Best Harry Cigar Podcasts (2025)

1
Inside the Resistance 2.0 | Rep. Jamie Raskin 38:42

2d ago38:42

38:42

Where is the Democratic “resistance” for Trump’s second term? Chief Playbook Correspondent Eugene Daniels asks Rep. Jamie Raskin, a longtime nemesis of President Trump’s and the current House Judiciary Committee ranking member, why the Democrats have been slow to counter the president’s aggressive governing, and what the plan is going forward to re…

1
Roy Wood Jr. on ‘Lonely Flowers’ and ‘Have I Got News for You’ 1:06:27

7d ago1:06:27

1:06:27

Larry is joined by actor and comedian Roy Wood Jr. and they begin their conversation by acknowledging Black History Month. Roy then breaks down his new CNN show ‘Have I Got News for You’ and opines on whether or not comedic "bubbles" will last under the new Trump administration (5:41). They then pivot to his recently released stand-up special on Hu…

1
Trump and the GOP Congress’s fork in the road I Rep. Lisa McClain 33:58

9d ago33:58

33:58

House Republicans are facing tough choices on reconciliation, party unity, and whether or not to look the other way when President Trump steps on their authority. In this episode, House GOP Conference Chairwoman Lisa McClain gives the scoop on House leadership's hours-long meeting with the president on Thursday, and why she thinks that the House GO…

1
'I don't think they're going to get the battle that they want.' Inside Trump’s first clashes with Congress and the courts 47:56

16d ago47:56

47:56

Trump has moved aggressively to define his second presidency. POLITICO’s top reporters have thoughts on where he’s going, and how Congress, Democrats and the courts may try to stop him. Eugene Daniels is a Playbook co-author for POLITICO. Rachael Bade is the Capitol Bureau Chief and Senior Washington Columnist for POLITICO. Ankush Khardori is a col…

1
Juanita Tolliver on ‘A More Perfect Party: The Night Shirley Chisholm and Diahann Carroll Reshaped Politics’ 1:01:09

21d ago1:01:09

1:01:09

Larry is joined by journalist and MSNBC political analyst Juanita Tolliver to discuss her new book, ‘A More Perfect Party: The Night Shirley Chisholm and Diahann Carroll Reshaped Politics’. They begin their conversation by talking about what inspired Tolliver to write about the legendary political fundraiser and shining a light on the many influent…

1
Chuck Grassley’s Trump 2.0 vibe check 33:51

23d ago33:51

33:51

Sen. Chuck Grassley (R-Iowa) is the longest serving current U.S. senator and currently chairs the Judiciary Committee, which will have purview over President Donald Trump’s immigration policy. He is also the former chairman of the Senate Finance Committee, which has jurisdiction over tax policy — two big seats for the coming reconciliation bill. On…

1
Laura Coates on ‘Laura Coates Live’ 1:06:29

28d ago1:06:29

1:06:29

Larry is joined by CNN Anchor and Chief Legal Analyst Laura Coates, and they begin their conversation by talking about Laura’s stylistic approach to the interviews she conducts on her show ‘Laura Coates Live’. They then break down the defamation case between ABC News and Donald Trump and discuss the reasons why there is currently a general mistrust…

1
Jason Smith on who’s getting the “candy” in reconciliation 33:20

30d ago33:20

33:20

Ways & Means Committee Chairman Jason Smith joins the show to elaborate on his vision for reconciliation, how he’s working with the diverse factions within the GOP to achieve it and why he believes he will prevail in passing “one big beautiful bill” with major tax cuts. Eugene Daniels is a Playbook co-author for POLITICO. Jason Smith is the Chair o…

1
RaMell Ross on ‘Nickel Boys’ 1:08:53

1M ago1:08:53

1:08:53

Larry weighs in on the L.A. fires. He’s then joined by writer and Academy Award-winning filmmaker RaMell Ross to discuss his newest movie ‘Nickel Boys ’(8:33). They begin their conversation by talking about how the project came together, RaMell's experimental inspirations, and the screenwriting process with co-writer Joslyn Barnes. Next, they dive …

