in: Character, Knowledge of Men, Podcast

• Last updated: August 1, 2022

Podcast #819: What Made JFK So Compelling?

Despite assuming the presidency from the 20th century’s narrowest election victory, John F. Kennedy captivated the American public’s imagination, even before his untimely death.  What was it that made JFK so compelling in his own time, and continues to contribute to his enduring appeal today?
We dive into the answer to that question by unpacking some of Kennedy’s personal qualities and complexities with Mark Updegrove, author of Incomparable Grace: JFK in the Presidency. We begin our conversation with how JFK’s upbringing and war experience shaped him. We talk about his leadership style while in office, how he intentionally cultivated his cool and appealing image, and what his wife Jackie added to that image. Mark explains what was behind Kennedy’s infamous affairs, and how JFK championed physical fitness despite being in tremendous physical pain himself. We end our conversation with the traits that worked both for and against JFK’s success as president.

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Brett McKay: Brett McKay here and welcome to another edition of The Art of Manliness Podcast. Despite assuming the presidency from the 20th century’s narrowest election victory, John F. Kennedy captivated the American public’s imagination even before his untimely death. What was it that made JFK so compelling in his own time and continues to contribute to his enduring appeal today? We dive into the answer to that question by unpacking some of Kennedy’s personal qualities and complexities with Mark Updegrove, author of Incomparable Grace: JFK in the Presidency. We begin our conversation with how JFK’s upbringing and war experience shaped up. We talk about his leadership style while in office, how he intentionally cultivated his cool and appealing image, and what his wife, Jackie added to that image. Mark explains what was behind Kennedy’s infamous affairs and how JFK championed physical fitness despite being in tremendous physical pain himself. We end our conversation with the traits that worked both for and against JFK’s success as president. After the show’s over, check out our show notes at

Mark Updegrove, welcome to the show.

Mark Updegrove: Thanks so much for having me, Brett.

Brett McKay: So you have a new biography out about John F. Kennedy called Incomparable Grace, and this is about his presidency. There’s a lot of biographies about JFK out there, what were you trying to do with this bio? How is it different from the other ones that you’ve seen out there?

Mark Updegrove: There hasn’t been a good biography on Kennedy’s presidency for quite some time, for a few years. I think you have to look at important historical figures from time to time through the lens of the times in which you’re living. So that was part of it. And part of it too, is that I wanted a brisk take on Kennedy’s presidency, something with a narrative that was as dramatic as the times that JFK faced during his presidency, so the reader could really understand why this president who was just in office under three years is regarded so highly, why his presidency still means something 60 years after his death.

Brett McKay: Well, we’ll talk about that. Hopefully we can answer that question, why he still matters. But why do you think, the 60 years after he’s been president, why do you think JFK still holds so much sway on our collective imagination?

Mark Updegrove: There’s something about the Kennedy image and that nods to the title, Incomparable Grace. JFK comes into the presidency and captures the imagination of the American people despite the fact that he only captured the presidency by two-tenths of a percentage point. 118,000 votes make the difference in John F. Kennedy being president versus Richard Nixon. So it was a very narrow victory, the most narrow of the 20th Century. But when he becomes president elect, the American people were swept up, not only in John F. Kennedy their soon to be president, but also the Kennedy family. His wife, Jacqueline Kennedy was cast this glamorous image of her own, his two small children and the larger Kennedy family, which is so vivacious and attractive. So that’s part of it. The image of Kennedy, I think, continues to captivate us. And I think moreover, Brett, he’s the way we want to be seen. He is visionary, he’s eloquent, he’s elegant, he’s rapidly ambitious, he’s youthful, he has this vigor. That’s the way we wanted to be seen when he was president, and I think in some ways, that’s the way we want our country to be seen today.

Brett McKay: And, yeah, let’s dig in because I hope by the end of this podcast, people will have kind of an idea of why JFK is so captivating because I think once you look at the details of his life, you start to understand what was going on there. So let’s start before he was president because as you said, his family, the Kennedy family played a big role in shaping his life and his political career. So as a boy, as a young man, what was Kennedy like? Did he showcase signs that he would eventually become the leader of the free world during post-World War II America?

Mark Updegrove: Probably not.

