Walgreens, once a cornerstone of American retail, has faced a dramatic fall from grace.

Earlier this week, the pharmacy giant was sold to private-equity firm Sycamore Partners for just $10 billion – a staggering decline from its nearly $100 billion valuation in 2015. The deal marks the culmination of a decade-long struggle for the Chicago-based chain, taking it off of the stock market after just shy of 100 years.

“Meaningful value creation will take time, focus, and change that is better managed as a private company,” said CEO Tim Wentworth, pointing to Sycamore’s track record of retail turnarounds as a potential lifeline.

Walgreens’ woes are extensive. As as consumers increasingly turned to e-commerce giants like Amazon for everyday essentials, Walgreens struggled to keep pace. Meanwhile, rivals like CVS merged with health insurers, gaining control of the lucrative reimbursement market. Caught on a tightrope, Walgreens failed to find its balance. In Oct. 2024, the company announced plans to close 1,200 stores in an effort to stem its financial losses.

The company’s difficulties were worsened by a series of costly missteps in tech and healthcare. Walgreens invested $140 million in Theranos, a blood-testing startup that promised to revolutionize diagnostics. The partnership aimed to place Theranos clinics in Walgreens stores, but the deal fell apart after the startup’s devices were found to misdiagnose patients, leading to its collapse.

Further complicating the company’s strategy, Walgreens poured $6.2 billion into VillageMD, a network of primary-care clinics, under the leadership of former CEO Rosalind Brewer, previously a Starbucks (SBUX), Sam’s Club (WMT), and Walmart executive. Walgreens burned through more cash when it spent $9 billion to acquire urgent-care centers, including CityMD, in 2022. These moves only deepened the company’s debt without addressing core challenges in its pharmacy business.

Tech innovations also turned into costly headaches. In a high-profile failure, Walgreens spent $200 million attempting to modernize stores by replacing traditional refrigerator doors with digital screens. The experiment flopped, signaling a broader failure to innovate effectively. As cash flow lagged, debt mounted, and shares plummeted, the company’s future grew increasingly uncertain.

In January, Walgreens suspended its 91-year-old quarterly dividend to conserve cash amid rising debt and legal troubles. That same month, the U.S. Justice Department sued the company over millions of questionable opioid prescriptions. In Sept. 2024, Walgreens agreed to pay $106 million to settle false payment claims.

Enter Sycamore Partners, a private-equity firm based in New York that’s known for its work with retail and consumer brands such as Loft and Ann Taylor. Sycamore is expected to either sell off parts of Walgreens, including its Boots pharmacies in the U.K., or work with partners to revive the business. The deal could help refocus Walgreens’ core U.S. retail pharmacy operations while shedding less-profitable assets.

The downfall of Walgreens is emblematic of the challenges facing the U.S. healthcare sector. As competition from Amazon, Walmart, and CVS (CVS) intensifies, even once-dominant pharmacy chains are struggling to stay relevant. The days when Walgreens ruled the wallets of American consumers are long gone.

For the latest news, Facebook, Twitter and Instagram.