Scottie Pippen was consistently underpaid in his time with the Bulls from 1987-98, an issue that was highlighted throughout ESPN's documentary 'The Last Dance'. Pippen feuded with former Chicago general manager Jerry Krause for much of the 1990s, and entering 1997-98, Pippen knew it would be his last season with the Bulls.
Pippen and the Bulls captured their sixth championship in 1997-98, ending one of the greatest team runs in NBA history. So where would Pippen play next? The seven-time All-Star found himself closing out the 1990s with the Rockets.
The move to Houston was largely a financial decision for Pippen, who was aided by Krause in an attempt to finally cash in on a Hall-of-Fame career. Rather than sign a four-year, $45 million deal with a new team, Pippen inked a five-year, $67 million deal with Chicago before being traded to Houston. The Rockets gave up bench forward Roy Rogers and a second-round pick, and in return, they received one of the greatest forwards in NBA history.
So why did Krause–who was often a target of Pippen's taunts–aid Pippen's move to a new team? Consider the move a "going-away present."
"By doing a sign-and-trade with Houston, Scottie could get more than $20 million more than he could by just signing a straight-out contract," Krause wrote in an unpublished memoir obtained by NBC Sports' K.C. Johnson "[Owner] Jerry [Reinsdorf] and I gave him his going-away present. I called Steve [Kerr] and Jud [Buechler] and told them the situation and to take the first good contract they could because we were not going to bid for them. They deserved it."
Pippen finally earned a salary commensurate with his talent in the summer of 1998, but upon joining the Rockets, his performance cratered. He averaged just 14.5 points per game–his lowest mark since 1988-89–and he shot a middling 43.2% from the field. Pippen feuded with then-teammate Charles Barkley in the 1999 offseason, paving the way for his exit before a trade to Portland.
Houston lost to the Lakers in the first round of the Western Conference playoffs in 1999, a series in which Pippen tallied 18.3 points and 11.8 rebounds per game. But the solid playoff performance couldn't salvage his time in Houston. Pippen was dealt to the Blazers five months later, kickstarting a minor rebuild for the Rockets. Houston would miss the playoffs in each of the next five years before returning to the postseason in 2004.