This is a kid who grew up wealthy during The Great Depression. His father amassed an enormous fortune during the greatest economic calamity ever to befall the country. So to say the least, JFK grew up in privilege. He also grew up very sickly and struggled with health issues throughout the course of his youth. His father, though, the ambitious Kennedy patriarch, Joe Kennedy, not only amassed a fortune, but also had political ambitions for himself and for his family. As far as he went, he really wanted to get in the… He thought himself that he might be the first Catholic president of our country. And eventually, as he accrues great wealth, Franklin Roosevelt owes him and asks him what he would like to do, and he says, “I’d like to be either secretary of the treasury or the ambassador to Great Britain in the Court of St. James.” And FDR reluctantly gives the post to the Catholic, Joe Kennedy, which was a first, to say the least, to have a Catholic be the United States Ambassador to Great Britain. But he becomes an isolationist at the beginning of World War II.

He espouses a position of isolationism, and that means that he’s out of favor, not only with Roosevelt, rather, but when we get into the Second World War, that he was on the wrong side of history more or less. So he more or less transfers those ambitions to his children. And again, I think the great hope for the family was Joe Kennedy Jr., the elder Kennedy’s namesake, who dies in the war. And when he dies, I think the ambitions that Joe Kennedy had for his eldest son are thrust at John F. Kennedy. And after the war, Kennedy throws his hat in the ring for political office, and that leads ultimately to his becoming president of the United States.

Brett McKay: Well, I think it’s important to flush out this dynamic between John F. Kennedy and Joe Kennedy Jr. Because Joe Kennedy, he was the favorite son. He was like the all star, the good looking guy, did well in school, athlete, then he had John Kennedy who was sort of like ehh… Didn’t think much of him.

Mark Updegrove: He was a bit of a screw-up versus his brother. There was this incredible competition between the two brothers. And at one point, they have a contest to see who can run fastest around the block. And they both go in separate directions. And whoever hits the base first wins. And the two are coming in, running toward one another, and neither will give way to the other. And eventually, they end up colliding. And Joe Kennedy wins the race, and John F. Kennedy ends up going to the hospital, which is almost a metaphor for what happened in their youth. Joe Kennedy got all the glory and achieved a great deal and John F. Kennedy ended up being frequently in the hospital because of health issues, not reaching the potential that his brother had reached.

Brett McKay: And then yeah. When John F. Kennedy heard that his brother died, he mournful said he understood what this meant. I think he said, “The burden now falls to me.” He understood, like, “Now, my dad’s ambitions, I have got to carry that now.”

Mark Updegrove: Yeah, and I think he felt a certain responsibility himself for carrying the torch of the next generation in some respects. Irrespective of his father’s ambitions for him, he had his own ambitions. And it’s important to note, Brett, that John F. Kennedy would not have gotten into politics if it didn’t suit him as well. It happened to suit his father’s ambitions for him and other members of his family. But it was also something that Jack Kennedy at that point in his life. He wanted to be, as he said later, relating to the presidency, he wanted to be in the center of the action. So for anyone who was ambitious post-World War II, it was almost instinctive to want to go to Washington. So you have these folks coming out of World War II off the front lines, coming back States side and wanting to make their mark on the world. And the way you did that at the time, the natural way to do that, was to get into elective politics and to go to Washington. So you have Richard Nixon, and Gerald Ford, and others almost instinctively throwing their hats in the ring after coming back from the Pacific theater or Europe in World War II.

Brett McKay: Well, before we move to his political career, something we often forget, people forget, is that Kennedy also, he served in World War II in the Navy. He had wartime experience. In fact, he wrote a book based off his wartime experience. How did his experience in World War II influence his leadership philosophy?

Mark Updegrove: He captained a PT boat, PT-109. And it was split in half by a Japanese torpedo in the Pacific. And at that point, John F. Kennedy really shows his courage and his leadership mettle. All of his crew members, two of his crew members die in the blast. But it falls to him to help his crew mates, those under his charge, to swim to an island. And there’s one of his troops who was incapacitated. And JFK puts his shirt in his teeth and he literally drags him to shore, where ultimately they are rescued. But this is a real leadership challenge for John F. Kennedy. And he steps up to the task. And I think it gives him much greater confidence than if he hadn’t gone through World War II.

