Joe Dumars
Michael Jordan has always said that his toughest 1-on-1 opponent was Joe Dumars. Jordan said that Dumars “thought well and forced his opponents into doing things that they weren’t comfortable doing”. It’s interesting to note that Jordan said that Joe Dumars was his toughest defensive assignment even though Dumars was shorter than Jordan and also did not have anywhere near the speed that Jordan had. Dumars one just one of the main pieces of the Bad Boy Pistons defense that gave Jordan hell in the Eastern Conference Finals three years in a row.
Gary Payton
Here is another guy who was slower than Jordan (although overall Payton was still super quick, just not as quick as Jordan), in this case much shorter than Jordan, and could not keep up with Jordan’s vertical leap. GP defended Michael during the 1996 NBA Finals, and when you go back and dig into the stats, Jordan’s worst games occurred when Payton was his defender. Many Sonics fans will say that had George Karl matched up with Michael Jordan from the opening game of the series instead of midway through the series, the outcome may have been different.
Reggie Lewis
This is a funny one because when you ask fans which players guarded the Chicago Bulls guard the best in his career, most of the time Reggie Lewis’ name comes up. There is even a highlight reel of him blocking Jordan four times in a single game in 1991. That really did happen. Not everyone can say they blocked the great Michael Jordan multiple times in a single game. However, the head-to-head stats tell a story that Jordan often played well and more specifically shot well against Lewis, averaging 35/6/6 against the late Celtics forward.
Bobby Phills
When you look at the numbers that Michael Jordan garnered while being defended by former Charlotte Hornets guard Bobby Phills, his numbers were actually lower than average. Phills held Jordan to 28ppg (2 points less than his career average, which is a big deal) and also held Jordan to multiple games where shot less than 50% from the field. It’s possible that Phills often times gave Jordan trouble because he was built more like an NFL linebacker than a basketball player.
Sidney Moncrief
MJ had a lot of respect for Milwaukee Bucks’ guard Sidney Moncrief and described Moncrief as, “chasing him all over the court.” Jordan mentioned that he was normally in for a long night with Moncrief guarding him, but when you dig deep into the stats of their head-to-head matchups, Jordan averaged right around his normal numbers across the board in all categories. So, while Moncrief may have made his job difficult over the years, Jordan still found a way to average 34 points per game against him.
Mitch Richmond
MJ has often said that his toughest defensive assignment was guarding Sacramento shooting guard Mitch Richmond. That statement is saying a lot as Jordan often guarded his opponents’ best shooting guards. The interesting thing about the head-to-head matchup is that Jordan often averaged less than his typical numbers when facing Richmond. Jordan said that it was difficult for him to guard Richmond, but never said that he had a difficult time offensively with Richmond defending him. We guess the numbers tell a different story.
Scottie Pippen
Michael Jordan versus Scottie Pippen? What the hell are you talking about? We know this is a strange one, but we just had to include it. We know, Michael Jordan only officially went head-to-head against Scottie Pippen once in 2002, when Jordan was playing for the Wizards and Pippen with the Portland Jailblazers. Something that definitely is noteworthy about that single matchup is Jordan only scored 14 points and was a -15 that game. A minus 15!!! But that’s not what this is about. Pippen guarded Michael Jordan pretty much daily during practices and learned his game and tendencies inside out. There are plenty of stories from former Bulls players of Pippen and Jordan having epic battles in practice.
Len Bias
We saved this one for last. The most interesting person of anyone on the list (Those of you who have been here before know about our obsession with Bias and you can read about him here https://picassobaby.com/2020/06/27/10-things-you-didnt-know-about-len-bias/). While they unfortunately never played each other in the NBA, Bias did face off against MJ in college during Jordan’s junior year. Although Bias and Jordan were never officially matched up, there were plenty of times throughout the game that the two defended each other. Fans have said that Bias did an amazing job against the UNC guard and guarded him the best of any of the other Terrapins. Bias was a few inches taller than Jordan, had a more muscular physique and could match Jordan’s unbelievable vertical leap. If anyone could have matched up with Jordan, it was for sure Bias. One could imagine what their NBA battles would have been like.