Kennedy Saves The World Live From St. Martin

Summary

Kennedy Saves the World – Live From St. Martin

Episode Date: January 19, 2026
Host: Kennedy
Guests: Jimmy Failla, Guy Benson

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Episode Overview

This episode of "Kennedy Saves the World" brings a laid-back, humorous conversation with comedian and Fox News host Jimmy Failla and commentator Guy Benson. The trio dives into personal anecdotes, the interplay between comedy and politics, NFL coaching chaos, media behind-the-scenes, and sports predictions—all with trademark wit and playful banter. The main theme revolves around the value of good-natured humor in a polarized society and the lived experience of media personalities in the political and sporting limelight.

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Main Discussion Points & Insights

1. Setting the Scene & Lighthearted Banter

• Kennedy jokes about being in an exotic Zoom background, playfully fooling Jimmy about being on an island getaway.
  • [00:10 – 00:29]
  • Jimmy: “At first I thought you guys had went on like an island getaway without me… But now that I know you guys are just at the Rainforest Cafe… I feel better.”
• Sets a light, self-deprecating tone to the group dynamic.

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2. Jimmy Failla's Presidential Twitter Moment

• Jimmy recounts learning, in an airport bar, that the President had tweeted a compliment about his show.

  • [01:08 – 03:38]
  • Failla's initial skepticism and comic paranoia:

    “I usually need multiple sources before I report something, so I was looking for a second person drinking at the bar before I just ran with the story.” (01:25, Jimmy Failla)

  • On the significance of the tweet:

    "The line was, Jimmy Fail, his opening monologue was great. Very funny guy. But Then he wrote, also wonderful wife.” (02:31, Jimmy Failla)

  • Jokes about needing to check his taxi license and wondering if the tweet is really about his wife Jenny more than himself.
  • Affably admits being “the biggest mooc” and credits his wife for his public dignity:

    "She so classes up what I’m doing...I lean in proudly to the fact that I am the highest functioning level of white trash we’re never going to employ here at Fox." (02:59, Jimmy Failla)

• Guy and Kennedy respond:

  • Guy: “The term better half is often overused, but it absolutely applies in your case to her.” (03:38, Guy Benson)
  • Humor about the unpredictability of public praise.

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3. Comedy, Politics, & the Art of Good-Natured Roasting

• Jimmy reflects on writing jokes about the President and the satisfaction in a politician embracing satire:
  • [04:15 – 06:48]
  • "The fact that he's praising comedy, that makes fun of him, you know, delicately...the fact that he’s highlighting the type of comedy is cooler because it means there is a market out there for, like, good faith humor. It’s just humor.” (05:18, Jimmy Failla)
  • Discussion of Trump's self-deprecating appearances:

    “He was in a Comedy Central roast of himself…‘What’s the difference between Donald Trump’s hair and a dead raccoon? ... A dead raccoon doesn’t have $5 billion in the bank.’ Pretty good.” (05:37, Jimmy Failla)

  • On the limits of comedic responsibility:

    “When someone comes up to me on the street and [says], ‘Jimmy, we got to save this country’...I’m 49, I play video games, okay? The country’s long gone.” (06:23, Jimmy Failla)

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4. Behind-the-Scenes in Media and Shows

• Appreciation for writing and production effort behind topical monologues.
  • [07:01 – 09:10]
  • Guy lauds Jimmy's "Guy on Guy" segment for its outrageous fun and popularity:

    “They like the ridiculousness because it’s such an off ramp. And obviously you’re brilliant at it and it’s really funny.” (07:29, Jimmy Failla)

  • Insights on late-night writing teams versus individual workload:

    Kennedy: “Colbert may have, what is it, 80 writers?”
    Jimmy: “They have about 20… I'm paying myself. I have to write the whole fricking thing.” (09:00 & 08:42)

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5. NFL Coaching Carousel & Sports Culture

• The gang dissects the recent tumult in NFL coaching, with a comical but empathetic take on fired coaches.
  • [09:34 – 11:27]
  • Jimmy explains the unfair dismissal of Bills coach Sean McDermott after a controversial call:

    “The Bills receiver caught a ball… the Broncos defensive back ripped it out of his arms… But if that catch was ruled a catch, the Bills are attempting a game winning field goal on the very next play... He's now out of a job. I like, legitimately feel bad for him.” (09:47, Jimmy Failla)

  • On misplaced fan sympathy for wealthy sports figures:

