It was the deal of a generation. Joe Natale, chief executive officer of Rogers Communications Inc., Canada’s biggest wireless operator, struck a $16 billion agreement in March to take over rival Shaw Communications Inc. The long-anticipated union of two prominent business clans marked the birth of a new national champion. Flying into Calgary one bleak day last winter, Natale met his counterpart in an airport hangar to thrash out the key terms of the union, one that had been coveted for decades by the company’s late founder, Ted Rogers. Risky, debt-laden, yet potentially transformative, it was the kind ...