Brett McKay: So he gets back from the war, in the ’50s, he begins his political career. Where did he get elected first? Was it representative then Senator?

Mark Updegrove: No. He makes himself a candidate for Congress in the Massachusetts district around Boston, and this is in 1946, and gets elected. He’s terrible on the stump, Brett. And if you look at the legacy of John F. Kenny, so much of it is around his rhetoric. He is a brilliant speaker. He captures one’s imagination. But initially, he’s pretty awkward on the stump. In fact, he says his father thinks he’s hopeless. But because of the power and prestige of the Kennedy family, he wins the election and goes to Congress, where immediately, he sets his sight from the lower chamber, the House Of Representatives, to the upper chamber, the Senate. And in 1952, in a very tightly contested race, ends up beating Henry Cabot Lodge, who was a very prodigious candidate. And so that leads to the eight years that Kennedy will spend in the Senate.

Brett McKay: And what was his career like as a Senator? Was he productive?

Mark Updegrove: I think in both the House and Senate, he didn’t have a particularly illustrative tenure. He was more or less a back bencher in the Senate. I think at that point, as soon as he got to the Senate, he was focused on the next rung, and the presidency. He was trying to determine how he might become the vice presidential nominee of his party on the ticket in 1956. That comes close to happening. When it doesn’t, he sets his sight on being the presidential candidate in 1960 and ends up getting the nomination.

Brett McKay: So he wasn’t an LBJ when he was a senator. He wasn’t good at the back out… The back door deals and things like that?

Mark Updegrove: Quite the contrary. I don’t think he had interest in the legislative process. LBJ was a creature of power. And he wielded it so effectively as perhaps the most powerful senate majority leader in the history of our nation, certainly the most powerful of the 20th century. He had an instinctive sense of things. The legislative process really didn’t interest Jack Kennedy all that much. In fact, the most noteworthy thing he does during the course of his years in the Senate is write the book, “Profiles In Courage”, which his father, through his purse strings, helps to make a commercial success, and also through his political connections helps to make a Pulitzer Prize Winner. So in the mid ’50s, Kennedy writes “Profiles In Courage”, it wins the Pulitzer Prize, and that helps to elevate the stature of young John F. Kennedy.

Brett McKay: So he seems like he has a personality more suited for the executive as opposed to the legislative branch. Because you highlight here that you said he wanted to be in the presidency because that’s where the action is at. And he wanted the ability to get things done with a minimum of bureaucracy and organizational inefficiency. So you just want to be able to say, “I want to do this” and you get it done.

Mark Updegrove: That more or less, yeah, I think what he says, when Ben Bradley, who was then working for Newsweek and would ultimately be the editor of The Washington Post, asks him why he wants to be the president, he likens it to being Johnny Unitas, who played for the Baltimore Colts at the time, the NFL’s champion team, and Unitas is the quarterback, and that’s what Kennedy wants. He defines that as the center of the action. Unitas could play other sports, other positions, but to be quarterback for the Baltimore Colts at that time, that’s the peak of football, and for Kennedy being the President of the United States, the world’s biggest superpower, in the top position, that was about as high as you could get, and that would be the center of the action. To your point, he didn’t have to get consensus in many cases from different people in the houses of congress, there are many things you could do with the bully pulpit of the presidency, there were many things you could do through executive order. You didn’t necessarily have to go through the sausage-making process that is needed to crank out a law.

Brett McKay: Something else that you point out in the book is when Kennedy took office, assumed office, he was inheriting this from Dwight D. Eisenhower, and Eisenhower, he really… He effectively re-organized how the presidency was run, he had the Chief of Staff and all that stuff. Kennedy comes in and he kind of starts mixing things up again, what was his leadership style, or what was his organizational philosophy when it came to his presidency?

Mark Updegrove: Dwight Eisenhower was a military man and his administration was organized like a military man would organize something. It was stratified, and there were different ranks, and you’d talk to the people below you and they’d talk to the people below them and etcetera, etcetera, etcetera, and it was a traditional triangular structure with the person at the top and more people at each layer going down, but extraordinarily stratified and hierarchical. Kennedy didn’t want that. Kennedy wanted to talk to whoever he wanted at any time, and he would poke his head into the offices of those two, three levels below him to get their take on things. He wasn’t much interested in meetings, he wasn’t much interested in briefings, he kind of felt his own way around the presidency much, I would add, to his detriment. It wasn’t the best way to approach the presidency. There were many advisors who tried to get to him who couldn’t get to them, and at a certain point in his presidency, after he stubbed his toe a time or two, and we can talk about those early failures, his advisors come back to him and say, “You have got to help us out here, you have to adhere to some kind of structure in the White House. You might not want to hear this, but it’ll be better for your presidency, and it’ll be better for us as well.”

