Scottie Pippen: The Greatest Sidekick or the Most Underrated Star of His Era?
History often paints Scottie Pippen with a single brushstroke: Michael Jordan’s sidekick. It’s a convenient label — clean, simplistic, and easy to digest. But reducing a Hall of Famer and 6-time NBA champion to a supporting character in someone else’s story is like calling Robin just Batman’s chauffeur. Pippen wasn’t just a sidekick — he was the glue, the anchor, the perimeter terror, and arguably the most versatile two-way player of the 1990s.
Yes, he played second to Jordan during the Bulls’ dynasty years, but that second chair came with immense responsibility. He guarded the best offensive player, initiated the offense, and carried the team emotionally when Jordan retired the first time. In 1993-94, with Jordan retired, Pippen led the Bulls to 55 wins, finished third in MVP voting, and came one questionable call away from the Eastern Conference Finals. That’s not a “sidekick” season — that’s a superstar performance.
Still, the narrative of Pippen as a perennial No. 2 stuck — and his post-Bulls journey did little to shake it. After being traded to the Houston Rockets in 1998, Pippen joined forces with two aging legends: Hakeem Olajuwon and Charles Barkley. Clyde Drexler had already retired by then — despite popular misstatements — and the Rockets were chasing one last shot at contention. On paper, it was a superteam. In practice, it was a collision of fading timelines and clashing egos. The 1998-99 lockout-shortened season ended with a swift first-round playoff exit at the hands of a rising Lakers squad led by young Shaquille O’Neal and Kobe Bryant.
Pippen’s Rockets stint was brief and chaotic. He publicly clashed with Barkley, criticized the team’s culture, and was traded to Portland after just one season. There, in 2000, he once again found himself cast in a secondary role — this time to Rasheed Wallace, the Blazers’ volatile but ultra-talented forward. And yet, it was in Portland that Pippen’s veteran presence almost shifted the balance of power in the West.
The 2000 Western Conference Finals between the Blazers and Lakers remains one of the most legendary series in modern basketball history. Pippen, now older but still a defensive savant and floor general, helped push the Shaq-and-Kobe Lakers to a brutal 7-game war. Portland led by 15 in the fourth quarter of Game 7, on the brink of dethroning the next great dynasty before collapsing under the weight of history and a furious Lakers comeback.
So yes — Pippen has spent much of his career in the shadow of greatness. But he was never merely a shadow. He was the architect beneath the spotlight, the one who made stars shine brighter. Whether beside Jordan, Olajuwon, Barkley, or Wallace, he adapted, defended, facilitated, and competed.
In the end, calling Pippen just a “sidekick” is like calling an engine just a part. Technically true — but hopelessly incomplete.
Let me know if you’d like it rewritten in the tone of a sports debate show, fan forum, or fictional sports docuseries!
