner wins, the loser loses, even if he didn't really lose, and that he observes and enacts the peaceful transition of power. And since 2021, and I have to say for somebody who grew up and has been through this for a long time, for more than 60 years, you know, that's unthinkable now, the idea that we wouldn't have,

you know, that the rules of my entire life in politics have gone out the window since 2021. And, you know, regardless of whether Trump wins or loses in November, you know, it's going to be a mess. And as you say, there are going to be all kinds of questions about voting judges and voting, you know, voting observers and whether there was intimidation. And, you know, there'll be all kinds of claims as there were in 2020 and 2021 about, you know, where the votes counted. And, you know, what are the things that's going to happen if this is a close election? And I hate the idea of it. Remember, it's not election day. It ends up being election week because, you know, you've got a state like Pennsylvania. And let's say Trump is, as he was in 2020, was in the lead just legitimately because more Republicans vote on the day of the election while more Democrats tend to vote, you know, mail-in ballots.

And those are counted afterwards. And, you know, you get this sort of red mirage where it looks like the Republicans are winning. And then as the mail-in vote perfectly, legitimately is counted, the Democrats start closing the gap and maybe they pass and win. It's going to be a mess. It's just going to be a mess. But one of the things, what's changed is this idea of an existential election. And now, Elon Musk spoke at the Trump rally last weekend. He said President Trump must win to preserve the Constitution.

He must win to preserve democracy in America. A lot of Republicans feel that way, while many Democrats think Trump would be a mortal threat to American democracy. If we talk about democratic principles, why is it better for a candidate who had an election stolen from them to concede than allowing the cheater to take the, you know what I mean? It's interesting. He's speaking out, and at the same time, in speaking out, he's creating false narratives about institutions, right? Yeah, I mean, that's certainly a legitimate point, Cara. You know, I guess all I can say is in 1960, I don't think the country could have handled it. You know, I mean, the idea – I mean, we were in – it's pre-Kennedy assassination. It's pre-Vietnam. It's pre-Watergate.

I mean, it's so many things. And, you know, as I understand America in those days, it's free the civil rights, yes, the movement, and we talk about that in the book that the Greensboro Four and Martin Luther King and, but it was such, so much more an innocent country. And, you know, as I look back on it, I'm just not sure the country could have stood an all-out fight over the presidency and, you know, going to federal courts and repealing this and going to the Supreme Court, which incidentally was pretty liberal at the time, so it probably would have sided with Kennedy as well. Right, right. with Kennedy as well. But, you know, I just don't know that the country could have gone through it at the height of the Cold War and, you know, the concern that Russia was going to attack us, that who the leader of the free world, who the president was, would have been up in the air for weeks or

months. You know, I think you make a decent point that maybe in the interest of truth, Nixon should have fought it. But, you know but I just don't think that the country could have handled it. So talk about country not handling it today. If Trump loses in November, can our electoral system handle the stress of a Trump-stop-the-steal 2.0 movement? Well, you know, it depends. I mean, he certainly did everything he possibly could in 2021,

and 60 lawsuits were filed. Trump won just on a technicality that didn't affect any of the vote count and certainly didn't affect the results in any state. You know, the system held. The Attorney General, system held. The Attorney General, Bill Barr, you know, goes to Trump in December and says, you know, I've looked into all of this and it's all bullshit. You know, you have a variety of people in various states, a variety of judges in various states, a majority, not unanimous, but a majority of the House and the Senate doing the right thing in voting on January 6th to vote down these challenges. But, you know, you can't be sure that it would happen. And the answer is, I guess, that if the guardrails held, we'd get through it. But if the guardrails didn't hold, and, you know, let's say that you had judges in a lot of these places start to say no, actually. And, of course, you know,

they're kind of trying to, the Trump people are, to create a situation. I mean, now this new rule in Georgia that the millions of votes, they're all, you know, where you've got machines that are much more efficient and much more accurate, that you're going to have to have a hand count. You know, you're ensuring that there are going to be arguments about this for days, if not weeks. And, you know, frankly, the one thing I pray for, and I'm really, I'm not going to say that I want one person to win or the other, is I just hope it's a clear election, that it's not close. I mean, frankly, 2020 wasn't close. Biden won by 7 million votes. He had over 300 electoral votes. He needed 270. That wasn't close, and it still was