Brett McKay: And that’s a recurring theme throughout the book, is that Kennedy, he would stub his toe, he would make mistakes and big ones, but he always seemed to learn from them.

Mark Updegrove: Yeah, I think that’s right. And I mentioned JFK capturing the imagination of the American people upon his inauguration, we can all remember his soaring inaugural rhetoric, “Ask not what your country can do for you, ask what you can do for your country.” And it really galvanizes the country. Americans really start thinking beyond themselves, about what they personally can be doing for their country. The Peace Corps, which is enacted in Kennedy’s first year is a manifestation of that. Us thinking about the greater good and doing something big for our country, something important, but his first few months were not particularly successful. The Bay of Pigs, which is a failed incursion of Cuba by a former Cuban nationalist goes awry. It’s supported by the US government, although clandestinely, and it is an enormous failure.

Brett McKay: Over 100 Cubans die, over 1000 are taken capture… Captive rather, and it’s a big black eye for the administration, but it says something Brett, that when this happens, this huge fiasco in world view, that John F. Kennedy’s approval rating subsequent to that is an astounding 83%. Americans doubled down on presidency at a time in the Cold War when we knew the Russians were watching and might be emboldened by a foreign policy failure by the United States. So Kennedy never sees an approval rating higher than that, that he sees after this huge mistake, the Bay of Pigs quagmire. Importantly though Nikita Khrushchev, Kennedy’s counterpart in the Soviet Union, is watching there and believes based on that, and a disastrous summit with the Russian premiere just two months later, that Kennedy is weak and can be exploited, and I think that leads to Kennedy’s greatest crisis, which happens in 1962, the Cuban Missile Crisis.

And we’ll talk about that here in a bit. But before we do, we talked about this mystique around Kennedy, this image that he projected, and this was intentional, he was aware of it, he was very aware of the image he was showcasing to the population. I think he saw himself… I think I’ve read, it’s weird in the United States, our president is not only like a parliamentary figure, he’s in charge of getting stuff done, but he’s also the figure head. In a lot of other countries, the figure head is separated from the parliamentary person, so like in the UK you have the Queen, who’s the figure head, then you have the Prime Minister. United States it’s one. It’s the President. So he was very aware that I represent our country. What did he do to project the image that he wanted the public to have of him?

Mark Updegrove: It’s funny because Kennedy doesn’t consider himself a natural politician. He comes from a political stock, including his maternal grandfather, Honey Fitz, the very colorful mayor of Boston who is the typical… The stereotypical baby-kissing name-knowing back-slapping politician. That is not John F. Kennedy. Kennedy was cerebral, he was cool, and while he thinks he’s, in his words, the antithesis of a politician, which in many respects he is, if you compare him to that archetype…

That his maternal grandfather personified. But he also knows, in his words, that he fits the times. Part of that is because of the medium of television, the dominant medium of the age, he knows he’s suited to television. He has a cast, a sort of glamorous image. He’s handsome, he’s fit, he’s eloquent, as I mentioned earlier, there’s a certain elegance. There’s a way he carries himself that is incredibly alluring, and he knows that, that’s part of the reason he did get the presidency. You probably don’t have John F Kennedy in the presidency, but for the presidential debates with Richard Nixon, who looks very pasty-faced versus the very vital John F. Kennedy, and it’s probably that image alone that Kennedy casts that gets him the presidency in 1960. So, so much of cool, so much of image is ineffable, it can’t be quite explained. And I think that’s probably true with Kennedy, but there is a certain cool that he exudes this incomparable grace, as my title would suggest, that is just captivating not only among Americans, but citizens of the world.

