iHeartMedia, once known as Clear Channel Communications, began in 1972 as a single radio station in San Antonio, Texas, founded by Lowry Mays and Red McCombs. The company rapidly expanded after the Telecommunications Act of 1996 eliminated ownership caps, allowing it to acquire hundreds of radio stations, television outlets, billboards, and live entertainment assets. By the early 2000s, it controlled over 1,300 radio stations globally, becoming the dominant force in American audio and outdoor advertising. In 2006, private equity firms Bain Capital and Thomas H. Lee Partners executed a $26.7 billion leveraged buyout, loading the company with over $20 billion in debt—just months before the 2008 financial crisis. This crippling debt burden led to years of financial strain, culminating in iHeartMedia’s Chapter 11 bankruptcy filing in March 2018. As part of its restructuring, the company shed $10 billion in debt, emerged in May 2019 with $5.75 billion remaining, and separated its outdoor division. Under CEO Bob Pittman, a media veteran known for co-founding MTV, iHeartMedia rebranded and pivoted aggressively toward digital audio, launching iHeartRadio in 2008 and expanding into podcasting through strategic acquisitions like Stuff Media and Triton Digital. By 2024, it became the world’s largest podcast publisher, while maintaining over 850 radio stations and reaching more than 276 million monthly listeners. However, the company continues to face severe financial challenges, including looming debt maturities of $1.8 billion and $800 million due in 2026, sparking concerns of a potential ’Chapter 22’ bankruptcy. The 2020 pandemic exacerbated its struggles, forcing executive pay cuts and widespread employee furloughs—many of which became permanent layoffs, drawing criticism for corporate insensitivity. Despite reporting revenue growth, iHeartMedia posted losses exceeding $1 billion in both 2023 and 2024, highlighting the tension between digital transformation and unsustainable debt. The company’s legacy is marked by industry consolidation that critics say homogenized radio, reduced local programming, and centralized music promotion power. Yet, its adaptation to streaming, podcasting, and live events reflects a broader media shift toward multi-platform audio. iHeartMedia’s story underscores the risks of leveraged buyouts, the fragility of traditional media in digital disruption, and the human cost of corporate restructuring. As it seeks debt extensions and asset sales to survive into 2029, its future remains uncertain—a cautionary tale of ambition, resilience, and the enduring power of sound in a fragmented media world.