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Top 10 Rockets “Could Have Beens”: #8 Scottie Pippen

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This entry has two “Could Have Been” tales wrapped up in one.

Scottie Pippen #33

After Clyde Drexler retired in 1998, the Houston Rockets thought they had found his perfect replacement. With both Hakeem Olajuwon and Charles Barkley still effective, yet aging fast, the Rockets knew they had a very short window left with those stars at the helm. So they swung a trade in the offseason for forward Scottie Pippen, who was coming off of his second set of three straight titles alongside Michael Jordan with the Chicago Bulls.

Pippen’s defense and willingness to fit in a secondary role alongside Houston’s two big post threats was thought to be a perfect fit, and when the Rockets sent Roy Rodgers and a 2000 second-round pick to the Bulls for Pippen, the trade rightfully received much publicity and fanfare.

And in the shortened 1998-1999 season, Pippen and the Rockets didn’t necessarily disappoint, but this is still a classic case of what could have been.

Pippen played pretty good ball in his lone year in H-town. He averaged 14.5 points, 6.5 rebounds, 5.9 assists, and 2.0 steals per game, which was the type of well-rounded line the Rockets were looking for when they brought him in for the third-piece role.

And the team achieved some success also. Despite a lack of quality depth behind their three big names (only Michael Dickerson and Cuttino Mobley gave real contributions), the Rockets finished with a 31-19 record and with the fifth-seed in the Western Conference.

Nonetheless, there were issues. The biggest of which were Pippen and Barkley mostly at each other’s throat. Barkley felt Pippen was too rigid, and Pippen felt that Barkley had gotten lazy and wasn’t fully invested in team success. And both, to some extent, were true.

Despite their differences, they headed into a first-round playoff matchup with the Shaq-Kobe Los Angeles Lakers, and a Rockets team with chemistry issues was no match for that group, even if L.A. had yet to realize the full extent their powers.

Pippen averaged a robust 18.3 points, 11.8 rebounds, and 5.5 assist per game in the series, but he also shot just 32 percent from the field. An aging Olajuwon struggled against a Shaq who was just entering his prime, and despite showing some heart in a big Game 3 victory, the Rockets fell 3-1 in the best-of-five series.

In the offseason, the Pippen-Barkley feud exploded, with Pippen eventually requesting a trade. Barkley then went public, saying:

“For him to want to leave after one year, it disappointed me greatly. The Rockets went out of their way to get Scottie and the fans have treated him well, so I was just disappointed in him.”

While Pippen had this to say in response:

“He’s a very selfish guy. He doesn’t show the desire to want to win. I wouldn’t give Charles Barkley an apology at gunpoint. He can never expect an apology from me, if anything, he owes me an apology for coming to play with his fat butt.”

Who knows what really could have been had Pippen and Barkley gotten along or had Sir Charles still been working as hard as he did earlier in his career. Sure, Houston’s big three were all technically past their prime, but they made it as far they did with a rotund Barkley, a disgruntled Pippen, and an Olajuwon essentially stuck in the middle. If all three were engaged and playing together, you couldn’t count out that talented trio.

Which brings us to the second “Could Have Been” in the Pippen story.

With Rockets management realizing how soon the sand would be out of the Olajuwon-Barkley hourglass, and Pippen essentially refusing to play another moment alongside Sir Chuck, Houston sent Pippen to the Portland Trail Blazers for a cadre of guys meant to refill the Rockets’ shallow pool of depth, provide ammunition for other deals or be released for cap space.

In exchange for Pippen, the Rockets received Stacey Augmon (who the Rockets waived and then re-signed with Portland), Kelvin Cato (who was meant to help fill the void an aging Dream was leaving in the paint, but who failed to ever average double-digit points or rebounds), Ed Gray (who never played another minute of NBA action), Carlos Rogers (who averaged 6.5 points and 4.5 rebounds in two seasons with Houston before being left to walk in free agency), Brian Shaw (who was immediately released by the Rockets and signed by the Lakers), and Walt Williams (who averaged 9.4 points and 3.6 boards in three seasons with the team before leaving in 2002 for Dallas).

Despite teams knowing Pippen wanted out of H-town, Houston’s failure to get even one serviceable player or a draft pick when trading a Hall of Famer makes this an extra special “Could Have Been.” Not only could the Rockets have been better had Pippen and Barkley gotten along, but Houston also could have set themselves up a little better for the future when trading Pippen. It’s a double-dip “Could Have Been”, coming in at #8.