The Jamie Weinstein Show

Brian Stelter is CNN's media critic-in-chief.

In the latest episode of The Jamie Weinstein Show, CNN's senior media correspondent and host of CNN's "Reliable Sources" discusses covering the media in the Age of Trump, his thoughts on media bias, his relationship with famous media figures, his influences, and much more. Show Roadmap:

• What has surprised Stelter about the Trump presidency.
• On his interactions with Trump.
• On how the media have covered Trump — and whether he thinks it has erred at all.
• Does the media try to keep us in a constant state of outrage?
• Does media political bias infect the news?
• On the pro-Trump voices at CNN.
• Stelter on his favorite non-CNN cable news shows.
• On how Trump changed presidential politics — and why he thinks Oprah 2020 could happen.
• Can he imagine a successful Trump presidency?
• On Jeff Zucker, Tucker Carlson, Alex Jones, Sean Hannity, Roger Ailes, Jared Kushner, and Matt Drudge.
• On his career and influences.

Boris Epshteyn is no stranger to controversy. In the latest episode of The Jamie Weinstein Show, the chief political analyst for the Sinclair Broadcast Group and former Trump administration official opens up about the rise of Trump, why his critics are wrong to call him a Trump administration propagandist, whether he signed a non-disclosure/non-disparagement agreement while working for the Trump campaign, the Russian collusion investigation, his influences, and much more. Roadmap:

• What has surprised Epshteyn about the Trump administration's first year and a half.
• Why Epshteyn thinks Trump won the Republican primary.
• What Epshteyn makes of the state of the media.
• Epshteyn defends himself and the Sinclair Broadcast Group against charges it is pro-Trump propaganda.
• On whether Epshteyn signed a non-dislosure/non-disparagement agreement with Trump and whether that should matter in his new media role.
• On whether he disagrees with Trump on any issue, from the debt to North Korea.
• What Epshteyn makes of the Russia collusion investigation.
• On Eric Trump, Paul Manafort, Matt Drudge, Alex Jones and Steve Bannon.
• On his career and influences.

Ezra Klein has a had a meteoric rise in journalism. In the latest episode of The Jamie Weinstein Show, the founder of Vox opens up about the rise of Trump, the Russia investigation, the media, and much more.

Show Roadmap:

• What has surprised Ezra about the Trump presidency.
• Why Ezra thinks Trump won the Republican Primary — and the general election.
• Whether Ezra is more concerned about President Trump than a President Pence.
• What Ezra makes of the collusion investigation.
• Ezra on the nomination of Brett Kavanaugh and the state of Supreme Court fights.
• Why Ezra initially supported the Iraq war.
• What Ezra makes of Never Trumper-ism.
• On whether Vox is a liberal publication.
• Closing Questions.

Larry O'Connor is a professional talker.

In the latest episode of The Jamie Weinstein Show, the host of WMAL's The Larry O'Connor Show opens up on what's surprised him about Trump's presidency, what he thinks should happen if the alleged racist Apprentice outtake tape exists, his influences, and much, much more. Show Roadmap:

• What's surprised O'Connor about the Trump presidency.
• Who O'Connor supported in 2016 GOP presidential primary and why he thinks Trump won.
• How important is the Supreme Court in presidential politics.
• O'Connor's take on the Trump-Putin summit.
• Should character matter in presidential politics?
• What O'Connor thinks of the Mueller investigation.
• How O'Connor thinks the media has covered Trump.
• Did O'Connor lose any friends over the 2016 election?
• On Matt Drudge, Stephen Miller and Steve Bannon.
• On his career and influences.

Matt Lewis is a conservative in a Washington no longer welcoming to conservatives.

In the latest episode of The Jamie Weinstein Show, The Daily Beast columnist and CNN contributor Matt Lewis returns to discuss what it would take him to vote for Trump in 2020, the state of Never Trump, the negative incentives that drive media coverage, and much more.

Show Roadmap:

• What has surprised him since Trump took office.
• What it would take for Lewis to vote for Trump in 2020.
• How the GOP became the "Blame America First" party.
• The state of Never Trump.
• How the left has handled Trump's presidency.
• On the state of the media and how podcasts are a bright spot in a sea of darkness.
• Whether Lewis feels the Collusion narrative is more plausible after Helsinki.
• On Matt Drudge, Sarah Palin and Steve Bannon.
• When Matt Lewis had dinner with Alex Jones.
• On his career and influences.

