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Throughout the podcast, Cowherd reflected on his experiences in various locations across the United States. With a history of living in Connecticut, Portland, Las Vegas, and Tampa, he believes that having resided in different regions has enriched his perspective as a broadcaster. Each city contributed uniquely to his understanding of various sports markets and local cultures.
The Chicago Experience
With its storied sports culture, rich history, and vibrant urban life, Cowherd sees Chicago as a fantastic new home. He described it as one of the great American cities with outstanding food, people, and an incredible architectural landscape. Despite mentioning concerns about the effects of COVID-19 on the city, he remains optimistic about its prospects and his new life there.