Heading into the 1997-98 season, Scottie Pippen was a 10-year veteran who received an All-Star berth in seven of the previous eight years, a selection to either of the three All-NBA teams in every season since 1992, and had been on an All-Defensive Team since 1991.
In other words, there were few players around the league that could compete with the accolades accumulated by Pippen.
And yet his salary was far from reflecting that reality.
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The Bulls' 1997-98 roster had Michael Jordan as its highest-paid player, earning nearly $33 million. Among the others, Ron Harper and Tony Kukoc were second with $4.6 million followed by Dennis Rodman ($4.5 M) and Luc Longley ($3.2 M).
And Pippen? He was sixth earning 2.8 million dollars for that season.
How do you explain one of the great players in the league and a man, who in 1996 had been chosen among the 50 best players in NBA history, to be the sixth-highest paid player on his own team? Easy, the signing of an unfavourable contract in 1991.
After his first four years on rookie salary, it was time for Pippen to re-negotiate his contract with the Bulls prior to the 1991-92 season. He had already been established as Jordan's sidekicks and one of the greatest young players in the league.
The Bulls' offer, which was accepted by Pippen, seemed to reflect the confidence they had in him: seven years and $18 million, with a salary ranging from $2.2 to $3.4 million.
Pippen would earn $2.8 million for the 1991-92 season, making him the 16th highest-paid player in the league and a close second to the $3.2 paid to teammate Jordan. So far so good, but of course, with time the landscape changed completely.
What was in 1991 regarded as one of the best contracts in the NBA, was outdated by 1997. In fact, Pippen was not only the sixth highest-paid player on his team but the 122nd highest-player in the league. Players like rookie Tim Duncan and Michael Williams, who barely stepped on the floor, earned more than him.
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The Last Dance, a documentary that released its first two episodes on Netflix this past Monday, gave us Pippen's perspective as he justified the signing of the extension in 1991: "I felt like I couldn't afford to gamble myself getting injured and not being able to provide. I needed to make sure that people in my corner were taken care of."
Pippen never got injured and proved to be quite durable between 1991 and 1997. In the six years of this contract, he missed just 19 regular-season games, starting 473 of a possible 492.
This contractual situation was one of the reasons for the break-up in Chicago. In conflict with management, Pippen waited until the start of the 1997-98 regular season to undergo foot surgery. The delayed surgery cost him the first 35 games of the season and broken down any remaining bridges with general manager Jerry Krause and the front office.
After the sixth title in Chicago in 1998, Pippen was acquired by the Houston Rockets, via sign-and-trade, making him the 10th highest-paid player in the league and sixth-highest in 1999-2000 (for the Portland Trail Blazers).
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