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Much in the same way he pimped his yacht, Allen pampered his beloved Blazers. As Holmgren puts it, "All sports team owners are wealthy, but Paul's in another league." Urged on by his consigliere in the late 1990s, team president Bob Whitsitt, Allen made a transparent attempt to buy an NBA title. He lavished on players contracts that were wildly disproportionate to the players' value.
An out-of-shape, drug-addled Shawn Kemp commanded $12.7 million a year. Undersized point guard Damon Stoudamire checked in at $12.4 million. An aging Scottie Pippen came to Portland with four years left on a contract which would pay him $54 million. Despite playing in one of the NBA's smallest markets, the Blazers had the league's highest payroll. The luxury tax was merely an annoyance. Inasmuch as these were his kids, Allen was a sugar daddy, spoiling them rotten. It wasn't uncommon for them to emerge from practice and discover that "Mr. Allen" had hired someone to wax and buff their Hummers and Escalades.
The wild spending trickled down to the Blazers' offices, where employees created the acronym SPAM: Spending Paul Allen's Money.
"Should we buy the functional copier or the color copier with the bells and whistles?' "Let's get the color one."
BY THE middle of this decade, times were tough, relatively speaking, for the House of Allen. On paper, anyway, his vast fortune had declined by more than half as the tech bubble burst. Few of his quixotic investments had paid off. He had sold some of his valuable assets too soon and kept duds for too long. Executive turnover at many of his companies was high. His big bet on Charter Communications, one of the country's largest cable operators, was costing him billions. The Blazers alone were losing $100 million a year.
While a net worth of $16 billion doesn't exactly reduce a man to eating Top Ramen, Allen may well have lost more money than anyone in the history of humankind. Wall Street had a laugh at the eccentric "accidental zillionaire," noting that had he simply held on to his Microsoft stock—that is, had he adopted no investment strategy whatsoever—his net worth would have exceeded $80 billion.
But perhaps even more distressing to Allen than his financial losses was the fate of the Blazers. His attempt to buy an NBA championship had backfired spectacularly. The most impressive collection of athletes, unlike one of World War II planes or rock and roll memorabilia, isn't always the best. The Blazers may have had the highest-paid talent, but they had no cohesion. With Allen looking on like an eager stage parent, his high-priced teams ritually failed in the postseason.
Worse, the spoiled players found new and creative ways to embarrass the franchise. From J.R. Rider and Rasheed Wallace to Ruben Patterson and Qyntel Woods, they appeared often enough on police blotters to be known as the Jail Blazers. Last season Zach Randolph, the highest-paid player in Blazers history, missed a game because he was granted a bereavement leave to attend the funeral of his girlfriend's cousin. The night of the game, however, Randolph was hardly the picture of grief as he stopped by a strip club and allegedly left without paying his tab. The fans had become alienated long before that. The team that holds the longest consecutive sellout streak in big league sports history—814 straight games between 1977 and '95—was playing to pastures of empty seats. Time was, NBA officials would dispatch prospective expansion-franchise buyers to Portland to see how a model organization was run. Suddenly, under Allen, Portland had become the NBA's Exhibit A for how not to run a team.
Allen, friends say, felt betrayed. These, after all, were his players. "The Jail Blazers were distasteful to [the point] you didn't want to be associated with them. He felt it as much as anyone," says Maurice Lucas, who played 330 games with Portland and is now an assistant coach under McMillan. As Allen himself says with unmistakable anguish, "I feel like I went [with] the theory of talent over character. I was like, 'O.K., let's try that.' [But] when you go down that road, it's easy to go way too far down, and in the end it was a mistake."