    “Sports is the only thing in the world where people feel bad for people who have much better lives than them.” (10:53, Jimmy Failla)
    "Aaron Judge is going to a home to a supermodel in a mansion. You're going home to a jar of hand cream at your mom's house." (11:01, Jimmy Failla)

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6. NFL Coaching Hires and Culture Shifts

• Discussion moves to Giants' and other major NFL teams' choices in hiring coaches—tying this to the concept of organizational ‘relevance’:
  • [11:27 – 12:54]
  • Jimmy: “That relevance juices an entire organization because you have a guy who you know has won before, you know, he’s respected...It brings additional attention.” (12:10, Jimmy Failla)
  • Guy and Kennedy riff about Kennedy's own influence as a “paradigm shift” at Fox and make tongue-in-cheek comparisons to sports transitions.

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7. College Football Tangent & Playful Predictions

• Continues with quips about college football coaching (Chip Kelly, etc.) and makes group predictions for the NCAA Championship.
  • [13:08 – 14:23]
  • Guy believes Indiana will win, citing their dominant performance:

    “They destroyed Alabama, made Alabama look like Alabama would make Indiana look in years past.” (13:44, Guy Benson)

  • Kennedy wraps up with a cheeky send-off:

    "Fernando Mendoza wants to go into his hometown and say, you know, in soft, sweet, Christian terms, suck it." (14:12, Kennedy)

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Memorable Quotes & Moments (with Timestamps)

• On being publicly noticed:

  “Most people come up to me on the street and they’re like, ‘Hey, Jimmy Failla, you got change of a 20?’...How can I make you useful?” (05:59, Jimmy Failla)

• On winning praise for comedy:

  “This is real validation...There is a market out there for, like, good faith humor. It’s just humor. I don’t want to be in charge.” (05:19, Jimmy Failla)

• On NFL sports culture:

  “Sports is the only thing in the world where people feel bad for other people who have much better lives than them.” (10:53, Jimmy Failla)

• On the jealousies and jabs of media friends:

  “So it’s not enough that you guys had to...show me this fake background party that I’m missing out on. I now need to be subjected to your marital criticisms. Good for you.” (03:48, Jimmy Failla)

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Key Timestamps for Important Segments

• 00:10–00:29: Opening banter, island Zoom backdrop prank
• 01:08–03:38: Jimmy learns about the President’s tweet; reflection on the moment
• 05:05–06:48: The value of non-partisan late-night comedy and roasting
• 07:01–09:10: Behind-the-scenes on writing comedy for TV versus late-night with large staffs
• 09:34–11:27: NFL “coaching carousel”; why fans feel for millionaire coaches
• 11:27–12:54: Giants’ new coach, culture, and the importance of “relevance”
• 13:08–14:23: College football predictions, playful banter to close

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Tone & Style

This episode is quintessentially lighthearted, self-deprecating, and irreverent with true camaraderie among the participants. Kennedy, Jimmy Failla, and Guy Benson mix genuine insight on media and sports with playful digs, light swearing, and pop culture references. The tone is quick, witty, and welcoming—even as the topics span politics, celebrity, and serious sports stakes.

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In Summary

“Live From St. Martin” is not an actual tropical escape, but an escape into the lighter side of media life. Listeners get a behind-the-scenes look at navigating public attention, the evolution of political comedy, and why a sense of humor—and humility—might just be our best survival skill. The episode stands out for its easy rapport, authentic laughter, and celebration of finding levity in both everyday absurdities and news headlines.

Transcript

[Jimmy Failla]

Foreign.

[Kennedy]

Hello, and welcome to this episode of Kennedy Saves the World. Today I've got two special guests. Jimmy Fala and Guy Benson.

[Jimmy Failla]

Wait, what?

[Kennedy]

Hi, Jim.

[Jimmy Failla]

Yeah, so where are you guys exactly? That looks like a pretty exotic location.

[Kennedy]

Long island.

[Jimmy Failla]

With a palm tree in the back. Oh, I. Yeah, I noticed. Now it's a backdrop. I get it. Yeah, yeah, it's one of those sophisticated zoom back. At first I thought you guys had went on like an island getaway without me. I didn't know I was feeling FOMO fear of margarita ing out. But now that I know you guys are just at the Rainforest Cafe having a brunch special, I feel better.

[Kennedy]

Now you can. So, Jim, it was so much fun on your show Saturday night, but you had a pretty big fan watching the show. Tell me about it.

[Jimmy Failla]

Listen, I was in an airport bar Sunday morning, and the guy across from me was the one who told me I was ordering a drink, as I am wont to do. And he was like, hey, Jimmy Fail, the President just did a tweet about you. So, you know.

