In this episode, hosts Nate and Mike smoke the Peloto Cubano cigar, sharing candid impressions of its inconsistent quality and unusual labeling. Nate recounts a recent trip to Chicago to meet longtime friend Simcha and experience a traditional Jewish Shabbos (Sabbath) with him and a guest named Thomas, an incoming convert to Judaism. They discuss the cultural and religious practices observed during Shabbos, including the unique restrictions and rituals around lighting fires, using electronics, and kosher food traditions.

Nate also explores Chicago’s rich architectural history, taking a detailed tour of the historic Rookery Building and reflecting on the city’s connection to the 1894 World’s Fair and famous figures like Daniel Burnham and Frank Lloyd Wright. The episode touches on philosophical debates about free will that arose during the visit, as well as the myth and cultural significance surrounding Noah’s Ark.

Additionally, Nate shares humorous stories about the challenges of finding a budget-friendly cigar called "Level" at Binny’s liquor and cigar store in Chicago, as well as discussions about regional drinking cultures and liquor laws in the Midwest versus other parts of the U.S.

The episode blends cigar reviews, personal travel anecdotes, cultural exploration, and philosophical musings, all delivered with a casual, conversational tone. Listeners get a mix of cigar insights, experiences with Jewish traditions, and reflections on friendship and discovery.

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