Greg Wasson recently celebrated his 34th year working for Walgreen Co., including the past five as its president and chief executive.
When he took the reins in February 2009, the Deerfield-based pharmacy chain had a reputation as conservative, stable and risk-averse.
And although the small-town Indiana native has insisted that he doesn't have the stomach to gamble, his tenure has been marked by bold moves and big bets.
With Walgreen poised to complete a $16 billion acquisition to take over the remainder of its European counterpart, Alliance Boots GmbH, Wasson is more than ever in the spotlight, and the glare has been harsh.
Over the past several months, Wall Street analysts and investors have exerted increasing pressure on Wasson and his team to go through with a so-called inversion, in which the company would move its official corporate headquarters to either the United Kingdom or Switzerland to take advantage of a lower corporate tax rate.
That has sparked criticism from politicians and activists who fear that he will uproot Walgreen's corporate headquarters from Illinois to a European tax haven. Illinois Sen. Dick Durbin has introduced legislation to help curb such moves.
On top of that, some stock analysts have questioned whether Wasson, who started with the company as a pharmacist, and his management team have the chops to lead a giant multinational company once the Boots deal closes.
In an interview Thursday, Wasson was characteristically optimistic, defending the company's performance since the deal to acquire Boots was announced in 2012. He said he fully intends to remain CEO should Walgreen opt to go forward with its plan to buy the remaining 55 percent of Boots in the coming months.
"This is obviously the board's decision, but I'm excited with what we're about to do," Wasson said. "If our board does take Step 2 … I'm excited to see the company through. I fully expect to, and I'm excited to lead the company."
Wasson on Thursday would not reveal the company's plans, but he said his duty is to "optimize shareholder value and what's in the best interest of the company long term."
Walgreen, which in late June withdrew its profit goals for its 2016 fiscal year because of unforeseen pressure in its pharmacy operations and a lack of clarity on the final structure it would take after its acquisition of Boots, plans to update investors in a special call in late July or early August.
In that call, executives are expected to detail the final timing and structure of the transaction, as well as name the combined management team and determine where the company will be based.
"There are a lot of investors out there that are suggesting, and want us to at least consider an inversion. Frankly, it's my fiduciary responsibility to explore all structures and all options and weigh the risk-reward scenarios with all of the above, as we are," Wasson said.
In order for Walgreen to complete the purchase of Boots, it must file a proxy and hold a shareholder vote, steps that are expected this fall.
Under terms of the initial purchase agreement, the window for Walgreen to complete the transaction is slated to begin Feb. 5 and extend six months.
It also allows Walgreen and Boots to alter those dates, and analysts have said the two firms may seek to move the transaction into 2014 to avoid any potential changes to U.S. tax regulations that may take effect in 2015.
Some analysts have taken note of Wasson's renewed willingness to consider major changes in the way it approaches the Boots takeover.
"We have been highly encouraged by the recent statements of Walgreen's management that acknowledge the need to address the company's cost structure and indicating that they are examining opportunities to optimize capital structure and maximize tax efficiencies," Barclays analyst Meredith Adler wrote in recent report widely cited throughout the investment community.
That report put into writing what other analysts had been saying for months: Shareholders are growing increasingly restless with the management team and "pressure is mounting to bring in a new team" led by Stefano Pessina, executive chairman of Alliance Boots.
Although Walgreen stock trades for about $74 a share, near an all-time high, some investors have complained that the company hasn't done enough to rein in costs like its largest competitor, CVS Caremark Corp.
They also were dismayed by the way Walgreen management handled a protracted contract spat with Express Scripts Holding Co., a pharmacy benefit manager that once sent 88 million prescriptions a year through Walgreens stores.
Walgreen spent more than nine months outside of network for customers of Express Scripts, which administers prescription drug benefit programs for health insurers, employers and other groups. Analysts said Walgreen may never get some of those customers back, a misstep that investors viewed as an unforced error.
Amid that fiasco, Walgreen agreed to the deal to acquire a 45 percent stake of Switzerland-based Alliance Boots for $6.7 billion.
Investors and analysts questioned whether Walgreen management had the wherewithal and savvy to get good value out of the deal, in part because it was up against Pessina, an Italian billionaire who has a reputation in Europe akin to Warren Buffett in the U.S.
But Wasson said he and Pessina, who is now Walgreen's largest shareholder, have forged a "great relationship," and are aligned on how to best structure the combination of the two companies for mutual benefit.
"I'm feeling good," Wasson said. "We are absolutely on our way to become the leading global pharmacy, health and well-being enterprise that Stefano and I had identified when we put this together back in 2012."