[Kennedy]

You think he was lying?

[Jimmy Failla]

No, I usually need multiple sources before I report something, so I was looking for a second person drinking at the bar before I just ran with the story.

[Guy Benson]

Did you have a flight or were you just there?

[Jimmy Failla]

Yeah, trying to. Trying to find some lonely stranded passenger who missed a connection. So anyway, I had a flight to catch, and so I went and tracked down the source material before I told anybody in my life. Because how. First of all, as cool as it is to have the President treating a compliment about comedy, which is not something he does a lot of, you know, if you make a point he agrees with or, heaven forbid, disagree with, you're going to hear about it. So my initial reaction was I hadn't seen the tweet. He's just like, yeah, the President tweeted about you.

[Kennedy]

Now what did I say?

[Jimmy Failla]

Yeah, that was. My initial reaction, was like, do I still have my taxi license? Is it valid? Because. And he deserves credit for this. And we'll get there. I make fun of him a lot in my monologue.

[Sponsor/Ad Voice]

Okay?

[Jimmy Failla]

I don't make fun of him as like, Orange Cheeto. Jesus shouldn't be in charge. I do comedy for the point of comedy, you know? But so to his credit, he was praising a monologue that probably had five minutes of jokes about him and Tom Holman and everything else like that. So upon seeing the tweet, I was like, oh, this is amazing. The line was, jimmy Fail, his opening monologue was great. Very funny guy. But Then he wrote, also wonderful wife. How great that. Well, at which point I thought they might want to invoke the 25th amendment. Okay, we've all hung out with Jenny. I'm kidding. Jenny's great. That was the best part for me is that he did highlight Jenny Phela. She is great and I am. I truly mean this. She so classes up what I'm doing because I am obviously mean well and I'm fun and we hang out, but I am the biggest mooc we know. I'm the biggest mooc you know, I'm the biggest MOOC I know. Like, I lean in proudly to the fact that I am the highest functioning level of white trash we're never going to employ here at Fox. She dignifies it by coming along with that other classy, good time, good hearted Midwestern thing. So thank God for Jenny because I don't think tweet one happens without the content of tweet two, which is Jenny.

[Guy Benson]

And I think, like, the term better half is often overused, but it absolutely applies in your case to her.

[Jimmy Failla]

So it's, it's not enough that you guys had to, you know, kind of show me this fake background party that I'm missing out on. I now need to be subjected to your marital criticisms. Good for you.

[Kennedy]

We're not criticizing. We're lifting up Jenny.

[Jimmy Failla]

Yes.

[Guy Benson]

And we are dumbfounded that she married you, but it's a big win for everyone involved. Is it surreal to her to have the President posting about her on social media?

[Jimmy Failla]

Do you know what? Yes. You know what she said, which is so funny? She goes, she do me a favor and never book me on the show if you're going to criticize him. Because she could just as soon be like, Jimmy fail. His wife is a five. He's a failed comedian. Totally overrated. I don't know why Fox gave that guy a show. I mean, as you guys know, you know, this bull ride can turn in any direction in the pen at any time. And that's the part about it that's so unique. But honestly, I do mean this as a comic. The fact that he's praising comedy, that makes fun of him, you know, delicately. Because I'm not trying to, like, shift political perceptions with my jokes. When I'm making fun of the Democrats, I'm never going. And this is why you better not vote for them. And that's what the other host are getting wrong. So the fact that he also not.

[Kennedy]

Shoving a love hose up his honey hole.

[Jimmy Failla]

No, no, not. He's not into that he has this other thing with a feather. I'm kidding. But so stick with me, I think. And I really. This is real validation. This is what I really got from this. I do mean this. Okay. He grew up in an era of really good late night and probably genuinely misses the warmth of good late night, which is like, you just kind of know. It's like a roast. Nobody cares. And that's what I think we're missing the most.

[Kennedy]

He roasts everyone. He has a sense.

[Jimmy Failla]

He roasted himself. He was in a Comedy Central roast of himself. Do you want to know one of the jokes he told? This is a great joke. This is what he opened his. This is. At the time, he was a Celebrity Apprentice host, but he leaned right into all the rumors about his hair. And he goes, what's the difference between Donald Trump's hair and a dead raccoon? And he goes, a dead raccoon doesn't have $5 billion in the bank. Pretty good. Like, he leaned in. He owned it in both directions. But that's kind of what you're supposed to do. So the fact that he's, like, highlighting your comedy is cool if you're me, but the fact that he's highlighting the type of comedy is cooler because it means there is a market out there for, like, good faith humor. It's just humor. I don't want to be in charge. I tell you this all the time. When someone comes up to me on the street, not often, but once in a while, most people come up to me on the street and they're like, hey, Jimmy fail, you got change of a 20? It's not even like, I like you. It's like, I recognize you. How can I make you useful? But when someone comes up to me on the street and I like, jimmy, we got to save this country. I'm like, dude, if it is down to me, I'm 49. I play video games, okay? The country's long gone, so I don't know. I thought this was a win for all of us, not just me.

