Ross Barkan is an award-winning journalist, novelist, and essayist based in New York City. He is a columnist for New York Magazine, a contributing writer at the New York Times Magazine, and the editor-in-chief of the Metropolitan Review. A Queens Tribune veteran who came up covering local politics and city streets, Barkan brings deep reporting roots to his work across both fiction and nonfiction — including his latest novel, Colossus.

On this episode, Kevin and Ross discuss the lost art of the big city newspaper columnist, whether great writing and bold opinions can survive in the digital age, the complicated relationship between Donald Trump and the New York media, and what it takes for young journalists to make their mark today.

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Ed Madison, PhD, is a journalist, professor at the University of Oregon, and Executive Director of the Journalistic Learning Initiative, a nonprofit bringing journalism education to students in 18 states. He created a suite of AI-powered writing coaches named after legendary journalists — including one named Jimmy Breslin — built to help young writers develop their skills without doing the work for them.

In this episode, Kevin and Ed discuss how a dead man ended up with a new job, whether AI can ever truly capture the voice and soul behind great writing, and what the future of journalism means for the next generation.

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James Rosselli is a rising sports broadcaster and student at High Point University who has quickly gained attention for his energetic play-by-play style and viral on-air moments. Inspired by a lifelong love of sports and early experience in stand-up comedy, Rosselli has developed a distinctive voice that blends preparation, humor, and storytelling. Still early in his career, he is already building momentum with national exposure and ambitions to reach the highest levels of sports media.

On this episode, Kevin and James discuss his path into sports broadcasting, the craft of calling a game and preparing like a pro, handling pressure and viral attention at a young age, and the evolving future of sports media, including NIL and the business of college athletics.

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Billy Stern is a young entrepreneur and publisher who founded The Ditch Weekly, a print newspaper based in Montauk, New York. While still in high school, Stern built a team of student reporters and launched the paper to cover local stories, community events, and life in the Hamptons. The project quickly gained attention for reviving local print journalism and even drew coverage from The New York Times.

On this episode, Kevin and Billy discuss why he decided to start a print newspaper at a time when many say print is dying, the challenges of running a newsroom with a team of student reporters, how local journalism strengthens communities, and why young people should take risks and build something of their own.

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Victoria Gotti is a bestselling author, columnist, and television personality who built a writing career while growing up in one of New York’s most widely known families. The daughter of John Gotti, she became a novelist and a prominent gossip columnist at the New York Post, publishing several books and appearing frequently in television and media. Despite the intense public scrutiny surrounding her family name, Gotti established herself as a writer with her own voice and perspective.

On this episode, Kevin and Victoria discuss her path into writing and journalism, the challenges of building a media career while her family was constantly in the public spotlight, the ethics and realities of gossip reporting, and her personal memories of her father and life behind one of New York’s most talked-about families.

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Dan Barry is an award-winning journalist, author, and longtime columnist for The New York Times. A Pulitzer Prize–winning reporter and recipient of the Mike Berger Award for narrative journalism, Barry is known for his deeply human storytelling and his acclaimed “This Land” columns that explore the people and character of America. He is also the author of several books, including “Bottom of the 33rd: Hope, Redemption, and Baseball’s Longest Game” and “The Boys in the Bunkhouse: Servitude and Salvation in the Heartland.”

On this episode, Kevin and Dan discuss the legacy and influence of Jimmy Breslin, the discipline and grind behind great newspaper writing, the craft of finding stories others miss, and the humanity and responsibility at the heart of journalism.

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Carl Hiaasen is a bestselling novelist and longtime Miami Herald columnist known for his sharp satire, environmental advocacy, and fearless political commentary. Over a career spanning more than three decades in newspapers, Hiaasen built a reputation for channeling outrage into incisive columns while also crafting wildly popular Florida-set novels filled with eccentric characters and biting humor.

On this episode, Kevin and Carl discuss the role of anger and outrage in great column writing, the changing culture of modern journalism, press freedom in the Trump era, and how fiction can sometimes reveal deeper truths than the daily news.

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Mitch Albom is a bestselling author and longtime columnist for the Detroit Free Press, best known for Tuesdays with Morrie, which has sold more than 40 million copies worldwide. Albom has built a career that bridges sports journalism, deeply human storytelling, and philanthropic work. Known for his emotional clarity and moral voice, he remains committed to newspaper writing while continuing to publish bestselling books and lead charitable efforts in Detroit and beyond.

On this episode, Kevin and Mitch discuss the art of powerful storytelling, lessons from sports journalism and covering the “loser’s locker room,” the state of modern media and press credibility, and why honesty and humanity still matter in writing—and in public life.

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