WALGREENS

greens Boots’ largest shareholder, with a stake of 16 percent, according to data compiled by Bloomberg.

Walgreens Boots, based in Deerfield, Ill., has a market value of about $55 billion and has $16.8 billion of debt. At that size, a take-private of the company would top the largest leveraged buyout in history. The 2007 sale of Texas utility TXU to Kohlberg Kravis Roberts & Co. and TPG Capital, a deal valued at roughly $45 billion, currently holds the record.

Some of the buyout firms have so far shown reluctance to participate in a deal, the people said. It’s unclear how feasible the transaction would be, and the company could decide against pursuing the idea, the people said.

Representatives for Walgreens Boots and KKR declined to comment.

Shares of Walgreens Boots rose 3.1 percent to $61.52 at 3:38 p.m. in New York trading. Its bonds dropped the most ever.

A buyout would give Walgreens Boots time to adapt to a fast-changing retail landscape, free from the quarter-by-quarter demands of public shareholders.

The company is under pressure from online competitors, including Amazon.com Inc., that have chipped away at front-ofthe-store sales of household and beauty items. While top rival CVS Health Corp. has grown into a vertically integrated health care giant, Walgreens Boots has doubled down on retail, announcing pilot partnerships with retailers including grocer Kroger Co.

It has also announced an ambitious $1.8 billion in annual cost cuts and plans to shutter its instore health clinics.

This wouldn’t be Pessina’s first ambitious private equity deal. The native of Italy previously ran Alliance Boots, which he acquired with KKR in 2007. The transaction came at the height of the buyout boom and underscored the challenges of financing jumbo take-privates, as banks struggled at the time to find buyers for the loans to pay for that deal.

Pessina, 78, took his current role after Walgreen Co. acquired the part of Alliance Boots that it didn’t already own for about $15.3 billion in 2014.

Walgreens Boots is the largest retail pharmacy in the U.S. and Europe, with more than 18,750 stores in 11 countries, according to its most recent annual report. Its wholesale arm has more than 400 distribution centers that deliver to more than 240,000 pharmacies, doctors health centers and hospitals annually. It operates Walgreens and Duane Reade stores in the U.S. and Boots stores in Europe and Asia.

The company had sought to buy rival Rite Aid Corp. But in 2017, the companies scrapped the merger amid regulatory concerns that it would hurt competition in the U.S. drugstore market. Walgreens Boots instead bought roughly 2,000 stores from Rite Aid.