“Everybody asks me that, and they say, ‘Why not Michael Jordan?'” – Gary Payton on why he always said John Stockton was his toughest matchup originally appeared on Basketball Network.
Gary Payton was one of the most in-your-face defenders of his era.
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And what an era it was, an unforgiving stretch of the ’90s and early 2000s where Hall of Famers came in clusters. The league was flush with sharpshooters, athletic freaks and cerebral assassins from Michael Jordan to Kobe Bryant, Allen Iverson, Tim Hardaway, and the list goes on.
Yet even in that crowd, Payton has always singled out one name as the toughest matchup of his career — Utah Jazz legend John Stockton.
Toughest matchup
Payton’s reputation wasn’t built on flair or highlight steals. His greatness lay in his ability to smother opposing guards, disrupt their rhythm, talk them into discomfort and make every possession a grind. While Jordan was everyone’s toughest matchup, the Seattle Supersonics legend chose a different route.
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“John Stockton. By far,” Payton said, reflecting on his toughest player to guard. “Everybody asks me that, and they say, ‘Why not Michael Jordan? Why not Kobe Bryant?’ Now, they were smart guys. They’d go to spots because they ran a triangle. They’d go away at one spot and I could meet them there.”
Jordan and Bryant were two players who made Phil Jackson’s triangle offense work like a charm. However, their predictability within the structure of the triangle offense is what Payton said he could read and react to. But Stockton didn’t operate from a pre-drawn map. He flowed, shifted gears, played like a quiet storm and defenders were often caught in the eye of it.
The Utah icon wasn’t a volume scorer like Jordan and the likes, but he brought an edge to the offense that Payton couldn’t easily shake. In his Defensive Player of the Year season, the ultimate showdown came in the 1996 Western Conference finals.
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The Jazz, led by the Stockton-Malone duo, were one of the most formidable teams in the league. Stockton was running the Jazz offense with every screen, every cut, every motion starting and ending with his read.
The Supersonics had clawed their way to the top seed and Payton had cemented his status as the league’s premier on-ball defender. And there, at the heart of that intense playoff collision, stood Stockton.
That 1996 series was everything that made him hard to guard. He wasn’t interested in beating Payton with brute force. He wanted to make him think and sweat the small stuff.
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Stockton’s edge
Stockton came into the league in 1984, the same draft class that birthed Charles Barkley, Hakeem Olajuwon and Michael Jordan. From the jump, he carried an aura of anonymity — short shorts, quiet demeanor and a disarming simplicity in his game. Yet underneath that mild exterior was a competitor who never let his foot off the gas.
Stockton led the NBA in assists for nine consecutive seasons. That level of dominance, especially at a position that demands orchestration, is rarely seen. He wasn’t scoring 30 a night like Jordan, but he controlled the pace and pulse of every game he played.
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Stockton never needed volume to dominate. His movements were subtle, yet surgical. Payton’s battles with most stars involved strength, speed or mind games. With Stockton, it became a test of endurance and detail.
“But John Stockton would go up a bit here, move away here, come on again,” Payton said. “He’d fool you, try to go back. And that was the thing I loved about him. He made me competitive. He made me be on my toes for all 48 minutes when he was in the game. He was a big, big deal for me to guard because he always kept me on my toes.”
Even so, Stockton’s greatness was rarely celebrated with the same fervor. Playing in the same era as Jordan came with consequences. The Jazz made back-to-back Finals appearances in 1997 and 1998, only to fall to the Chicago Bulls both times. The narrative of Jordan’s dominance became so towering that players like Stockton became footnotes.
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But among peers, there was never confusion. Payton’s respect was built on knowing what it took to stay locked in every second a man was on the court. Stockton never gave defenders the luxury of relaxation. There were no days off when he was on the floor. And for someone like Payton — who thrived on breaking opponents mentally — that presented the ultimate challenge.
This story was originally reported by Basketball Network on Aug 3, 2025, where it first appeared.