B.J. Armstrong on the night Kobe Bryant and Michael Jordan went at it — over dinner

B.J. Armstrong played with Michael Jordan, he played against Michael Jordan. But no matchup floored him more than a game of one-on-one mental chess Jordan and Kobe Bryant staged one night over dinner. For Episode 5 of the Legends of Sport: Restarting the Clock podcast, host Andy Bernstein spoke with Armstrong, now an agent with the Wasserman Agency and rep to Bismack Biyombo, Josh Jackson and JaVale McGee, among others. Excerpted here — and lightly edited for clarity and space — are parts of Bernstein’s conversation with Armstrong, who also dives into how he became an agent and the moment he recognized the contradictions of the term "student-athlete."

You can listen to the entire podcast with Armstrong here or watch here.

Andy Bernstein: How are you preparing for the draft? You can’t go visit guys, and there were no postseason tournaments, so guys weren’t showcased.

BJ Armstrong: It’s been very difficult. We haven’t been able to see the players, we haven’t been able to get in the gym and do the things that we would normally do. By this time, normally we would be playing summer league or have just concluded summer league before we get the players to their cities and try to get them transitioned for training camp. But it’s been a year where everything stopped literally and we’ve been doing a lot of Zoom calls. I’ve become an expert at signing in and signing off of Zoom.

Andy Bernstein: Let's talk about the light bulb that went off in your head that said, “Yeah I want to become a sports agent."

BJ Armstrong: I ask myself all the time, “How did I get here?” I never set out to be an agent. It just kind of happened and I can tell you a quick story. When I went to college, it became very apparent to me this was a business. I got recruited by a number of colleges and I ended up choosing University of Iowa, and as I was on campus as a young kid, 18 or so, it became very apparent to me that this was a business. . . .

Andy Bernstein: Even in college?

BJ Armstrong: Even in the collegiate sports. I would walk into the arenas, I would see signage with names on it, I would see a scoreboard, I would see an arena. We were all required to wear the same shoes, we were required to wear the same practice jerseys. I was just very intrigued how this business worked because it was a business and we were collegiate athletes, student-athletes, but somehow we were playing games in away arenas on Monday night called Big Monday, right, which was on television. We were playing games that really didn’t line up with the student part of what I was doing. I didn’t think it was good or bad.

The thing that brought me here as an agent, if I can try to cut this story down a little bit, is because I had so many questions, I wish I could’ve asked them [while] I was playing. I saw an opportunity to be able to help — or at least be available to these young kids who have questions—because no one ever prepares you for this. There’s nothing in the world that will prepare you for what you’re going to see, other than for you to see it. And then once you got it figured out, you’re probably 32, 33 years old and probably on your way out.

To this day, I don’t think of myself as an agent. I think of myself as just sharing my experience. Here was an opportunity to make yourself available to this next generation. And the basketball part, these kids are incredibly gifted, but the other things I truly just wish I had someone that I could ask these questions to, because I was just literally swimming in the ocean just kind of bumping around, kind of figuring it out. It all worked out for me, but I also know that it could’ve gone the other way.

Andy Bernstein: The last thing I want to talk about is this legendary 2014 dinner that you had with Michael Jordan, who invited this other guy named Kobe Bryant. You were once quoted as saying, they were playing “a virtual game of one-on-one in dissecting each other’s game at dinner.” What was that experience like?

BJ Armstrong: Michael was like, “Someone else is going to meet us here [for dinner].” I was like, “Oh, okay.” I didn’t even think to ask who’s coming and lo and behold, you know, Mr. Bryant, the late Kobe Bryant shows up and it was great. It was great because you saw the respect that they both had for one another, but they couldn’t help but turn on the competitive spirit. I didn’t say a word. I just sat there and watched, where they were just saying how the game would be played if they caught the ball [in a certain spot]. “Well if I catch the ball in the left wing with the live dribble, how would you defend me?”

And the detail that they were going over with these abstract ideas, that’s what really caught my attention. Okay, well how you going to catch the ball? Like, who asks those questions? What’s your pivot foot? What’s the score of the game? How would you defend me if I had it here?

They’re geniuses, and the fact that they didn’t have to actually play a game, that they could actually just play it in their mind, to me was way more impressive than actually watching them play. They were able to mentally play this game and it was one of the most beautiful things I’ve ever seen.

And I remember the conclusion of all of this — this went on for quite some time — they only agreed on one thing: That Michael Jordan had bigger hands than Kobe and that was the deciding factor.

Andy Bernstein: That must’ve killed Kobe because he probably didn’t want to...

BJ Armstrong: Well, he didn’t...The one thing about both of them, they never acknowledged a loss. He just admitted that Michael Jordan had bigger hands.