On Monday night, an invite-only crowd of about 75 blue-suited Wall Street workers and chess devotees hovered around a board on the second floor of the W Hotel in Midtown, awaiting two special guests.

"It's not often you get to see Michael Jordan and LeBron James in the same room," grandmaster Maurice Ashley, the MC for the event, told the throng idling in anticipation of seeing their heroes in action.

In...