Bruised from last year’s Express Scripts fiasco—analysts estimate that Walgreen’s contract dispute with the giant employee-benefits firm resulted in $4 billion of lost revenue—this former pharmacist needs a big win. Good thing he’s not shy about making big bets. Wasson’s recent deal to buy 45 percent of Alliance Boots, a European pharmacy chain, gives the nation’s largest drug retailer a footprint overseas for the first time, plus a big boost in the high-margin (but uber-competitive) cosmetics market.

Photograph: KUNI TAKAHASHI/CHICAGO TRIBUNE