1
The Art of the Deal (Greenland edition) 32:25

1M ago32:25

32:25

Michael Froman — former U.S. Trade Representative, Deputy National Security Advisor and current president of the Council on Foreign Relations — joins Playbook co-author Eugene Daniels to discuss the state of affairs in the world that Trump is stepping into, how world leaders are watching and reacting to Trump’s every word and what he thinks Trump w…

1
Power Play: How the world's political power brokers are gearing up for 2025 26:06

2M ago26:06

26:06

Out with the old and in with the new or in the case of 2025, it’s back to the future with the return of Donald Trump to the White House. As America and her allies prepares for Trump 2.0, what can we be certain of in an increasingly unpredictable and fractious world? In the final episode of Power Play this year, host Anne McElvoy is joined by POLITI…

1
Alan Zweibel on the Early Days of ‘Saturday Night Live’ 1:05:50

2M ago1:05:50

1:05:50

Larry is joined by Emmy Award-winning writer and producer Alan Zweibel to discuss his experiences working on ‘Saturday Night Live’ during its first few years on the air. Alan begins the conversation by sharing his feelings about the 50th anniversary of ‘SNL’ and detailing the anatomy of a good joke. Larry and Alan then talk about Lorne Michaels’s o…

1
Does Trump have Justin Trudeau dancing to his tune? 37:36

2M ago37:36

37:36

One thing Donald Trump loves to say is that he knows how to make a deal. And even for our allies, sometimes the “Art of the Deal” can feel like a shakedown. Ask NATO about that, and you’ll get some nods. But lately, Canada is the ally that’s been caught in Trump’s line of sight. The president-elect has been trolling Prime Minister Justin Trudeau on…

1
How big business is making its relationship with Republicans great again 39:46

2M ago39:46

39:46

Donald Trump’s Washington is going to be packed with heavyweights from big business such as Elon Musk, Scott Bessent and Howard Lutnick. But the U.S. Chamber of Commerce, which represents traditional business interests in D.C., has recently found itself estranged from its longtime allies in the Republican Party. On this episode of Playbook Deep Div…

1
Emily Chang on ‘Posthuman’ and ‘The Circuit’ 56:17

2M ago56:17

56:17

Larry is joined by technology journalist Emily Chang to talk about her Bloomberg Originals limited series ‘Posthuman’, and her podcast ‘The Circuit’, which features interviews with influential figures in the tech industry. They begin their conversation by discussing the inspiration for ‘Posthuman’, which delves into humanity’s connection to artific…

1
How to dethrone a Democratic ranking member 35:58

2M ago35:58

35:58

Generational change. It’s been a hot topic for Democrats ever since Joe Biden announced he’d run for a second term, and it's been picking up steam this past week as House Democrats pushed aside aging ranking members on key committees in order to make room for some younger leaders. In this episode, Playbook co-author Eugene Daniels speaks with Rep. …

1
Timothy Shenk on ‘Left Adrift: What Happened to Liberal Politics’ 1:11:09

3M ago1:11:09

1:11:09

Larry is joined by writer and historian Timothy Shenk to discuss his newest book, ‘Left Adrift: What Happened to Liberal Politics’. They begin their conversation by talking about why they think the Democrats failed with their messaging in the 2024 election and what the rise of Trumpism means about American culture today. Next, Shenk shares the hist…

1
How the Senate GOP is tempering Trump 2.0 48:40

3M ago48:40

48:40

Sen. Kevin Cramer (R-N.D.) weighs in on President-elect Trump’s cabinet picks, the news of former Rep. Matt Gaetz’s withdrawal from attorney general consideration and his takes on some of the incoming president's most controversial ideas. Rachael Bade is a Playbook co-author for POLITICO. Kevin Cramer is the junior senator from North Dakota. Kara T…

1
Ep. 224- Morgan Dawson: Unstoppable 1:21:20

3M ago1:21:20

1:21:20

-As the holiday season approaches, the guys sit down with influencer and cosmetics business owner Morgan Dawson. The California native opens up about her journey and how consistently having the same dream at a crucial part of her life ultimately led her to start building what is now a powerful and profitable community through social media. Now the …

