Gary Payton highlighted the two toughest players he ever had to go against: "I knew I would learn something"

Gary Payton is one of the most competitive players of his time. However, he also recognized the skills of his fiercest rivals as much as he was confident about his game.

For Payton, two legends gave him the toughest matchups of his career were John Stockton and Michael Jordan.

It’s no surprise that even after years since he last took on Jordan and Stockton on the court, Payton still remembers how it felt to compete against the pair. According to The Glove, it was always a learning experience whenever he went toe-to-toe against them.

“I remember me and him [Jordan] jawing together. We always had great battles. That’s what brought it out in me. Him and John Stockton were the two guys I always looked forward to playing against because I knew I would learn something,” Payton once reflected.

Payton really beat MJ and Stock in trash-talking

More often than not, Payton didn’t get the better of Jordan and Stockton in their on-court duels. MJ won 14 times in their 21 head-to-head matches, while Stockton holds a 38-32 winning record over him.

Nevertheless, Payton isn’t salty about his defeats.

If anything, he looked back at those encounters with a deep sense of fulfilment and pride, knowing that he didn’t lose to just another player in the league.

Moreover, Payton knows that neither Jordan nor Stockton was able to match him when it came to one aspect of basketball.

“I was the better trash talker, of course,” GP further said with a smile.

Payton picks Stockton over MJ

Between Payton’s top two picks, it was Jordan who prevented him from winning an NBA championship.

Just when GP thought that his team, the Seattle Supersonics were on a roll, MJ and the Chicago Bulls beat them in the 1996 Finals.

However, Payton has stated on more than one occasion that when it comes down to Jordan and Stockton, he considers the Utah Jazz legend as the tougher matchup of his career. According to him, there was no doubt Jordan would be Jordan but Stockton’s efficiency and consistency were on a whole another level.

“I got to guard him 94 feet. I got to think about coming off of picks, he’s throwing passes, he’s coming back trying to steal basketballs, he’s always moving, he’s taking charges on me, he’s doing a lot of things. I have to always focus on him,” Payton once said on Vlad TV.

“He only played 34 minutes… And then when you look up, he shot the ball 10 times, he made eight,” GP added of Stockton. “He shot seven free throws; he made all seven. Next thing you know, you look up, he got 16 assists. Then you think about it and you say, ‘Dang, he got five, six rebounds and he got five steals.’ And I look up there and I say, ‘He got 27, 16, 5, 5.’ I can’t deal with that. And we getting beat by 20,” he concluded.

Payton was on point with his reflections.

In fact, it’s quite fascinating that GP recalls his past rivalries with MJ and Stockton without sour grapes, even though we know what a competitor he was in his time.

It seems like time heals all wounds in Payton’s case.

This story was originally reported by Basketball Network on Sep 8, 2025, where it first appeared in the Old School section. Add Basketball Network as a Preferred Source by clicking here.

Gary Payton highlighted the two toughest players he ever had to go against: “I knew I would learn something”

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