The death of Iran’s Supreme Leader Ayatollah Ali Khamenei after a series of U.S. and Israeli attacks over the weekend has left a void at the top of Tehran’s power structure — and taken one of North Korea’s longest-lasting international partners off the board.

Khamenei’s relationship with the DPRK goes back decades, anchored by a 1989 visit to Pyongyang that propelled him to the highest levels of the Iranian regime.

At the time, his visit furthered a budding transactional friendship, but also sent a strong message: North Korea and Iran, driven by mutual enmity toward the U.S., were becoming close