Scottie Pippen has arguably seen it all in basketball. Apart from a successful 17-year career in the NBA, he is also a huge fan of the sport. The Chicago Bulls legend won six NBA championships together with Michael Jordan. Pippen was a seven-time All-Star and a member of the All-Defensive team ten times.
On Sunday, he engaged basketball fans with a simple post on X, formerly Twitter:
“Which one would you have rather seen happen?”

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The four photos are considered four of the biggest what-ifs in NBA history. The first one involved Derrick Rose who couldn’t sustain his meteoric rise to stardom due to a devastating knee injury. Rose’s first four years were electric, winning MVP when he was only 22 years old. He never regained his form after suffering an ACL injury that forced him to miss one season.
Next on Scottie Pippen’s list was Chris Paul’s trade to the LA Lakers which was vetoed by David Stern. The late NBA Commissioner acting as the Charlotte Hornets’ de facto owner scuttled a three-team deal that would have allowed Paul to team up with Kobe Bryant and Pau Gasol in LA. The Lakers had won back-to-back titles before the “CP3” situation. They would have been favorites to make it a three-peat if that trade went through.
Third on the list was the fearsome trio of Russell Westbrook, James Harden and Kevin Durant. The trio led the OKC Thunder to the 2012 NBA Finals but lost to the Miami Heat. Harden, however, wanted a more lucrative contract forcing Oklahoma to trade him to the Houston Rockets.
Had the three of them stayed for a few more years, they might have broken through and the Warriors dynasty might not have happened.
Finally, Scottie Pippen brought up the LeBron James duel against Kobe Bryant in the NBA Finals that never happened. The “Black Mamba” was in his eighth season and in the prime of his career when James jumped from high school to the pros. Unfortunately, fans never saw the two superstars go head-to-head in a championship series.
Pippen did not say which what-if he would have wanted to see happen, though.
Fans react to Scottie Pippen’s “what-if” list
It didn’t take long for fans to react to Scottie Pippen’s interesting list of four of the biggest what-ifs in NBA history.
“Derrick Rose never getting injured”
One fan commented:
“Easy. Cp3 in purple and gold. There are no what-ifs about an injury, or hypotheticals, it would have been so magically pretty. But unfortunately wasnt allowed.”
@minithatgoat had a different pick:
“Never split up they would have 3+ championships today”
Another fan brought up an option that wasn’t on Scottie Pippen’s list:
“Healthy Hill and Duncan goes to Orlando with Tmac. That’s my pick.”
Pippen himself was involved in one of the biggest what-if moments in NBA history. Would the Chicago Bulls have won eight straight championships if not for Michael Jordan’s sudden retirement? That is an option that might have stirred a more passionate debate than the ones on his list.
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