Brett McKay: Yeah, and like you said, it’s ineffable, but he understood that it’s there. And there’s instances you highlighted in the book where both him and his brother and some of the aides, they would always be watching or reading the magazines or the newspaper articles. And anytime there was some instance where they kind of spoke badly, they’re like, Hey, they’d pounce on it like, “We’re going to put on the PR and we’re going to change the conversation about this.”

Mark Updegrove: No question about that. He knows the power of photography, the Power of Life magazine at the time, there were far fewer media properties at the time. You had three networks, ABC, NBC, CBS, you had a few news magazines, Time, Newsweek, US News, you had Life Magazine, which was almost the People magazine of its day. There weren’t many, and John F Kennedy was determined to dominate them as much as he could. But he also knew the power of the moving image, as per my comment about television, but also the still image and how pictures of his young family could be so advantageous politically. In fact, when Jackie Kennedy left the White House on occasion, he would bring the kids into the Oval Office and have them photographed and he would say, “Don’t tell Jackie.” [chuckle] He knew the power of that, the image of him as a young, vigorous father of these very attractive young children. The Kennedys knew when they were playing touch football on the grounds of Hyannis Port, but that was probably going to be in the magazines, and that would be enormously beneficial for them, and in what was the equivalent of page six at the time? So yes, Kennedy is definitely aware of image and how important that it is in his political trajectory.

Brett McKay: We’re going to take a quick break for a word from our sponsors. And now back to the show.

Well, speaking of an important part of his image, you mentioned his wife, Jacqueline Kennedy. What role did his wife play in his political career?

Mark Updegrove: Well, I think first and foremost, she was a support to him. She wanted him to be a great president. She saw the greatness potential in him and wanted him to realize that in the presidency, some of what I tried to debunk in this book is the Kennedy mythology, the sort of this Camelot image that comes after Kennedy is assassinated, and that’s really Jacqueline Kennedy trying to tell the story of her late husband and trying to romanticize that presidency. She too knew the power of image and wanted to help make him a great president. She also knew her own value in terms of the image that she projected. When the Kennedys first go abroad, they first stop in France, and Jacqueline Kennedy was a Francophile and a Francophone, she could speak French. And that was very alluring to the French people who could be famously fickle. But Charles de Gaulle, the French president, fell in love with her, and she helped enormously in casting the right image to the French people. She created the White House Historical Association to build the White House into a thriving place for arts and culture and to make it the most beautiful house in the world, and she was the right person to do that. She had an image for how the White House should look and made a huge difference in making that the envy of the world in many respects.

Brett McKay: Yeah, that was my takeaway from the book, that Jacqueline had a really fine tuned political instinct that it paired well with her husband.

Mark Updegrove: Yeah, I think that’s right. She was… She didn’t love the political spotlight. She didn’t love politics. She was certainly not a natural politician. I would say, when he was a senator, she felt like she was a detriment to him. She was disadvantageous because she wasn’t the typical political wife, just as Jack Kennedy wasn’t the typical politician, but she didn’t contrive a personality of somebody who was relatable. And that probably did hurt Kennedy when he was a senator. However, when she became first lady, that became tremendously advantageous. Her class, her refinement, her style of sensibility, helped to elevate the role of First Lady and the White House as the center of power for the American government.

Brett McKay: Something I didn’t know about Jackie and John Kennedy is, they experienced a miscarriage and a stillbirth. How did those personal tragedies affect JFK and his wife?

Mark Updegrove: Well, the miscarriage comes in the mid 1950s, and Kennedy is on holiday in Capri and actually doesn’t come back when he finds out that the child has died, that, that it has been stillborn and Bobby Kennedy is the one who ends up tending to Jacqueline Kennedy. That’s one of the… That reflects the blemish on Kennedy’s character. He was not a particularly good or faithful husband. And in fact, George Smathers, who is a friend of his in the Senate, tells him to, “Get his ass back to the United States and tend to his wife if he has any presidential ambitions whatsoever.” And Kennedy reluctantly leaves his European holiday and goes back to be by his wife’s side. By that time, the stillborn child has been buried because of his brother being…

Taking charge in his brother’s absence, so it’s hard to understand how Kennedy could be so callous and so selfish and reckless, but that’s an example of it. The Kennedys also lose a son, Patrick, in the last year of Jack Kennedy’s life. In August of 1963, Jacqueline Kennedy gives birth to a child prematurely named Patrick, and the child dies after two days, at that point, Kennedy is by his wife’s side, and I think that that episode, losing a child, not only bound the Kennedys closer to one another, but bound the American people to Jack and Jacqueline Kennedy as well.

