SEOUL—In 1989, South Korean authorities charged a young political activist named Im Jong-seok with colluding with the enemy after he helped a fellow student make a secret, illegal trip to North Korea to meet the country’s then-dictator Kim Il Sung—a propaganda coup at the time for Pyongyang.
Nearly three decades later, Mr. Im, now chief of staff to South Korea’s president, is playing a leading role in Seoul’s diplomatic outreach to Pyongyang, helping set the stage for meetings between the two Koreas’ leaders Friday and between...