After Scottie Pippen won the sixth title, serving as a "Robin" to Michael Jordan's "Batman" and feeling like he was often in the shadow, he decided to try his luck somewhere else. And in a 1999 sign-and-trade deal, he was shipped to the Houston Rockets .
On paper, the team consisted of Hakeem Olajuwon and Charles Barkley , both former MVPs, with Pippen holding fort; it looked promising (for a brief moment). But soon enough, it became clear that even superstars in decline, all coming together, wasn't enough to tip the scales in their favor and aim for a championship.
Although Pippen himself admitted he wanted to help Barkley win his first ring to have something to show for it, the failed relationship between the two forwards ultimately led to Pip's quick departure from H-Town.
If we circle back, even though Pippen undoubtedly did want to win a chip without MJ, he had nothing left to prove to the naysayers. After all, he was touted as one of the best defenders in the entire league, capable of taking over when the situation required it, with or without Jordan.
But he quickly understood that the situation was entirely different once he set foot in Houston and saw that Barkley would be a whole different beast to run with. And no, this time, not in a good way.
Scottie firmly believed that Chuck did not put enough work into his craft and was overweight and lazy, which further disappointed him, as he felt he had wasted a year of his career chasing nothing. They were supposed to be a serious team, with an experienced trio expected to be among the main contenders. In the end, it was anything but, and Pippen made his feelings known after Barkley publicly criticized him after a subpar playoff series against the Los Angeles Lakers in 1999.
"I wouldn't give Charles Barkley an apology at gunpoint," Scottie responded to Chuck's criticism. "If anything, he owes me an apology for coming to play with his fat butt."
It was over. That was a clear indication that this was not going anywhere, and Sir Charles, always ready to butt heads both on and off the court, did not stay silent. Instead, he responded in his own unmistakable fashion, which, looking back, sounded like a threat.
"He said he would never apologize. But, as you know, I always carry a gun with me," Barkley said while having the whole room full of reporters laughing. "So, there is a chance. There is a chance. I'm going to go to my truck and get my gun and see. So, if I get arrested for murder, ya'll will know he didn't apologize."
To put it simply, two Hall of Famers did not find their rhythm together. The verbal jabs and constant tension quickly made it clear that things were getting out of hand. Both of them thought they were right, and probably none of them truly was.
A 33-year-old Pippen, a 35-year-old Barkley, and a 36-year-old Olajuwon were supposed to be a superteam, but it never quite lived up to expectations. They were knocked out in the first round and never played together again. Scottie went to the Portland Trail Blazers to chase another ring, while Barkley stayed in Houston for another season.
Even though their beef briefly resurfaced years later, Barkley's controversial "gun" remark never came to fruition. Thankfully.
This story was originally published by Basketball Network on Apr 13, 2026, where it first appeared in the Old School section. Add Basketball Network as a Preferred Source by clicking here.