1
S.E. Cupp on ‘Off the Cupp’ 1:25:02

3M ago1:25:02

1:25:02

Larry weighs in on the results of the presidential election and the future of the Democratic Party. He’s then joined by political commentator and host of the new iHeartRadio podcast ‘Off the Cupp’, S.E. Cupp, and they begin their conversation by sharing their reactions to Donald Trump winning the presidential election (18:01). They then examine the…

1
A vanquished Democratic senator’s warning 29:16

3M ago29:16

29:16

Sen. Sherrod Brown (D-Ohio) opens up for the first time about his recent defeat, and what he thinks his experiences holding a senate seat in reliably red Ohio since 2006 can teach fellow Democrats attempting to redefine the party’s brand. Eugene Daniels is a Playbook co-author for POLITICO. Sherrod Brown is the senior senator from Ohio. Kara Tabor …

1
Ep. 223- Chris Richardson: From the Music Business to the Money Business 1:16:07

3M ago1:16:07

1:16:07

-The guys take a dive into the world of financial services as they sit down with Chris Richardson of PHP. The Birmingham native opens up about how his time in the military and a few near-death experiences in the music business ultimately led him into the insurance and financial services business with PHP. Now a seasoned veteran of more than 13 year…

1
Why this Trump term will be different 47:25

3M ago47:25

47:25

Donald Trump is coming back to the White House. On this episode of Deep Dive, POLITICO’s top Trump-ologist, Meridith McGraw, and Playbook editor Mike DeBonis join host Rachael Bade to discuss how the next Trump presidency will defy our expectations. Included in this discussion: Who will be in Trump’s cabinet; who will lead the GOP on the Hill and c…

1
Samantha Bee and Joanna Coles on ‘The Daily Beast Podcast’ 1:02:25

4M ago1:02:25

1:02:25

Larry is joined by comedian Samantha Bee and chief content officer at The Daily Beast, Joanna Coles, to discuss their latest venture ‘The Daily Beast Podcast’. They begin their conversation by shining a light on how they started the podcast and the interesting way Joanna connects creative luminaries in her industry. They then quickly pivot to an ex…

1
What top election forecasters are predicting for Tuesday 45:21

4M ago45:21

45:21

Top election forecasters Lakshya Jain (Split Ticket) and Logan Phillips (Race to the White House) join Playbook co-author Eugene Daniels to give their key insights and predictions for Tuesday. They discuss how to analyze early voting returns, who the remaining swing voters are, and why polls are more useful than most people give them credit for. St…

1
Ep. 222- Kimberly Davis: Helping The Survivors 1:14:28

4M ago1:14:28

1:14:28

-The guys close out Domestic Violence Awareness Month with a conversation with Kimberly Davis of The Family Place. In a talk about solutions and the aftermath of domestic violence, Davis details how a random girls’ trip got her started on the journey to helping survivors of domestic abuse on multiple levels. The Chicago native explains how the earl…

1
Craig Unger on ‘Den of Spies: Reagan, Carter, and the Secret History of the Treason That Stole the White House’ 1:01:38

4M ago1:01:38

1:01:38

Larry is joined by journalist and writer Craig Unger to discuss his newest book ‘Den of Spies: Reagan, Carter, and the Secret History of the Treason That Stole the White House’, which investigates the secret collusion between the U.S. government and Iran and how it affected the 1980 presidential election. They begin the pod by diving into the histo…

1
Normal Trump vs. Dangerous Trump 40:09

4M ago40:09

40:09

Election Day is less than two weeks away. And Donald Trump has been employing an innovative strategy to keep Democrats’ — and an increasingly large number of Republicans’ — doubts about his fitness for office at bay. The former president has been burnishing his image on a nontraditional media spread of podcasts, golf outings, and shifts working at …

1
Ep. 221- Cydra Branch: Choose You 2:03:23

4M ago2:03:23

2:03:23

The guys continue their focus on domestic violence awareness as they sit down with Cydra Branch. The Ft. Worth native opens up about how some early traumatic childhood experiences helped to set her on a path of trials and tribulations through her teens and early 20's. Now a mom of three kids, the pharmaceutical veteran talks about the multiple wate…

