Alyssa Mastromonaco, who served on the Obama transition team, and Caroline Reston, a podcast producer, delve into the fascinating world of presidential transitions. They share behind-the-scenes stories from the 2008 Obama administration, highlighting the chaotic shift from campaign to governance. The duo discusses the importance of communication during transitions, the absurdities of cabinet application processes, and the lessons learned from past administrations. Their playful banter adds a humorous touch to the serious nature of political handovers.

Alyssa Mastromonaco, former Deputy Chief of Staff to Vice President Joe Biden, engages in a riveting dialogue with Nancy Pelosi. They address Pelosi's experience as one of Trump’s 'enemies within' and the anxieties keeping her up at night. The conversation shifts to the drastically contrasting campaign messages, with Kamala Harris advocating for unity and reproductive rights while Trump stirs up division. They also dissect the critical impact of recent rallies on voter sentiments, especially focusing on essential issues like economic policy in Puerto Rico.

In this insightful discussion, Alyssa Mastromonaco, former White House deputy chief of staff and COO of Vice Media, opens up about the pressure of high-stakes leadership and managing anxiety. She reflects on the need for breaks to recognize mental health symptoms that often go unnoticed in a relentless work culture. Alyssa shares her personal journey through career transitions, emphasizing the importance of redefining identity outside of work. Her candid embrace of mental health transparency highlights how openness can create supportive workplace environments.

Alyssa Mastromonaco joins Jon as guest host, and Strict Scrutiny’s Leah Litman breaks down the strength of the legal case behind Trump’s third indictment. Trump’s Republican opponents react to the new felony charges. A New York Times poll has Trump tied with Joe Biden. And later, Halle Kiefer joins for another round of Well, Well, Well, Looks Like Everyone’s A Fucking Lawyer All Of A Sudden. For a closed-captioned version of this episode, click here. For a transcript of this episode, please email transcripts@crooked.com and include the name of the podcast.

Former White House Deputy Chief of Staff Alyssa Mastromonaco, along with hosts, dissect Trump's immunity argument at the Supreme Court, Idaho's abortion ban, and Harvey Weinstein's overturned conviction. They delve into Biden administration's moves, TikTok ban, and VP selection secrets.

Former Obama campaign members Jon Favreau, Robert Gibbs, Reggie Love, and Alyssa Mastromonaco share memories, reflect on the historic nature of the 2008 election, and discuss topics such as writing Obama's victory speech, the weight of the financial crisis, the significance of Obama's presidency, and the power of hope in his speeches.

Guest host Alyssa Mastromonaco joins Jon, Jon, Tommy, and Dan live from Cleveland, Ohio. They discuss the political implications of the war in Gaza, the shrinking Republican primary field, and the upcoming Ohio election that will decide the fate of abortion access. They also cover topics such as Magic Spoon cereal, therapy benefits, and the rise of Mike Johnson. The speakers delve into legal proceedings, the fight for abortion rights in Ohio, and marijuana legalization. They wrap up by expressing gratitude and promoting their YouTube channel and Potsubscription community.

Friend of the pod Alyssa Mastromonaco, former Deputy Chief of Staff under Obama, talks about what to expect from the Biden-Trump debate. Also, Supreme Court accidentally hints at allowing emergency abortions in Idaho, Midwest faces dangerous flooding, and Alex Morgan left off US Women's National Team's Olympic roster.

Friend of the Pod Alyssa Mastromonaco and Hawaii Senator Mazie Hirono join Dan to discuss the latest impeachment madness, the potential destruction of government, Trump's claims of popularity, recovery efforts in Maui, and listener questions.

Alyssa Mastromonaco discusses leaving the White House after sleep deprivation, binge-watching HGTV, and her newfound love for jam making. They also touch on the challenges of transitioning from a high-stakes environment to a more relaxed one and the importance of being politically active in grassroots elections.