Matt Trump takes listeners on a deeply personal and historical journey through Portland, once a vibrant hub of music, creativity, and culture, now a city overrun by chaos and ideological decay. Drawing on his own experiences from the 80s, 90s, and 2000s, he reflects on how Portland’s charm and high-functioning community slowly gave way to decadence, slacker culture, and ultimately a city haunted by dark energy. From the glory days of jazz clubs and Restaurant Week to the haunting spectacle of homelessness and lawlessness, Matt examines how Portland became a symbol of the left’s unchecked insanity. Along the way, he dives into history, art, and even his own complicity in the city’s trajectory, weaving a narrative equal parts memoir, cultural critique, and elegy.