In August 2014, Walgreens purchased the remaining 55% of Alliance Boots. On September 10, 2013, Walgreens announced it had acquired Kerr Drug. In 2012, Walgreens announced that it would continue to participate in Express Scripts. Groups sending letters were National Hispanic Christian Leadership Conference, the Congress of Racial Equality, Hispanic Leadership Fund and others. A coalition of minority groups, led by Al Sharpton's National Action Network, sent letters urging CEO Gregory Wasson to reconsider. In 2011 Walgreens announced it would end its relationship with Express Scripts, a prescription benefits manager.

That year, Walgreens acquired Mid-South drugstore chain operating under the USA Drug, Super D Drug, May's Drug, Med-X, and Drug Warehouse banners. On June 19, 2012, Walgreens paid $6.7 billion for a 45% interest in Alliance Boots. In March 2011, Walgreens acquired for $409 million. In 2010, Walgreens acquired New York City-area chain Duane Reade for $1.075 billion, including debt, and continued to use the Duane Reade name on some stores in the New York City metropolitan area. On January 26, 2009, Gregory Wasson was named CEO effective February 1, 2009. On October 10, 2008, Rein abruptly quit as CEO and was replaced by Alan G. That year, Walgreens acquired the Happy Harry's chain in Delaware, Pennsylvania, Maryland, and New Jersey. On July 12, 2006, David Bernauer stepped down as CEO of Walgreens and was replaced by company president Jeff Rein, who was later named chief executive officer and chairman of the board. Walgreen was made a vice-president in 1995 and promoted to senior vice president of store operations in 2006.

In 1986, Walgreens acquired the MediMart chain from Stop & Shop. in 1988, and by 1991 the chain was out of business. Walgreens sold most of these to Marriott Corp. In the 1980s Walgreens owned and operated a chain of casual family restaurants/ pancake houses called Wag's. The Walgreen family was not involved in senior management of the company for a short time after Walgreen III retired. The company also created larger-sized Walgreens Superstores and purchased the Globe Discount City chain of big-box stores from United Mercantile, Inc. Walgreen III took over after Walgreen Jr.'s retirement in the early 1950s and modernized the company by switching to barcode scanning. In 1946, Walgreens purchased Sanborns, one of Mexico's largest pharmacy and department store chains, from Frank Sanborn (Walgreens sold Sanborns to Grupo Carso in 1982). years were relatively prosperous but lacked the massive expansion seen in the early part of the century. took over the chain until his retirement. After Walgreen died in 1939, his son Charles R. By 1934, Walgreens was operating 601 stores in 30 states. The stock market crash in October 1929 and subsequent Great Depression did not greatly affect the company. This expansion partly was attributed to selling prescribed alcohol, mainly whiskey, which Walgreen often stocked under the counter, as accounted in Daniel Okrent's Last Call: The Rise and Fall of Prohibition. Walgreens had also expanded by then into Minnesota, Missouri, and Wisconsin. In the mid-1920s, there were 44 stores with annual sales of $1,200,000 combined. The next year, Walgreens began opening stores away from residential areas. In 1922, the company introduced a malted milkshake, which led to its establishing ice cream manufacturing plants.

Although alcohol was illegal, Walgreens sold prescription whiskey.

As a result of alcohol prohibition, the 1920s were a successful time for Walgreens. By 1919, there were 20 stores in the chain. It opened its fifth in 1915 and four more in 1916. By 1913, Walgreens had grown to four stores on Chicago's South Side. Walgreens began in 1901, with a small food front store on the corner of Bowen and Cottage Grove Avenues in Chicago, owned by Dixon, Illinois native Charles R. Early 'Walgreen Drugs' sign still in use in San Antonio, Texas

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