Walgreens' Executive Chair Stefano Pessina Seeks To Strengthen Control With Nearly Double Stake

Earlier this month, Sycamore Partners agreed to acquire Walgreens Boots Alliance Inc WBA for $11.45 per share in cash at closing. Shareholders are also eligible to receive up to $3 in cash per share from the future monetization of Walgreens’ debt and equity interests in VillageMD, which includes the Village Medical, Summit Health and CityMD businesses.

Soon after, Gary Black, managing partner at The Future Fund LLC, said, “I’ve talked before about how this company shouldn’t be public,” adding that the move is driven by its largest shareholder, executive chairman Stefano Pessina, who holds a 16.9% stake.

The Financial Times, citing sources, writes that Stefano Pessina plans to nearly double his stake in the company to about 30% as part of its acquisition.

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The move signals Pessina’s deepening involvement in the company’s future, potentially ahead of a breakup of its various business units.

The FT report added that the transaction will allow Walgreens to restructure the struggling pharmacy giant. Walgreens is currently in a 35-day window to evaluate competing offers.

Pessina’s existing stake is worth approximately $2.1 billion. The deal’s complex financing structure is expected to allow Sycamore to potentially separate Walgreens’ various business units into independent entities, reviving the possibility of selling Boots after previous failed attempts.

Walgreens’ market value once exceeded $100 billion following the 2014 merger of Walgreens and Alliance Boots, a deal orchestrated by Pessina. However, the company’s value has since fallen below $10 billion, facing mounting challenges from online competitors and shifting consumer habits.

Sources indicate that Pessina played a key role in securing the Sycamore deal as he sought a solution to Walgreens’ declining stock price.

In January, Walgreens reported first-quarter sales of $39.46 billion, up 7.5% year over year (+6.9% on constant currency), beating the consensus of $37.28 billion, reflecting sales growth across all segments.

Analysts estimate Walgreens’ second quarter 2025 adjusted EPS of 53 cents, with sales of $37.9 billion. Wall Street forecasts 2025 adjusted EPS of $1.61 and sales of $151.6 billion.

Price Action: WBA stock is down 0.04% at $11.26 at the last check Tuesday.

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