Throughout his 17-year-long NBA career, Scottie Pippen had worked alongside some of the most iconic and successful figures in the NBA, including Michael Jordan, Coach Phil Jackson, and GM Jerry Krause, without ever feeling intimidated.
However, his demeanor notably changed after he joined the Portland Trail Blazers in 1999. The seven-time All-Star no longer prioritized scouting his opponents before the game but wanted to observe one person in the stands - franchise owner Paul Allen.
Pipp was in awe of Allen
Allen was an extraordinary figure in the business world, having co-founded Microsoft Corporation with Bill Gates, produced films, engaged in research, and invested in high-profile ventures, among other expeditions. Consequently, his business acumen had garnered him a net worth exceeding $20 billion .
While most basketball players typically emulate those whose playing style they admire or wish to learn from, Pip’s approach was more unconventional. After being underpaid throughout his peak years with the Chicago Bulls, Scottie chose Allen as his role model and wished to seek advice on attaining billionaire status.
"What does he have? Forty billion? I want to know: How can I make a billion? " Pippen said . "I just want one of them! What do I need to do?"
However, the versatile forward was courteous not to overwhelm Paul with his inquiries. Instead, his strategy was to create a positive impression in Portland so that he would gradually develop an informal relationship with the owner. Ultimately, the six-time NBA Champ hoped this approach would allow him to gain valuable financial insights from the multi-billionaire.
"I don't want to approach him like that. I don't want people coming up to me just for what I do, and I'm sure he doesn't. So I have to let that relationship grow a little bit," Pip added. "Like, win a championship, and then I can say, 'Tell me how I can make a billion dollars. Tell me how I can become a billionaire.'"
Related: "That's not a goal I want to achieve. That's not something I think I'll be good at" - Allen Iverson on why he would never want to be a coach
Pippen created a positive impression on the owner
Despite being past his prime at 34 years old when he joined the Trail Blazers, ‘Robin’ demonstrated his enduring value as he averaged 12.5 points, 6.3 rebounds, and 1.4 steals per game, earning a place on the All-NBA Second Defensive Team. Moreover, his contributions were even more significant in the postseason as he improved his numbers on most fronts to help the Blazers reach the Western Conference Finals. Safe to say, it does seem that Pippen’s concerted effort was successful in creating a favorable impression on Allen during his inaugural season with the franchise.
However, the 6’8” forward may have waited too long to seek Paul’s advice, as he ultimately accumulated a net worth of 'only' $20 million over his career.
Related: "Frequently it was heated" — Steve Kerr claims Michael Jordan and Scottie Pippen's conversations in practice usually had tension
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