The 1999-00 season was a pivotal year for Kobe Bryant and the Los Angeles Lakers.

As for one, the young Mamba had quickly learned the ropes of NBA ball. The 17-year-old prodigy had morphed into a 21-year-old star ripe for greatness. As for the Lakers organization, the season marked their first year with legendary head coach Phil Jackson, who had just come back from a one-year sabbatical following his sixth NBA Championship with the Chicago Bulls.

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It was all coming together for the Lakers after years at the bottom of the Western Conference.

Jordan spotted

Excitement arose early in the 1999-00 season when Michael Jordan was spotted ahead of a Lakers game at the Staples Center. He headed straight to the locker room, which fueled rumors: Was he mounting a comeback? Or maybe eyeing a coaching position?

Michael quickly dispelled the gossip and said:

“I’m just visiting.”

However, Jackson soon revealed that there’s something deeper about Jordan’s visit that night. Jackson and Jordan’s special bond, formed through their journey to six NBA Championship rings, gave the Zen Master unprecedented access to MJ’s services.

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He wanted Mike to practice with the team — to share the nuances of the triangle, how to play the right way and maybe have a conversation with Kobe.

While Mike appreciated the invite, Jackson revealed the five-time NBA MVP declined, citing concerns about Bryant.

“He said he couldn’t do that,” Jackson said in 1999, via the Los Angeles Times. “He said, ‘Kobe [Bryant] is too dangerous in his present state.'”

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Kobe meets Jordan

Reporter Ahmad Rashad was also in the vicinity when Jordan visited his old coach and the Lakers. He witnessed the fabled encounter between the two legendary shooting guards and heard how Kobe challenged his idol to a one-on-one. Bryant didn’t care what Jordan had on his feet.

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“Kobe came in. Phil was trying to get Michael to come out to practice and show the guys something,” Rashad said. “So, I started instigating a little bit on who would win one-on-one. Michael was looking at him like, ‘Oh man, you’re a young fella.’ Kobe was like, ‘Look, I don’t know. You can just bring your tennis shoes. I can give you some tennis shoes, and we can play tomorrow.’ Kobe never backed off.”

It was in this moment that MJ realized Kobe was built differently.

Maybe the Bulls icon felt as if he was looking in a mirror. After all, early in his career, Jordan had a predilection for taking over games and resorted to one-on-ones instead of playing within the flow.

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It was only in his seventh year in the league that he learned to trust his teammates.

Mike realized Bryant was in the middle of discovering how to play team basketball within a structured system. Agreeing to a one-on-one would likely invigorate Kobe’s tendencies to play isolation ball. Like his idol, the Mamba was a gifted one-on-one player. He had the footwork, the tenacity and that irrepressible will to win.

Perhaps the Black Cat made the right decision to keep his leather shoes and not accept Bryant’s challenge. After all, Bryant showed remarkable improvement in the 1999-00 season. He became an All-Star, was named to the All-NBA First Team, All-Defensive Second Team and most importantly, won his first NBA Championship.

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It was the season Bryant proved he could play team basketball at a very high level.

Related: “That’s the thing that I saw” – Kobe Bryant revealed the greatest aspect of Michael Jordan’s game

This story was originally reported by Basketball Network on Sep 16, 2025, where it first appeared in the Old School section. Add Basketball Network as a Preferred Source by clicking here.