[Kennedy]

No, I thought. I thought it was. And I'm very happy that we were a part of your second year anniversary.

[Jimmy Failla]

Oh, it was a big. It was a big deal, man. I was.

[Kennedy]

Well, I was there in spirit.

[Guy Benson]

I was there the previous week, two weeks ago.

[Jimmy Failla]

Can we jump in? Guy has the greatest segment in the world. And Guy, we've refined it more since you were last on because we realized we're kind of producing it wrong. But Kennedy Guy comes on and does a segment called Guy on Guy where I just ask him about guys in the news, and he gives me a take. And it was like, would you pick this guy up in a taxi? Do you think he'd be annoying? And we're kind of just spitballing on what we think they're like socially. And, Guy, you have no idea how high this rates. It sounds crazy.

[Guy Benson]

Obviously, I'm rated again.

[Jimmy Failla]

Yes. And I like, again, specifically right at the C block, it pops up. And it's because they like the ridiculousness because it's such an off ramp. And obviously you're brilliant at it and it's really funny. And Kennedy, speaking of people who don't mind being made fun of, if you're gonna book Guy Benson on my show, you gotta want to get made fun of, because the three best jokes of the night were him telling me he shouldn't be on my show, as always.

[Guy Benson]

Can I just say one thing before you completely move on from the Trump post? Congratulations. Like, that is. That's, like, validating and amazing. And I think the other thing that's important just to, like, sit on and think about for a second, he wasn't just saying, like, hey, Jimmy Fail is a cool guy with a good wife. He specifically went out of his way to praise the content. Right.

[Jimmy Failla]

So that's.

[Guy Benson]

That's huge for you and for your team. So I feel like that's gotta be just such a fun. Not that you needed a morale boost aside from, like, having to work for you, but, like, I feel like it had to have been probably a good thing for the team as well to be like, holy cow. Not only are the ratings good, especially in the C block. And Guy. And Guy, the President, United States is watching, and he likes the mono. Right? Like, there's. There's several layers to that.

[Jimmy Failla]

Yeah.

[Guy Benson]

I.

[Jimmy Failla]

Someone said. I. They're like, you should give your writers a raise. I'm like, then I'm paying myself. I have to write the whole fricking thing.

[Kennedy]

I'm saying, I don't think people realize, like, I listen to you refining and writing your show after you've already written the monologue. So Colbert may have, what is it, 80 writers.

[Jimmy Failla]

They have a lot. They have about 20.

[Guy Benson]

You should absolutely agree. Be like, yes, the writers should get a raise.

[Jimmy Failla]

Just endorse it. Where's that writer money at? Guy Benson.

[Kennedy]

I am so unselfish. The writers get the raises. Don't go anywhere more. Kennedy saves the world right after this. This is Ainslie Earhart. Thank you for joining me for the 52 episode podcast series the Life of Jesus.

[Jimmy Failla]

A listening experience that will provide hope, comfort and understanding of the greatest story ever told. Listen and follow [e-mail] or wherever you listen to podcasts.

[Kennedy]

So, Jim, speaking of comedy, is there anything to laugh about with the coaching carousel of formerly employed NFL coaches?

[Jimmy Failla]

Yo, it is so crazy right now. I feel so. I actually legitimately feel bad for the Bills coach. Sean McDermott just got fired over a play that was literally probably the worst call in NFL history, if only because it not only was it not an interception, but they didn't even review it. Like he did what he was supposed to do in that, in that moment, the Bills receiver caught a ball as they were rolling over, the Broncos defensive back ripped it out of his arms. Now, that same play happened yesterday in a playoff game, was not called an interception. But the point is it's obviously an either way call at best. Sean McDermott called timeout, right? Just to give the refs time to like talk about it and go, maybe we should review this. They didn't review it. But if that catch was ruled a catch, the Bills are attempting a game winning field goal on the very next play. Instead, Denver, as the ball drives down the field and scores. He's now out of a job. I like, legitimately feel bad for him. He'll get another gig. And that's my favorite thing about this carousel though, okay? Everyone has gotten fired, which means I keep getting the same reaction from my friends. And this is guy, I think you'd agree with this. Sports is the only thing in the world where people feel bad for other people who have much better lives than them. You know what I'm saying?

