Affiliated

"Affiliated's investment eventually reached $85 million, and the payoff it yielded staggered the Jordan and Taylor families. Within seven years, the investment's value hit $2 billion—more than the value of the Globe itself. The investment illustrated another recurring theme of the McCaw saga: Big players that do business with McCaw habitually underestimate—often drastically—his cleverness and ambition. "At the time, they thought they were just making a peekaboo investment to buy part of the company and buy the rest later," McCaw later said. "[But] our intentions were to buy them." As it happens, he never did—but not because he couldn't afford it."

"McCaw's goal, as always, was to preserve his independence, flexi- bility, and control. Although he had qualified for the MCI deal on the basis of Affiliated's balance sheet, McCaw ultimately decided to go with a different form of financing, perhaps to show a measure of indepen- dence from his Boston associates. He went with junk bonds, a relatively new form of corporate IOUs at high interest rates, recently popularized by an already legendary trader at Drexel Burnham Lambert named Michael Milken."