Breaking: Stefano Pessina to near-double stake in Walgreens after Sycamore Partners takeover–reports

March 18, 2025 | by

Another ‘go big or go home’ move by Signor Pessina. The Financial Times reports this afternoon from “people familiar with the matter” that Walgreens Boots Alliance chairman Stefano Pessina will nearly double his 17% stake in Walgreens to 30%, once the take-private sale to Sycamore Partners closes.

Sr. Pessina will be providing cash for the deal by voting 100% of his shares in favor of the transaction, then reinvesting all cash received. According to the FT, his current stake in the listed group is worth as much as $2.1bn which is a handsome chunk of change in this leveraged buyout–and also makes the LBO possible. A sale and take-private also benefits his spouse and business partner Ornella Barra, who heads up the WBA international business.

The $10 billion equity deal could be worth up to $23.7 billion if assets like VillageMD are divested, with the value of net debt, capital leases, and other items are figured in, along with spinoffs, closures, and carveups [TTA 11 Mar]. Those spinoffs are likely to include Boots in the UK, Shields Health Solutions in specialty pharmacy, other international operations, and even Walgreens’ US pharmacy business. Crain’s Chicago Business

The FT in an accompanying article points out that common shareholders are receiving a 63% bump on their current shares’ value. Bondholders who bought in better days, and saw their bonds fall to 65 cents on the dollar, may either have the bonds left outstanding or Sycamore may have to pay it off at par value.

One can only hope for Sr. Pessina that ‘go big or go home’ works out better here than it did with the buys of VillageMD and Summit Health/CityMD.

Editor’s note: expanding on an earlier comment that she offered to Walgreens in reviving a retail model, taking into account how shopping habits have changed even for those of us preferring to shop in person, and reaching out to those who are less able to shop or are far away:

  • Put in or run pharmacies and related health and beauty aids (HBA) sections/aisle in supermarkets, which are already expanding their pharmacy/HBA operations. This could be branded or ‘white label’. One stop shopping. Many supermarkets have their own (Stop & Shop, Publix), but many (e.g. Acme, many Shoprites) don’t have.
  • Create mobile delivery of prescriptions and HBA through mobile vans, pop-ups, and delivery services to homes, senior centers, FQHCs, clinics. Ordering would use voice, text, and online.

Sycamore Partners taking on 83% debt in financing their Walgreens leveraged buyout–some observations

March 13, 2025 | by

An analysis cited in HealthExec of the Walgreens buy from the SEC 8-K filing indicates that Sycamore Partners’ offer is a near-classic leveraged buyout, with Sycamore taking on much more debt than they have assets in their funds. Sycamore is taking on 83% debt, according to the Private Equity Stakeholder Project (PESP) SEC filing analysis. In 2024, PEs took on average 41% in debt.

  • Sycamore’s fund used for the $2.5 billion equity commitment, Sycamore Partners III LP, had at the end of 2024 only $1.29 billion, according to Pitchbook.
  • As this Editor closed yesterday, Sycamore pulled rabbits-out-of-hats to finance the WBA buy. There are at least 15 financial companies involved. The PESP article breaks it down by amount identifying combined investors and lenders. This total is $22.5 billion, with the debt financing alone far higher than the Crain’s Chicago Business report TTA referenced on 4 March.
  • An overview: $5 billion in revolving credit, a a senior secured first-in-last-out term loan facility of $2.5 billion, a $1 billion receivables purchase facility, another senior secured asset-based revolving credit facility of $850 million, another senior secured asset-based revolving credit facility of $2.25 billion, a bridge facility of $2 billion, a preferred equity generating gross proceeds of $1.25 billion, another a senior secured term loan facility in an aggregate principal amount equal to $2,500 million, and a few more billions in bridge loans and loans secured by real property.

To quote the PESP (excerpted from their full statement):

“This leveraged buyout tactic saddles private equity-owned companies with substantial debt, often draining resources that could otherwise be invested in innovation, workforce development, or adapting to market changes.

Instead, companies under private equity ownership must channel much of their revenue toward servicing this debt, leaving them vulnerable to financial distress and bankruptcy.

Sycamore Partners, in particular, has demonstrated problems at the portfolio companies it has owned. Under Sycamore Partners’ ownership, multiple companies, including Belk and Nine West, have filed for bankruptcy.”

Editor’s Note: This Editor shares the PESP’s concerns and adds her own POV.

  • Taking it from the last part, rescuing retail is high-wire-level risk and doesn’t have a lot of successes. Sycamore actually has a few–Staples, Playa Bowls, Ann Taylor, and some others. They also have their share of failures.
  • On LBOs: They happen most when money is scarce and deals resemble hundred-piece jigsaw puzzles. My salad days ‘grad school’ was at a well-remembered airline (right) that was part of the Deregulation Boom. These were largely products of the Golden Age of LBOs in a similarly cash and inflation-strained time, the early 1980s. (I was that little dot on the sidelines.) My next 13 years were spent in a company, Avis, that had previously been acquired and LBO’d so frequently that their only recourse was employee-ownership (ESOP). In both cases, opportunity only went to those willing to take real risks.
  • What happens later is a mixed bag. Avis could not go the distance as an ESOP and to shorten a complicated story, was acquired, then spun off, and back again. New York Air was merged into Continental and out of existence except in fond memory and a few people still with United Airlines or in the industry. Many LBOs, as the PESP notes, end with strapped companies barely hanging on, merged out–or bankrupt. So do many IPOs, particularly the blank-check/SPAC variety. And ESOPs don’t have an easy time either, as later happened with Avis.
  • But the question I have for the PESP: did Walgreens, having been LBO’d a few times itself, sinking under bad decisions, legal actions, and a mountain of debt and general misery, have any alternatives–and what would they be? An ESOP the size of Avis’ is uncommon today, though there are a few hundred annually. Shrinking a retail footprint to profitability is an unlikely strategy, especially for a public company. It looks bad to analysts and shareholders.

If there are alternatives that come up for WBA’s management, the 8-K notes that there is a 35-day ‘go-shop’ period, where WBA is free to seek other buyers. There are also heavy termination fees after this point and allowances for modifications up to 6 March 2026.

Does Sycamore have a path to profitability–even short-term survival–for the pharmacy and base retail operation?There are 310,000 employees across 12,500 retail pharmacy locations in the US, Europe, and Latin America who deserve an answer from Walgreens’ management, beyond the platitudes of press releases.