Brett McKay: So something you tackle on the book is Kennedy’s womanizing, which he’s infamous for, were you able to figure out what was behind that?

Mark Updegrove: I think there are several factors. Number one, Kennedy comes from a father who was a rampant womanizer himself. He had open relationships with a number of folks when, for instance, split his time between the East Coast and Hollywood where he was a principal at one of the studios, RKO, which he helped to found and he lived openly with Gloria Swanson, one of the great movie stars of the silent and then later sound era. He was a quintessential philanderer, and so JFK, to a large extent, learns at the feet of the master in a way. It sort of comes naturally based on the example that his father sets. Moreover, though I think it was a means of keeping score in the very competitive Kennedy household. They would brag about their conquests as indelicate as that may have been. I also think that JFK wanted to seize every moment of life possible, I think he saw his own mortality, he could see the fragility of life, and as he says frequently, he wants to make the most of every moment and for them, that was the ephemeral thrill of a conquest, and those things are major blemishes on his character, but I think those are the reasons that he’s such a rampant womanizer.

Brett McKay: Yeah, how do you make sense of it, how do you incorporate that into the rest of Kennedy?

Mark Updegrove: He was very… Like so many great men, he’s compartmentalized, that’s just a part of who he is. It’s the most reckless and unattractive part of him. Listen, it’s part of the zeitgeist at the time too, so many lawmakers at that time in our history were having affairs, either secretively or openly in Washington, it was a pretty common thing. A Kennedy goes [0:28:19.3] ____, you can’t just rationalize that as being part of the Washington zeitgeist. There’s one thing that I think is particularly unforgivable, and that is the relationship he has with a 19-year-old intern named Mimi Beardsley to whom loses her virginity to Kennedy just a week into her tenure, and he really just objectifies her in a way that just simply can’t be explained or forgiven. This young, vulnerable girl being exploited by the President of the United States. At one point, Kennedy asks her to perform a sex act on one of his friends and aides, and that just is absolutely unforgivable.

Brett McKay: Yeah, yeah. So you kind of… He compartmentalized that in his head?

Mark Updegrove: Without question. And I think he thought maybe it was his right… A divine right of kings in a way, to do what he wants… He looks at British Royalty, one of his favorite books has to do with the British aristocracy at a certain point in time when they would do their duty in London during the course of the week and then in weekends go to Manor houses and sleep with each other’s wives and girlfriends and those sorts of things. It was almost the right of the aristocracy to behave in that way, and I think Kennedy probably believed that as well.

Brett McKay: So something maybe a lot of people don’t know is that he spent his life in immense, physical pain. What were his ailments that he had?

Mark Updegrove: Well, he had Addison’s disease, one, and that was something that he had battled throughout most of his life, and then he had chronic back pain, and there is a cocktail of drugs that he would have on any given day in his tenure as presidency that it is absolutely staggering. It is amazing how many injections and how many drugs Kennedy was taking to keep his pain at bay and to keep his Addison’s disease from affecting his performance. That said you don’t really see any examples of the drugs or the womanizing for that matter, affecting his duties in discharging the responsibilities that come as President of the United States.

Brett McKay: Yeah, he was incredibly stoic about his pain. He’d be in pain, but he just wouldn’t say it… He wouldn’t talk about it. And in fact, he had aides who said, “I never heard Jack Kennedy ever complain about his pain.”

Mark Updegrove: His closest friend who knew him since his days in high school, said he never heard him complain about it, to your point. It’s amazing. So there is a certain stoicism, a certain courage that comes from Kennedy, who you know is suffering, in fact, there are times when I think we’ve seen these wonderful broadcast clips of Kennedy greeting his kids when he steps off Marine One, the Presidential helicopter on South Lawn, and they come bounding out onto the South Lawn to greet him, and he reaches down and pats them on the back, but he can’t pick them up because he has this back brace that prevents him from reaching down, and even if he could, he probably wouldn’t do it because it could further aggravate his very painful back. So that pain, those medical conditions were a constant companions for Kennedy throughout the course of his presidency.

