POLITICO Playbook’s Anna Palmer and Jake Sherman - Co-Authors of "The Hill to Die On"

Playbook Evolution and Market Position

• Jake Stewart inherited Playbook three years ago, inheriting a decade-old product originally designed for Blackberry scrolling that required modernization for iPhone consumption.
• The newsletter has been updated to include images and color while maintaining its core function as an easily digestible "Cliff Notes" version of Washington news.
• Frequency has increased from a single daily edition to twice-daily updates five days a week to accommodate a faster news cycle where significant stories emerge before noon.
• Politico and Playbook maintain a strategic focus on being a "village newsletter" for the Washington insider set (D.C., N.Y., L.A., S.F.) rather than attempting to broaden their appeal to general political tourists.
• The firm explicitly rejects the strategy of changing its core product to attract more readers, instead emphasizing that media outlets must be "the ultimate insider newsletter" rather than trying to do everything.

"The Hill to Die On" and Congressional Dynamics

• The book "The Hill to Die On" covers the period from Election Day 2016 through the government shutdown in February 2020, focusing on the first two years of the Trump presidency.
• Primary subjects of the book include Paul Ryan, Nancy Pelosi, Mitch McConnell, and the Freedom Caucus, with the authors conducting interviews over a two-year span.
• Paul Ryan, despite personally opposing Trump and disinviting him from the Access Hollywood event, chose to stay in Congress due to a religious sense of duty and a desire to present a "normal" figure to the American public.
• Ryan's decision to make the repeal of the Affordable Care Act his personal political project led to a loss of credibility with the President after the failure of the initiative.
• Ryan's chart-based pitch to Trump regarding healthcare, intended to create budgetary space for tax reform, failed because Republicans lacked a concrete plan for the complex healthcare topic.
• The failure of the healthcare repeal created the political space necessary for the passage of the Tax Cuts and Jobs Act, which succeeded partly because Trump stepped back and allowed Congress to handle details.
• Mitch McConnell successfully navigated the Trump presidency by prioritizing winning over ideology, often avoiding public commentary to maintain private influence with the President.
• McConnell's approval numbers doubled during the Brett Kavanaugh confirmation process, leading him to view the era as a personal "rock star" moment despite earlier unease regarding Trump.
• The Trump administration's relationship with the Freedom Caucus (specifically Mark Meadows and Jim Jordan) is driven by conservative leaders using cable television, particularly daytime TV, as a primary tool to communicate directly with and influence the President.
• Jim Jordan's strategy of appearing on daytime television daily proved effective after Trump noted a previous CNN appearance where Jordan "kicked Cuomo's butt."

2020 Election Landscape and Media Strategy

• Media outlets are adjusting coverage strategies following the 2016 election by increasing the number of reporters embedded in Rust Belt states like Wisconsin and Ohio to better understand non-elite constituencies.
• Polling failures in 2016 are attributed to a focus on the wrong metrics rather than a total collapse of polling data, with states like Pennsylvania misclassified as solidly Clinton territory.
• The current Democratic field features nearly 20 candidates, with no clear frontrunner other than Bernie Sanders, who holds an estimated 65%+ probability of securing the nomination based on polling and fundraising.
• Joe Biden remains undecided as of the April 12th discussion, consulting with his family and refraining from fundraising or self-definition in a race where 18 other candidates have already raised $18 million hauls.
• Voters appear to favor non-establishment candidates with gubernatorial or mayoral experience, rejecting traditional Washington insiders in favor of outsiders who can promise to fix a "broken" system.
• The influx of Democratic women into elected office is shifting Washington culture toward more authentic self-presentation and attempting to address structural barriers such as family-friendly voting schedules and smaller fundraising networks.
• The administration's use of Twitter and media manipulation has significantly shortened the news cycle, desensitizing the public and media to scandals that would previously have dominated headlines for weeks or months.
• The authors predict that little substantive legislative progress will occur before 2020, as the Trump presidency's constant media noise leaves little "oxygen" for positive governance or bipartisan cooperation.