There were those like Dennis Rodman who wished and got to play alongside one of the greatest players of the time. Then there are those like Charles Barkley, who despite making Dream Team history, never got to be on the same NBA team as Michael Jordan. Chuck’s colleague is acutely aware of that feeling. Three years and a single draft spot made all the difference for Kenny “The Jet” Smith who had the privilege of calling MJ his teammate for their one overlapping NCAA season at Chapel Hill. But he never got his dream reunion while watching Scottie Pippen have the privilege of being Jordan’s tenured teammate.

Kenny, who’s better known for his knocked knees on Inside the NBA than two championships with the Houston Rockets, stopped by The Pivot Podcast to talk about everything from UNC to being the underrated Inside Guy next to Shaq and Chuck. Unfiltered as usual, he had no qualms confessing that he was jealous of Scottie Pippen long before he won a championship.

“I don’t think I’ve ever said this: for my first six years, I was always jealous of Scottie Pippen,” Smith confessed. “I was so jealous because I was a sixth pick. He was the fifth…” Pip and Kenny were both top picks in the 1987 draft class, only a spot apart. While it may sound like he was jealous that the Central Arkansas product got picked ahead of him, the real reason was because the Chicago Bulls picked Kenny’s fellow Tar Heel three years earlier. 

“I was so jealous because I was like, I knew what [Michael Jordan] could do and bring out of you. Like, you always have it in you, but you sometime you need somebody to like elevate it like to another level. And I knew that he would do that. And so I used to look at Scottie and be so jealous of that dude.”

Pippen was selected fifth overall by the Seattle SuperSonics and immediately traded to Chicago to team up with the future legend on the Bulls. Kenny went sixth to the Sacramento Kings. Kenny revealed he had even traveled to Chicago for a pre-draft interview with the Bulls’ front office. So the missed what-could’ve-been still stings for The Jet,

This professional envy eventually fizzled out as their vastly different professional paths crossed under drastically different circumstances in Houston. While Smith anchored the starting point guard spot for the Rockets’ back-to-back title runs in 1994 and 1995, Pippen didn’t arrive in Houston until a 1999  trade, after The Jet had retired in 1997 to transition to become the first permanent analyst of TNT’s Inside the NBA. In a weird turn of events, he became more famous for his sportscasting career than for being an NBA champion.

Kenny “The Jet” Smith made peace with Scottie Pippen and his jealousy

NFL star and Pivot host, Channing Crowder pointed out that Kenny and Jordan wouldn’t have yielded six championships together. Nor would we have have witnessed Pip’s dynamic growth despite early career hurdles like his infamous postseason migraines. Smith admitted it’s true but also fiercely defended his early career.

Kenny’s jealousy purely stems from an unfulfilled ambition to be Michael Jordan’s teammate. So he had to make it known that statistically he was no slouch in comparison to Scottie Pippen. “So my first three years, I was Kenny Smith. I’m First-Team All-Rookie,” Smith argued, emphasizing that he was averaging 17 to 18 points per game as a primary option on a rebuilding Kings squad while facing constant defensive double-teams.

Meanwhile Pip would take a while to make an impact on the Bulls squad. The natural analyst he is, Kenny claimed that Chicago’s early guard play heavily struggled against the Bad Boy Pistons led by Isiah Thomas, Joe Dumars, and Vinnie Johnson. “Not saying I would have did it all the time, but I could have beat those guys off the dribble at that stage in my career. And I was like, that’s what’s missing.”

While Kenny spent the first half of his basketball life looking over his shoulder at Pippen’s historic luck, his three-decade career in broadcasting has erased any lingering desire to be anyone else. Sitting on television’s most famous sports studio set alongside larger-than-life Hall of Famers Shaquille O’Neal and Charles Barkley, Smith is frequently asked if it fuels him negatively when younger fans don’t know he was an NBA star, or if he prefers his second act popularity.

“No. I think one, my lane of what I do on the show is very obvious,” Smith explained, detailing how he deliberately avoids looking at stat sheets to evaluate the game based strictly on visual impact. “It stands out. I get more credit for knowledge of basketball than I probably should even now. The way people revere what we do and what I do overtakes the fact that they might not have seen me at my best.”

Obviously, Kenny has a bigger impact on the game Racing (or hobbling) to the Board in Studio J. He’s found contentment sharing the soundstage with Shaq and Chuck now. He may have two chips, but he loves his sportscasting identity. At least that’s something Pippen doesn’t have.