Walgreens Boots Alliance, a nearly century-old publicly traded company, is going private in a deal valued at up to $23.7 billion. The move comes after a challenging period that saw its market cap plummet from $100 billion a decade ago to just $9.5 billion, with over 10% of its stores shuttered. Private equity firm Sycamore Partners will pay $11.45 per share in cash, potentially reaching $23.7 billion including debt and future payouts. The transaction is expected to close in Q4 2025.

Walgreens, which went public in 1927 after opening its 100th store, has struggled alongside rivals CVS and Rite Aid. Declining prescription reimbursements, competition from Amazon, and pressure from larger retailers like Target have eroded profits. Unlike CVS, which acquired insurer Aetna, Walgreens lacked a strategic payer alignment, instead investing heavily in clinic chain VillageMD. This required significant spending on real estate and technology without delivering scale to negotiate with insurers.

The company’s shares have shed nearly 80% of their value over five years, though they recently rose amid privatization talks. Last October, Walgreens announced plans to close 1,200 of its 8,500 U.S. locations by 2027—up from 300 closures planned in June 2024—targeting unprofitable stores. CEO Tim Wentworth called the privatization a chance to execute a turnaround “better managed as a private company,” with Sycamore’s retail expertise aiding the effort.

Sycamore may sell off UK-based Boots to maximize returns, while Stefano Pessina, Walgreens’ executive chairman and 17% stakeholder, will reinvest his share. Analysts see this as a long-term play to extract value, though growth remains challenging across Walgreens’ pharmacy, healthcare, and retail segments. The deal ends a storied public run for Walgreens, which acquired Duane Reade in 2010 and Alliance Boots in 2014, but now faces a complex path forward under private ownership.