kind of a mess. You know, I really hope that this, you know, God forbid people talk about this being 270 to 269 or 280 to 260, whatever. You want this election to be decisive, whoever wins, because either way, if it's close, and even if it isn't especially close, we're not going to know on election day or maybe even election week. It won't be assumed that, you know, this person is the president and that person is not. I mean, although the Biden campaign, 44,000 votes in three states, it was a little close. It was about as close as Trump's victory over Hillary Clinton was, where I think it was 70,000 votes in electoral votes. Clinton, of course, won by 3 million. But if 70,000 vote change in a few states would have switched the

electoral vote and she would have won. So if we did just a thought experiment, Trump somehow steals the election from Harris in November with all these different things. The networks call the race room, but she has evidence that he proved he cheated. Would it be better if she conceded and did the higher road that Nixon did? Man. No, you know, I think at this point, we're ready. I think we're in such a different situation

64 years later than we were in 1960. And, you know, it just isn't unprecedented. And, in fact, it's almost expected that there's going to be legal challenges and court cases. And January 6th is not going to be a simple formality but could be something of a battle. something of a battle. I mean, you've got J.D. Vance saying that if he had been the vice president instead of Mike Pence in 2021, he would have sent the votes back to the states to adjudicate, which may well have been one of the reasons that Trump chose him, that he wasn't going to pull a Mike Pence. No, I think, you know, as ugly as it is, I think we need to get to the truth. So no matter what, no matter what.

Yeah. I mean, it's horrible for the country. It's horrible that you even have to raise the thought experiment, Cara, but it's not unrealistic or impossible by any stretch. In fact, I think, you know, the odds of a challenged election in 2025 are, I think, more likely than not. So, last question, what lessons can we then learn looking at 1960 or the George Bush election or any of these elections or the last election we had or the one before that? What lessons can we learn from 1960 particularly going into what's happening right now? Well, you know, I do think there's something to be said. And, you know, as somebody who's all about the truth and facts, you know, to sit there and say, well, Nixon did the right thing.

You know, and look, it's not clear that Kennedy stole the election. There were some states that the Democrats didn't contest it because they won, but there were some states that, you know, they could have contested as well. So, you know, it could have gone either way. I wish, I guess the lesson I learned is I wish we could put the genie back in the bottle and have an election and, you know, not to say that you want vote fraud, but that the winner wins, the loser loses, the transition, the transfer of power goes on. a normal transition where the new president gets invited into the White House and all the new information is turned over to him and the cabinet departments all cooperate with each other. But that train has left the station. And I don't think, you know, people always talk about, is there ever going to be a post-Trump Republican Party? I certainly wouldn't say never, but it ain't going to happen anytime soon.

Right. And you would have to have landslides for that to happen, right, which don't happen anymore. Yeah. Well, no. That's right. I mean, they don't seem to happen. And I mean, and that, frankly, is one of the other things that I that I think is, you know, I would love us not to be in a 50-50. Look, there are elections when the person I supported has won and there are elections I've covered and where the person I supported and voted for is an American lost. But at least there was a consensus in the country. And,

you know, that's what you have in a democracy. You know, as a losing candidate once said, the voters have spoken, damn it. And, you know, you accept the will of the people and you move on. And in four years or two years, you get another crack at another election. I wish we could go back to that. It's going to be a while. Are we going to go back to that? Gosh, I hope so. All right, we'll end on that. Chris Wallace, thank you so much.

Cara, thank you. I really appreciate it. I must say, you're much nicer to me as a host than you are as a panelist on my show. On with Kara Swisher is produced by Christian Castro-Russell, Kateri Yoakum, Jolie Myers,

and Megan Burney. Special thanks to Sheena Ozaki, Kate Gallagher, Claire Hyman, and Kaylin Lynch. Our engineers are Raquan,

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