Brett McKay: Do you think that experience with pain was partly what drove his push for physical fitness? I’m gonna say it the way he said it, “in vigor.”

Mark Updegrove: Vigor [chuckle] Vigor was a word that sort of defined the Kennedys, and if we only knew the medical regimen that Kennedy was under in order just to get out of bed every day, it would be staggering. But yes, I think the Kennedys sort of embody that in many respects. They were extremely active, playing sports in some, many ways, sports was a way of excelling in the very competitive Kennedy family. That’s the way you proved yourself at a certain point in time, but they also sailed and they were extraordinarily active. So physical fitness, I think, was a natural part of the Kennedy brand. At one point, Kennedy demands of his cabinet that they all lose 10 pounds. [chuckle] He’s really serious about people being at their very best.

Brett McKay: It seems like he… Because his own health, it was a struggle, he didn’t take vigor for granted. Because he struggled with his health, Kennedy understood how fundamental it was to everything better than anyone. And so that’s why he really championed the idea of sound mind and a sound body and how important health and fitness was for the individual, but also for a citizen. And for that reason, he made that a national effort. He was one of the… He was the guy who really spearheaded the presidential fitness test.

Mark Updegrove: The President’s physical fitness test, that’s exactly right, which many of us took in high school.

Brett McKay: Yes.

Mark Updegrove: That comes from Jack Kennedy.

Brett McKay: And then he also revived the 50 mile march, which became a thing like after in the ’60s and ’70s, people used to go for walks for 50 miles. And I think Bobby Kennedy, he did the 50 mile hike in loafers in the winter.

Mark Updegrove: That’s exactly right. That’s exact, as one preppy might, but that’s precisely right. It’s funny because Kennedy, again, he looks so physically vigorous. We had no idea of the illnesses that he was battling but he really does personify the look of physical fitness.

Brett McKay: So we mentioned, early in his presidency he had the Bay of Pigs invasion, that was a fiasco. He got his butt kicked at a summit with Khrushchev and even admitted that like after it was over, he’s like, “I just got my butt handed to me by this guy.” But then he has his moment as one of… And it’s like a really… It’s like his greatest diplomatic victory, it was the Russian missile crisis. What did he… What lessons did he take from his previous whoopings that he was able to apply to navigate the Russian missile crisis effectively?

Mark Updegrove: Well, he sees in the Bay of Pigs fiasco that his military advisors are very jingoistic, they are very hawkish. They want to get out there and they want to wage war. They want to get into the heat of battle. And he thinks they’ve been very impetuous and they’ve steered him in the wrong direction with the Bay of Pigs. By the same token, he goes before the American people and says that success has many fathers, but failure is an orphan, but at the end of the day, I’m the commander-in-chief, and the mistake of this lies with me. I’m the one to blame here. And the American people, again, as I mentioned earlier, forgive him, partly because he is so humble in that moment and resolves to do better. So I think he learns to keep the military at a distance to a certain extent. He learns to keep very close counsel, which he does during the course of the Cuban Missile Crisis. 13 harrowing days when we find out that the Soviet Union is shipping troops and nuclear warheads to Cuba, which would represent the first time that Soviet weaponry is in the Western Hemisphere just 90 miles from American shores, which means that Washington could be hit by a nuclear weapon within 20 minutes. So this becomes the central crisis of Kennedy’s administration staring down the Soviet Union, ensuring in every way possible that they withdraw, that those nuclear warheads and troops from Cuba so that we don’t have a presence of Soviet military in the Western Hemisphere.

Brett McKay: And what do you think was the trait or quality that allowed Kennedy to handle that crisis and leaned itself generally to what other success he had as president?

Mark Updegrove: Part of it is equanimity, and in the Cuban Missile Crisis, you really see that he meets with Dwight Eisenhower in the second of his two-transition meetings before becoming president. And in that meeting, Eisenhower, is enumerating all of the trouble spots throughout the world, including Vietnam and Cuba and Berlin and other places. And Kennedy listens to all this and you could see the relief in Eisenhower’s countenance to put these problems on the desk of another president. And he leaves that meeting and says to an aide, “I can’t believe he can stare into the face of disaster with such equanimity” [chuckle] but yet it’s equanimity that helps to save Kennedy in the Cuban Missile Crisis, which is as close as we have ever come to a nuclear exchange, to a nuclear war. That is the most dangerous hour in mankind’s history when we’re so close to the possibility of a nuclear exchange, but it’s Kennedy’s cool in those moments. Hence, in going back to the ambiguous title of the book, Incomparable Grace, there’s an incomparable grace that he shows during those desperate hours.

