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It was Dostoyevsky who observed that "money is coined liberty." Well, Allen was now free. After deploying a fail-safe strategy to gradually cash out his ever-burgeoning Microsoft stock, he accumulated the world's biggest toy collection. His heroic spending binge encompassed cars and yachts and so much fine art that trade magazines were calling Allen one of the world's top-spending collectors. He'd always thought World War II fighter planes were cool, so he bought a bunch of those. A lifelong music fan, he began amassing the world's largest collection of rock and roll memorabilia: Original lyric sheets. Costumes. Guitars. Particularly fond of another Seattle native, Jimi Hendrix, Allen paid an undisclosed fortune for the Stratocaster the rock star played at Woodstock.
He also bought a sports team. Though Allen had never been much of an athlete, basketball had always fed something in him. He spoke to friends about the "poetry of a slam dunk" and impressed them with his knowledge of the NBA. He first tried to purchase the Sonics, but when the team's owners declined, Allen ventured 170 miles south on I-5 to Portland. Few people even knew the Blazers were for sale, but in 1988 Allen snapped them up for $70 million.
The Portland community was initially skeptical of this reticent high-tech tycoon, this interloper from the rival kingdom to the north. But the citizenry quickly warmed to Allen. In a precinct that prides itself on its lack of pretentiousness, there was something undeniably cool about an owner who wore unfashionable clothes and a beard that was a long weekend away from ZZ Top length. Here was a man who would unabashedly cheer courtside but then, after the game, quietly repair—sometimes with his mom in tow—to Powell's World of Books and cruise the science fiction shelves. Keep Portland weird, the slogan goes. The Blazers' owner did his part. Never accused of being arrogant or overbearing or unreasonable, he was simply ... idiosyncratic. "The way he carried himself, you'd never know he owned the team," says Mark Bryant, a Blazer from 1988 to '95. "People in Portland relate to that."
In a one-team town, residents also related to Allen's passion for the Blazers. Fans noticed how often he flew down from Seattle to attend games. Allen was never particularly opinionated, but he called and e-mailed his executives to pepper them with questions. "We'd see that Microsoft would drop four points and think, Paul must have lost millions today, bet he's going crazy," recalls Brad Greenberg, a Blazers front-office executive from 1989 to '94. "Then the phone would ring, and it would be Paul calling about some second-round prospect from Dayton."
In the mid-'90s a few Blazers home games weren't televised. Allen would pay for a full broadcast, replete with stats and replays, for an audience of one. The player of the game, Paul, is Clyde Drexler! Sometimes Allen would be traveling during the telecasts. No problem. He would pay for them to be beamed to a satellite and then, in the manner of a crisp bounce pass, back down to his yacht. "The more I realized the challenges and opportunities," says Allen, "the more I got into it."
It was natural to wonder why a man of the mind and a fierce introvert would want to insinuate himself into the back-slapping, towel-snapping culture of big-time sports, especially as team owners were becoming increasingly public figures. The armchair psychoanalysis went like this: Here was Allen's chance to buy membership in the popular clique he couldn't penetrate as an adolescent. "He finally got to be a jock, be in the cool crowd," says a former Blazers executive who, like many ex-employees of Allen's, will speak about him only on condition of anonymity. "It was a Revenge of the Nerds thing."
That explanation may bear some truth, but it's inadequate. If Allen simply wanted to buy his way into the cool crowd, wouldn't he be a more conspicuous presence, living La Vida Jerry Buss? Instead he's always operated at a remove. And if this were simply about ego and social status, would he really be memorizing reams of data about obscure draft prospects?
"It was like a high-tech puzzle to him," says Greenberg, now the men's basketball coach at Radford University in Virginia. "I think he was fascinated by whether he could figure out the data. He'd accumulate all this information. He'd crunch it and sort it and see if he could make the right decisions. I think the whole process of basketball—the combinations on the court, the decisions, the personnel—really intrigued part of his brain."
Allen also appeared to be entranced by the players themselves. He is a lifelong bachelor—he shares the Mercer Island compound with his mother, sister and brother-in-law—and has never had children. Many current and former Allen employees claim it's no stretch to suggest that these tall men in jerseys become like offspring to him. He may rarely communicate with them, but, Lord, does he ever provide for them. When private planes became the preferred mode of travel, the Blazers' was the most lavish. He made sure the club had a nice home: Without any public funding or even naming-rights revenue, Allen spent $262 million to build the Rose Garden, which was the NBA's premier arena at the time of its opening, in 1995. He conferred all kinds of amenities on the players and gave them contracts akin to fat allowances. "I've come to learn that he really thinks of these guys as his players," says McMillan. "When he talks about the Blazers, it's like a fantasy."