Gary Payton is one of the best perimeter defenders in the history of the game, and he is the only point guard to ever win the Defensive Player of the Year award. He has guarded a lot of different players, including the great Michael Jordan.
One would expect that Michael Jordan is the hardest matchup that Gary Payton has had to take on. After all, he's widely viewed as the greatest player to ever play basketball.
However, Gary Payton claimed that a different player was more difficult than Michael Jordan himself. That player was John Stockton, who currently holds the all-time assists record. Gary Payton lauded John Stockton for being "fundamentally sound" and for making the right play every time.
If I could guard Michael Jordan one game and guard him to the fullest; I had to play John Stockton almost 13 times a year, even if we played them 6 times in the regular season and then going Game 7s in the Playoffs.
He was a guy who was fundamentally sound. He would set picks, he would do the right thing. He would shoot 12 times, make 10. He was great.
You guys didn't play against him, I did. If a guy come and shoot 12 times, makes 9 of them. Shoots 8 free throws makes 7 of them. That's 20 something points, and having 15 assists and 4 steals a game... that is hard to guard.
Michael Jordan he's a competitor. He's gonna go back at me, that is easier for me to deny him the ball and do a lot of things.
Michael Jordan once notably laughed at Gary Payton's defense during The Last Dance documentary, and it's clear that Jordan believes that Payton wasn't a problem for him as a defender. With that being said, Gary Payton definitely made life hard on Jordan at times when guarding him.
Most defenders from that era would disagree with Gary Payton's assertion that John Stockton is harder to guard than Michael Jordan. Michael Jordan is the greatest scorer to play in the game, but it is possible that someone like John Stockton would be more difficult for Payton to guard since he wouldn't just try to score on Payton in isolation and try to make the right play.