Kap and his wife Mindy were guests of Blackhawks executive vice president Jay Blunk. Bobby Hull, Denis Savard, Tony Esposito and the late Stan Mikita were also in the box, occasionally leaving to sign autographs for nearby fans.
The Blackhawks were playing the Coyotes in Game 6 of the Western Conference quarterfinals, trailing 3-2 in the series. In Game 3, Raffi Torres put a despicable, blindside hit on beloved Hawks winger Marian Hossa, ending his season.
"I remember seeing it and thinking, 'OK, he's done,'" Kaplan said. "I knew he's a big, strong, tough guy, but I thought he was going to be out for [a while]. That was scary."
Despite things looking momentarily grim, the Kap Man knew the Hawks had a very bright future. Around that time, he predicted they'd win four Stanley Cup titles in 10 years on "Sports Talk Live."
"You really look back on the 2010 Blackhawks, that was a sickening amount of talent, man. I mean, crazy amount of talent," he said.
Kap was taking in the game when an unforgettable series of events began to unfold in front of the broadcaster and lifelong Chicago sports fan's eyes.
"My wife and I are literally sitting there in the skybox and my wife hits me and says, 'Did you see who's in the skybox?' And I said, 'Yeah. I was talking to Bobby Hull and those guys earlier.' She's like, 'I'm not talking about that,' and she's hitting me and I'm watching the game. I'm like, 'Hun, I'm trying to watch the game. I don't care who's here.' She's like, 'Oh yes, you do.' I turn around and I'm like, 'Whoa! It's freaking Michael Jordan!'"
Kap turned around and saw the six-time NBA champion walking into his box in a dazzling red Hawks sweater. And not just any Hawks sweater, but a Jonathan Toews sweater.
"That was the amazing thing because if you had said Michael was there, I would have gone, 'Oh, that's really cool,' but the fact that not only was he at the hockey game long since having played for the Bulls, he doesn't have an ownership stake. It's not like he owns the United Center or a portion of it," Kaplan said. "And then to be in not only a jersey, it wasn't a blank jersey on the back, he had a freaking Jonathan Toews jersey on! That was awesome."
Jordan had previously sported a Hawks jersey with his own No. 23 on May 22, 2009 at the UC during another Blackhawks game.
As David approached, Jordan, Mikita and Hull were being positioned for the now iconic photo of the three legends. The Blackhawks asked MJ, who was in another box, to come say hi to Stan and Bobby, and he obliged.
Kaplan was handed a phone to snap a pic of the trio, then Blackhawks team photographer Chase Agnello-Dean captured the moment. Kap noticed the two 1961 Stanley Cup champions' excitement to meet Jordan.
"Both of them were just ecstatic that it was a picture of the three of them together in the box," he said. "Those two Hawks players loved it. The three of them are yucking it up and Michael's like, 'Hey man, I always wanted to hang with you guys."
Then, "His Airness" noticed David. The two had golfed together before, and Kap had coached his older brother Larry in the World Basketball League — for players under 6-foot-five — back in 1988.
"Hey 'D', what's going on?" Jordan said. "You got a Hawks jersey on?" Kaplan said to Jordan. "He's like, 'Absolutely, man. This is awesome out here.' He was great. He was totally into the whole scene. He loved it."
"I remember my wife got to say hi to him," Kaplan recalled. "I said, 'Hey Michael, this is my wife Mindy.' And she sat back down and she's like, 'OK, I'm not starstruck often. That was amazing."
Aside from Air Jordan and the NHL all-time greats in the skybox, two-time American League MVP Frank Thomas shot the puck at intermission, and actor Vince Vaughn had a front row seat for the postseason contest that night.
The Hawks lost to the Coyotes 4-0 and dropped the series 4-2, eliminating them from the 2012 playoffs. Greener pastures awaited the franchise, and that night wouldn't be remembered for a tough finish to a brutal series, but for the time three of the greatest athletes in Chicago sports history got together.
Kaplan recounted sitting in his office one day while he was working for the World Basketball League as director of player personnel, putting a team together for Chicago that he would also coach, and getting an unforgettable phone call. "The secretary goes, 'Kap, could you pick up line one? There's a guy on the phone who says he's Michael Jordan,'" Kap said. "Michael was great, but they hadn't become the Bulls yet. They hadn't won a title. So it wasn't like, 'Oh my god, the pope's on the phone, but it was a big name player. So I pick up the phone and I'm like, 'This is David Kaplan.'
"He goes, 'D', this is Michael Jordan.' And I'm thinking to myself 'is this him or one of my buddies who plays jokes on me?' And the more he talks, he's like, 'Hey, I got a brother, Larry. He's 5'8", but he could jump out of the gym. He's a really good player. If he was bigger, he'd be playing. Would you be open to at least giving him a tryout for your team?'
"He never asked that I put him on the team, but he wanted a tryout. He said, 'If he makes your team and he's good enough, I'm more than willing to help you guys promote your league,' and never charged us a dime.
"Michael Jordan was amazing to deal with. Amazing. So here, I'm coaching his brother, Larry, and I got to know Michael, and the rest is history. That guy became the greatest."