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“Scottie Pippen is the only guy I’m jealous of because he played with Michael Jordan”: Kenny Smith expresses his regret over being picked one spot after the Bulls legend

Samir Mehdi

“Scottie Pippen is the only guy I’m jealous of because he played with Michael Jordan”: Kenny Smith expresses his regret over being picked one spot after the Bulls legend

Kenny Smith dishes on how Scottie Pippen getting picked one spot ahead of him robbed him of the chance of playing with Michael Jordan. 

Michael Jordan lost in the first round of the Playoffs 3 consecutive years before Scottie Pippen landed on the Chicago Bulls roster. After losing to Sidney Moncrief and the Bucks in ‘85 and to Larry Bird’s Celtics in 1986 and ‘87, it was time for Jordan to take the next step in his Playoff journey and Pippen was instrumental in that happening. 

The 1987 NBA Draft was probably the best draft the Bulls had in the Michael Jordan era beside of course, the one where the drafted MJ himself. They made a draft night trade with the Seattle Supersonics to move up from the 8th pick in the draft to the 5th pick, a pick that the Supersonics held.

Also read: “Michael Jordan would score at will from the perimeter and I would in the paint”: When Kareem Abdul-Jabbar dished on who would win in a 1v1

Seattle wanted a big-man to strengthen their front-line and so decided to go with 6’11 Olden Polynice. The Bulls on the other hand, wanted to get the ball out of Michael’s hands on possessions, reducing his offensive burden. 

So, they looked to draft point forward, Scottie Pippen, who Seattle selected for the sole purpose of trading to the Bulls. Chicago would get one more selection in this draft at the 10th spot and they used to it take Horace Grant, a man who contributed heavily to their first 3-peat from 1991-93. 

Kenny Smith on Scottie Pippen getting to play with Michael Jordan. 

Playing alongside Michael Jordan meant you were on a trip to the postseason in every single one of your seasons with him, with a Finals trip more likely than not. Kenny Smith recognized this and was looking forward to playing with him as the Bulls were in the range to draft him in 1987. 

Unfortunately for him, Scottie Pippen was picked 5th by the Bulls and he was chosen 6th by the Sacramento Kings, one pick behind what could’ve been residency in Chicago instead of Sacramento.

Also read: “I don’t have friends!”: When Kobe Bryant shared the nature of the competitive relationship the Black Mamba had with His Airness, Michael Jordan

‘The Jet’ says that he was jealous of Pippen for being selected by the Bulls instead of him due to the fact that he got to play with Jordan and not him. [around the 3:22 mark] 

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The best point guard Michael Jordan ever played with was BJ Armstrong so having a guy like Kenny run point for him would’ve been a massive upgrade for him at that position. 

It wasn’t all doom and gloom for Kenny as he eventually played with the man who was picked ahead of MJ in 1984, Hakeem Olajuwon, winning back-to-back chips with him in the process. 

About the author

Samir Mehdi

Samir Mehdi


Samir Mehdi is a senior strategist for the NBA division at The Sportsrush. Ever since he was 13 years old, he’s been obsessed with the game of basketball. From watching Kobe Bryant’s highlights on YouTube to now, analyzing and breaking down every single game on League Pass, Samir’s passion for the game is unwavering. He's a complete basketball junkie who not only breaks down current games but also keenly watches ones from the 60s’ and 70s’ while also reading comprehensive books on the history of the league. Samir’s life revolves around basketball and he hopes that shows in his work. Aside from work, he loves to spend time in the gym and with his friends at social gatherings.

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