1
Nate Silver on “On the Edge: The Art of Risking Everything” 1:22:07

4M ago1:22:07

1:22:07

Larry weighs in on his recent tour, the newest season of ‘Reasonable Doubt’, and the upcoming presidential election. He’s then joined by writer, statistician, and founder of the site FiveThirtyEight Nate Silver to discuss his newest book ‘On the Edge: The Art of Risking Everything’ (15:27). They begin their conversation by talking about why certain…

1
Why Democrats see 'warning signs' in Pennsylvania 42:59

4M ago42:59

42:59

Trump, Harris, and the vast network of campaigns, Super PACs, and down ballot candidates operating alongside them are now on pace to spend $1 billion before election day in Pennsylvania. For the time being, it is the center of the political universe. On this episode of Deep Dive, Playbook co-author Eugene Daniels is joined by two local experts on t…

1
Ep. 220- Justin Giboney: Politics Are Consequential 44:00

4M ago44:00

44:00

-The guys hop in the virtual lab to talk about politics and the upcoming election with Justin Giboney of the AND Campaign. The Atlanta resident talks about the inspiration for the organization and the role their playing in the modern political space. Giboney breaks down the importance of voting in this current political landscape and what Americans…

1
The 'boys vs. girls' election 48:57

4M ago48:57

48:57

The 2024 election. It’s a contest between Kamala Harris and Donald Trump. But increasingly, it also looks like it’s girls versus boys. Playbook’s Rachael Bade caught up with Sarah Longwell, Executive Director of Republican Voters Against Trump, Publisher of The Bulwark, and Host of "The Focus Group" Podcast, to learn what is driving a record-settin…

1
Yuval Noah Harari on ‘Nexus: A Brief History of Information Networks from the Stone Age to AI’ 1:29:53

4M ago1:29:53

1:29:53

Larry is joined by historian and author Yuval Noah Harari in front of an audience at Live Talks L.A. to discuss his newest book, ‘Nexus: A Brief History of Information Networks From the Stone Age to AI.’ They begin their conversation by talking about the nature of information and how it's been manipulated throughout human history, starting with the…

1
How not to get fooled by “biased polls” this election 42:32

5M ago42:32

42:32

Joining Playbook’s Eugene Daniels on this episode of Deep Dive are two pollsters who know how to find the signal in what has been a very noisy election. John Anzalone aka “Anzo,” was Joe Biden, Hillary Clinton, and Barack Obama’s pollster. And Greg Strimple is a veteran of John McCain, Chris Christie, Rick Perry, and John Cornyn’s campaigns. Togeth…

1
Ep. 219- Kristy Kerns: A Survivor’s Story 1:21:14

5M ago1:21:14

1:21:14

-In observance of National Domestic Violence Month, Cuff and Mo sit down with Kristy Kerns to discuss her harrowing story of surviving multiple abusive relationships. The Georgia native opens up about her first-hand experiences in traumatic relationships and how despite repeating some of the same missteps in choosing a partner, she managed to survi…

1
The “giant opening” Trump has given to Harris | James Carville 39:15

5M ago39:15

39:15

James Carville is one of the oldest and best known political strategists in America. He also is the subject of a new CNN documentary called “Winning is Everything, Stupid.” On this episode of Deep Dive, Carville talks with host Ryan Lizza about his outlook on the election, including why he’s not so sure that it’ll be a close race once the votes are…

1
Abby Phillip on ‘NewsNight with Abby Phillip’ 59:52

5M ago59:52

59:52

Larry is joined by journalist and host of CNN’s ‘NewsNight’, Abby Phillip, and they begin their conversation by discussing Donald Trump and his influence on the news media and the Republican Party. They then pivot to Kamala Harris and shine a light on her meteoric rise to the top of the Democratic ticket and break down the effectiveness of her medi…

1
Inside the mind of Harris' messaging maven 44:21

5M ago44:21

44:21

Brian Fallon, senior communications adviser for Kamala Harris’ presidential campaign, joins Playbook’s Eugene Daniels to discuss the inner workings of the vice president’s campaign, including why her positions on the issues have shifted since 2019, when she’ll start opening up to the press and how her view of Trump differs from Biden’s. Ryan Lizza …

1
Will Packer on ‘Fight Night: The Million Dollar Heist’ 1:18:19

5M ago1:18:19

1:18:19

Larry weighs in on the debate between Donald Trump and Kamala Harris. He’s then joined by producer Will Packer to discuss his new Peacock limited series ‘Fight Night: The Million Dollar Heist’. They begin their conversation by discussing the premise and history behind the project, which leads to a discussion about the art of creating content in tod…

