CVS Health (CVS) rival Walgreen WAG -0.66% (WAG) isn’t going to stop selling cigarettes and other tobacco products anytime soon. Walgreen certainly has myriad financial reasons to keep selling cigarettes. It is faced with cutting costs as it consolidates various functions in its merger with European drugstore giant Alliance Boots.

A billion-dollar forecasting error in Walgreen Co. WAG -1.30% ‘s Medicare-related business has cost the jobs of two top executives and alarmed big investors. At an April board meeting, Chief Financial Officer Wade Miquelon forecast $8.5 billion in fiscal 2016 pharmacy-unit earnings, based partly on contracts to sell drugs under Medicare. Last month, directors got a shock. Mr. Miquelon suddenly cut that forecast by $1.1 billion.

Two exiting Walgreen Co. executives were awarded millions of dollars in parting payments, according to documents filed with the U.S. Securities and Exchange Commission.

Wall Street investors delivered a thumbs down Wednesday to Walgreens’ announcement of a $15.3 billion plan to complete its acquisition of Europe-based Alliance Boots and decision not to pursue potential tax savings by shifting its headquarters overseas.

Walgreen Co. has decided not to relocate its corporate headquarters, people familiar with the matter said, amid complications in pulling off the transaction and a backdrop of heavy political pressure from Washington to end the controversial tax-avoidance move.

Walgreen Co. announced Monday that it has replaced longtime chief financial officer Wade Miquelon with Timothy McLevish, who held the same position at Kraft Foods Group Inc. The move, effective immediately, comes days before the Deerfield-based pharmacy chain prepares to announce its final plans on a projected $16 billion acquisition to complete the takeover of European counterpart Alliance Boots GmbH.

Lawmakers in Washington ratcheted up the pressure on Tuesday on companies seeking tax relief by moving overseas, introducing a bill that would withhold government contracts from companies that undertake so-called inversion deals.

Would Washington politicians rather have a campaign fight than take action to fix the problem of corporations moving overseas for tax reasons? That’s one possibility being raised by a tax-press article that’s getting some attention on Monday.

The Walgreens drugstore chain proudly touts itself as “the pharmacy America trusts.” But many here in this small river town where the founder of the company got his start complain that the drugstore chain is on the precipice of turning its back on the USA.

Protesters gathered at the corner of happy and healthy Thursday to object to plans by the Walgreens Corporation to move its headquarters overseas.

U.S. President Barack Obama will call on Thursday for an end to a corporate loophole that allows companies to avoid federal taxes by shifting their tax domiciles overseas in deals known as “inversions,” White House officials said.

A large US pension adviser has written to US regulators asking them to investigate Illinois-based retailer Walgreens plans to move its tax base from the US to Switzerland as part of its takeover of Alliance Boots.

Even if there’s no way to stop U.S. corporations from shedding their U.S. identities and becoming foreign corporations, there’s no reason they should retain the privileges of U.S. citizenship.

Years ago, I noticed that America’s major drugstore chains tend to utilize the same corporate color scheme. Walgreens, CVS, Rite Aid—all patriotic in red, white, and blue. Even regional chains take their identity cues from Old Glory. But this July 4, American corporations—including one drugstore chain, in one recent example—are using tax loopholes to act in the most unpatriotic of ways.

Mr. Wasson’s actions, however, could soon run counter to his words. The same chief executive who said he was so “proud of our Illinois heritage” is now considering moving the company’s headquarters to Switzerland as part of a merger with Alliance Boots, a European drugstore chain. Why? To lower Walgreen’s tax bill even further.