[Kennedy]

That is so true. That is such a great point.

[Jimmy Failla]

The Yankees get knocked out of the playoffs. My neighbor Petey, I've told you this. Kennedy calls me up. I feel bad for Aaron Judge. He's such a competitor, he wants it so bad. I'm like, dude, Aaron Judge is going to a home to a supermodel in a mansion. You're going home to a jar of hand cream at your mom's house. I'm like, Aaron Judge should lead the press conference with I feel bad for you. As should Sean McDermott is the point. Don't look at me. I told you it was white trash on the way in.

[Guy Benson]

I'm not. Are you a Giants fan?

[Jimmy Failla]

Listen, I grew up a Raider fan of all people. But in my adult life, I root for whoever covers the spread. But I have a Giants take. Give me yours.

[Guy Benson]

I'm like Sort of a Giants fan, right? If I had an NFL, like, mediocre fan. I watch the games. I'm much more into college, so I'm a Giants fan. They've been awful. So I feel like the Giants have needed really good head coaching for a while here. And to have a guy who was just rock solid and consistent in Baltimore. Yeah, I guess they finally just want to throw up their hands. Like, you know, this isn't working anymore. We sort of timed out. I mean, maybe I'll eat my words in a year or two, but I feel like, like, just like finding a pot of gold for the New York Football Giants and John Harbaugh.

[Jimmy Failla]

Yeah, that's a big win because the other thing it gives their franchise is relevance. Yeah, that's the one thing about bringing in a big name coach. And that relevance juices an entire organization because you have a gu who you know has won before, you know, he's respected. It brings additional attention. It's the same. The Patriots, you know, basically Mike Vrabel, okay, took a 4 and 13 team to. They are on the precipice of going to the super bowl. And the personnel did not change that much from last year to this year. They just brought in a guy who was formerly successful at Tennessee, who had a relationship with the Patriots as a player, and it juiced the franchise. And there's something that can be said for a guy who comes in and literally changes the culture. And I think everyone would say that about me coming to Fox News.

[Kennedy]

No, it was a big deal. It was. It was a paradigm shift.

[Guy Benson]

I thought. I thought that was a subtle reference. And I think most people in America would have gotten it, too. You were talking about Northwestern hiring Chip Kelly as offensive.

[Kennedy]

Yeah. If you want to take your program, hire Chip Kelly.

[Jimmy Failla]

No, no.

[Guy Benson]

As an offensive coordinator. It's a great hire.

[Jimmy Failla]

He's a phenomenal hire. I think you guys and Chip Kelly are going to have 10 of the most exciting months of your life. And we wish him luck to wherever he goes next. He's the Lane Kiffin of coordinators.

[Sponsor/Ad Voice]

He sucks.

[Kennedy]

Everything about him sucks. Chip Kelly sucks. Okay, since we're talking about four's up, Bob Chesney is going to completely redefine that program. Very excited about it. Okay, last one, predictions from all three of us. Who wins the NCAA football championship tonight?

[Sponsor/Ad Voice]

Jim.

[Jimmy Failla]

My. Yeah, my heart is with Indiana all day.

[Guy Benson]

My heart is because I'm like a Big Ten loyalist, but my head is, too. They're a machine. They're steamrolling everyone. They destroyed Alabama, made Alabama look like Alabama would make Indiana look in years past, right? Like, not even close. Oregon, yeah.

[Kennedy]

So beat Oregon twice.

[Guy Benson]

Miami's good. Carson Beck's good. I think anything can happen, you know, like Penn State wasn't that good this year and Indiana almost lost them. Anything can happen, but I think it's iu probably pretty big.

[Kennedy]

Fernando Mendoza wants to go into his hometown and say, you know, in soft, sweet, Christian terms, suck it. And I think.

[Jimmy Failla]

And on that note.

[Kennedy]

I'm with you on that note. Hi Jim. This has been Kennedy Saves the World along with Guy Benson. Jimmy Fayla, I'm Kennedy. Listen ad free with a Fox News Podcast plus subscription on Apple Podcasts and Amazon Prime. Members can listen to this show ad free on the Amazon Music app. Oh, go ahead and leave me a review while you're there. I'd love to hear what you have to say. You've been listening to Kennedy Saves the World on the Fox News Podcast Network.

[Sponsor/Ad Voice]

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