Not too long after moving to the United States from Australia, Jonathan Swan has become one of the best-sourced White House reporters in the country.

In this latest episode of The Jamie Weinstein Show, Jonathan Swan, the star of Axios, opens up on what has surprised him about the Trump presidency, who holds influence in Trump world, how he achieved his rapid success, and much more. Show Roadmap:

• What has surprised him since Trump took office?
• How Trump sees the world.
• On who, if anyone, Trump listens to for advice.
• On the role of Steve Bannon, Ivanka Trump and Roger Stone within Trump world.
• On whether anyone in the White House thinks Putin may have something on Trump.
• On whether Republicans in Congress will ever revolt.
• Is there any candidate Trump fears running against in 2020?
• On Matt Drudge, Anthony Scaramucci, Don Trump Jr., Sean Hannity and Elliott Broidy.
• How Swan became one of the best sourced White House correspondents.
• On his influences.

If you don't know who Sean Spicer is, you are probably not reading this.

In the latest episode of The Jamie Weinstein Show, the former White House press secretary for President Trump and author of the new book "The Briefing" opens up on his time in the White House, civility in the Age of Trump, the state of the media, and much more. Show Roadmap:

• What's surprised Spicer about Trump's first 18 months.
• What Spicer has learned from his personal interactions with Trump.
• Spicer on what he thought when Trump first entered the GOP primary and why Trump won.
• Did any of Trump's rhetoric on the campaign trail concern Spicer?
• On the importance of honesty in a U.S. president.
• How Spicer handled Trump's tweets as press secretary.
• On the Helsinki summit and Trump's response.
• On Never Trumpers and whether Spicer lost friends because of the the 2016 election.
• How Hollywood treated Spicer at the Emmys.
• On Anthony Scaramucci, Matt Drudge, Steve Bannon and Alex Jones.
• How to become the next Sean Spicer and whether Spicer would run for office.
• On his influences.

Charlie Kirk isn't wasting time. In the latest episode of The Jamie Weinstein Show, the 24-year-old head of the conservative activist organization Turning Point USA opens up about his relationship with Donald Trump, why he is an unabashed supporter of Trumpism, his meeting with Kanye West, his influences, and so much more. Show Roadmap

• Kirk on Trump's first 500 Days
• What Kirk has learned about Trump from his personal interactions with him
• How Kirk defines his conservatism
• Kirk defends criticism of his support of Trump
• On whether he is too quick to praise Trump's North Korean policy as a success
• Is Kirk's outrage on Twitter manufactured or genuine?
• How Kirk met Kanye
• On Confederate Statues, Russia Collusion and the 2017 French Presidential Election
• Name Association: On Donald Trump Jr., Alex Jones and Steve Bannon
• On his career and influences

Few Democrats are as plugged into the Democratic political scene as Neera Tanden.

In the latest episode of The Jamie Weinstein Show, the president of the Center for American Progress, who was reported to be in line for a big White House gig if Hillary Clinton won the 2016 election, opens up about the Trump administration, the internal battles within the Democratic Party, re-evaluating Ted Kennedy and Bill Clinton in the age of #MeToo, and much more.

Show Roadmap

• Evaluating the Trump presidency
• What Tanden thought when Trump entered the 2016 presidential race
• Whether the Democratic Party deserves any blame for Trump's rise
• On whether "the Resistance" should ever work with the White House
• On whether she believes Trump should be impeached
• On the Democrats in 2020 and whether she thinks Trump can win re-election
• On Tom Steyer, Ivanka Trump, Matt Drudge and Steve Bannon
• On her career and influences

Few conservatives are more revered than Thomas Sowell. In the latest episode of The Jamie Weinstein Show, the famed economist and iconoclast opens up about his new book, 'Discrimination and Disparities,' outlines his pessimism about America's future, names his influences, and much more. Show Roadmap– On his new book, "Discrimination and Disparities" – What Sowell makes of Trump administration one year in

– Who is more responsible for the low unemployment rate: Obama or Trump? – Why Sowell is pessimistic about America's future – Could Sowell fix America if he were dictator for a day? – How Sowell almost became a professional baseball player – Why Sowell turned down offer to become the Secretary of Education – On his influences