I mentioned Profiles in Courage before Kennedy’s Pulitzer Prize winning book. And he uses a line from Hemingway, his favorite author, to define what courage is. And Hemingway said that courage is grace under pressure. And that’s what Kennedy shows during the Cuban Missile Crisis, a certain grace under pressure, which is based on the equanimity that he exudes, the calm, he doesn’t do anything rash. He doesn’t back himself into a corner, he’s not impetuous. He’s not hungry for revenge, he waits out Khrushchev, they have a series of exchanges, and ultimately the crisis is resolved through a quid pro quo that we have. The world wouldn’t know this until much later, but the Cuban Missile Crisis is resolved because we tell the Soviet Union that we will withdraw nuclear warheads from Turkey, which is in the backyard of the Soviet Union, if they will withdraw their missiles from Cuba. So the Soviets ship those missiles out of Cuba. And six months later, very quietly, the Americans… We Americans take our missiles out of Turkey.

Brett McKay: Did he have any qualities that worked against his success, that caused him to blunder?

Mark Updegrove: Well, I think it was that impetuousness that we talked about early on, with the Bay of Pigs, there was a certain recklessness. I think there was probably a certain hubris… No man is prepared to be President, but Kennedy was probably a little brash when he came in. He became humble very quickly, to his credit, and he learned from the mistakes that you talked about. We talked about that disastrous summit with Nikita Khrushchev in June of 1961, which I believe, emboldens Khrushchev to ship those missiles to Cuba eventually. But Kennedy realized… And that’s how I start the book, with what might have been Kennedy’s weakest moments, when he has been, in his word, savaged by Nikita Khrushchev in these meetings. But again, he is resolved to do better. And Kennedy works hard to become a better, a more humble, more effective leader.

Brett McKay: What lessons do you hope readers take away after reading your book? And how do you hope their idea of Kennedy’s changed, when they close the book?

Mark Updegrove: Well, I don’t know what idea they have before they come to the book, Brett, but I hope they see the power of leadership. I think, in particular, Kennedy shows us the power of rhetoric. The power that words can have at crucial times. I quote Clement Attlee, who was the successor to Winston Churchill as Prime Minister of Great Britain, who said of Churchill’s great rhetorical ability during the Second World War, which helped to sustain the British people, that… He says, “Words, at great moments, can be deeds”. And you see that with Kennedy. Words at the great moments of his presidency almost become deeds. So, when Kennedy elevates civil rights to a moral issue, which he does in his a speech around civil rights in June of 1963, that elevates the cause. That becomes an almost an inflection point in the struggle for civil rights in this country. When he goes to Rice University and says, “We choose to go to the moon, and to do the other things.” He makes that adventure a uniquely American proposition and rallies American around the very ambitious, and very expensive, effort to take Americans to the moon. When he stands at the foot of the Berlin Wall, and says, “Ich bin ein Berliner. I am a Berliner, because I am a free man, and as a free man, I say to you, I am a citizen of Berlin”… That rallies the world around the cause of freedom and liberty, in the face of the Soviet threat of tyranny.

Brett McKay: Well, Mark, this has been a great conversation. Where can people go to learn more about the book and your work?

Mark Updegrove: Well, they can certainly go, they can buy the book online and at bookstores, and… I certainly hope they do, and I am the President and CEO of the LBJ Foundation, and we do a lot of work on the presidency here, including a podcast called With the Bark Off: Conversations on the American Presidency.

Brett McKay: Fantastic. Well, Mark Updegrove, thanks for your time. It’s been a pleasure.

Mark Updegrove: Brett, thanks so much for having me. It’s been a delight.

Brett McKay: My guest today was Mark Updegrove. He’s the author of the book, Incomparable Grace. It’s available on and bookstores everywhere. You can find more information about Mark’s work at Also check out our shows at You can find links to our resources, and we delve deeper into this topic…

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