1
The “wall of lava” approaching Kamala Harris’ campaign 56:25

5M ago56:25

56:25

Mike Murphy, the storied GOP strategist and co-host of the popular “Hacks On Tap” podcast, joins Deep Dive host and Playbook co-author Ryan Lizza to discuss Tuesday’s debate and why some very strong winds are still at Trump’s back; how Murphy would tweak Kamala Harris’s message; what might become of the Republican party after Trump and how he, Mike…

1
Ep. 218: Will Harris - Impact Over Income 37:21

5M ago37:21

37:21

-Cuff and Mo have a second conversation with Will Harris of The Hustle Marketing & Design Co. to get caught up on the growth of the company and what it looks like when the hard work you put in starts to bring your vision into a reality. Harris really opens up about the path that led him to starting the company and the multiple sink or swim moments …

1
How to win the Latino vote in 2024 54:37

5M ago54:37

54:37

Everyone knows the Latino vote will be decisive in this presidential election year. But our guest today says most of what you know about Latino voters and how to win them over is wrong. Mike Madrid is a third-generation Mexican-American and one of the country’s leading political strategists when it comes to Latino voters. He was a senior operative …

1
Introducing 'Power Play': How to win a TV election debate 34:28

6M ago34:28

34:28

A special bonus episode from Deep Dive's POLITICO sister podcast, Power Play: With the U.S. presidential debate now confirmed, our Power Play guests explain the tips and tricks that could help Donald Trump or Kamala Harris win their first head-to-head encounter on Sept. 10 — and why there has been a pre-debate row over format and mics. POLITICO’s A…

1
Ep. 217- Cuff & Mo: FOCUS 46:29

6M ago46:29

46:29

FOCUS! -The guys sit down to have a conversation about the concept and actual practice of FOCUS. Mo opens up about what the term means to him and how he has completely cut out any form of distraction while on his professional journey. After Cuff talks about some of the ups and downs he has experienced over the past couple of years, the guys examine…

1
Sophia Cai on the DNC 1:12:48

6M ago1:12:48

1:12:48

Larry weighs in on the state of the presidential race and shares some of dates of his upcoming tour. He’s then joined by Sophia Cai from Axios and they begin their conversation by talking about Kamala Harris’s historic rise to Democratic presidential nominee and the change in party dynamics after Joe Biden dropped out of the race. They then examine…

1
Nancy Pelosi's Democratic survival guide 39:56

6M ago39:56

39:56

Democratic kingmaker Nancy Pelosi has come to be pegged as the chief force behind President Joe Biden’s decision to step down from his reelection campaign — a claim that she refuses to dignify much. While Pelosi no longer wields the Speaker’s gavel, its absence hasn’t done much to stifle her power within the party. She’s not only the first female S…

1
Bernie Sanders’ tough love for the Harris campaign 35:56

6M ago35:56

35:56

Vermont Senator Bernie Sanders joins Playbook co-author and Deep Dive host Ryan Lizza to give his candid thoughts on Kamala Harris’s presidential campaign, including whether he thinks Joe Biden should have stepped aside in the first place; how Democrats can win back young people, minorities, and progressives; as well as where he agrees with Harris’…

1
Langston Kerman on ‘Bad Poetry’ 1:10:52

6M ago1:10:52

1:10:52

Larry is joined by actor, writer, and comedian Langston Kerman to talk about his brand new Netflix stand-up comedy special ‘Bad Poetry’, streaming on Aug. 20th. They begin their conversation by breaking down different types of comedy writing and examining Langston’s process when coming up with themes for a special. This leads to discussions about d…

1
The new fundamentals of the 2024 campaign 50:46

6M ago50:46

50:46

With the Democratic National Convention just days away, Doug Sosnik, a longtime Dem strategist best known for being a top adviser to Bill Clinton, joins the show to help unpack the new fundamentals of the 2024 presidential campaign. Sosnik and Playbook co-author Ryan Lizza discuss: Why the gender gap is getting larger — and how it could impact the …

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