Kennedy Saves the World – Live From St. Martin
Episode Date: January 19, 2026
Host: Kennedy
Guests: Jimmy Failla, Guy Benson
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.
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.
2. Jimmy Failla's Presidential Twitter Moment
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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)
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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.
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)
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)
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)
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.
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)
Memorable Quotes & Moments (with Timestamps)
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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)
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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)
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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)
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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)
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
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.
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.