In the mid-1990s, the Orlando Magic looked on their way to becoming an Eastern Conference powerhouse, ready to take over from or dethrone the Chicago Bulls. Unfortunately, some probable internal turmoil and Shaquille O’Neal seeking greener pastures and leaving Penny Hardaway curtailed the franchise’s plans.

Still, the O’Neal-era Magic was a force to be reckoned with, especially because the big man’s tandem with the up-and-coming Hardaway proved tough to stop. Even Michael Jordan was said to have been “frustrated” at guarding the former Magic star, according to the Chicago Bulls legend’s 1984 Olympics teammate Jon Koncak

“I played with Michael Jordan on the ’84 Olympic team,” Koncak said. “We got to know one another pretty well that summer and were friends throughout our playing career. It was the first time that I’d ever seen Michael have a difficult time guarding someone. I vividly remember Michael being so frustrated that he couldn’t stop him.”

Outscoring MJ

Considering that Koncak played just one season with Orlando, the 1995-96 campaign, to be exact, the game he was presumably referring to was their first bout versus the Bulls that year.Chicago was likely out for vengeance that evening, having been eliminated by Hardaway and company in the previous playoffs. Interestingly, that was the Bulls’ only postseason series loss from 1991 to 1998 with Jordan on the team.Penny once again spoiled Chicago’s plans, scoring 36 points on 12-for-18 shooting from the field. The Magic also won 94-88, dealing the Bulls the first of their 10 regular-season losses in that campaign.

MJ continued to find it difficult to contain Hardaway in the regular season, as the supposed heir apparent to “His Airness” averaged 25.0 points per game in the next three meetings. The five-time MVP had the last laugh, though, as Chicago triumphed in those contests.

Showing Penny who’s boss

An interesting turn of events occurred in the 1996 playoffs as the two teams converged again in the Eastern Conference Finals.

Hardaway personally got off to a good start in the round, recording 38 points in the series opener. Unfortunately, he and O’Neal, who scored 27, received virtually no help from their teammates, who combined for just 18 points. The Bulls prevailed 121-83.

Jordan helped make life hell for the former Memphis Tiger for the rest of the series, as Chicago limited the four-time All-Star to 38.3% shooting in Games 2 to 4. The round ended in a sweep, with Mike putting the finishing touches by racking up 45 points in the elimination match.

After that season, Hardaway’s career started going downhill because of O’Neal’s departure in free agency and his constant battles with injuries. Sadly, the supposed rivalry and the passing of the baton between the two iconic guards never took place.