Former Cuban leader Fidel Castro, who died Friday at the age of 90, appeared several times on the cover of TIME throughout his life.

Between January 1959 and January 1998, Castro was featured on the cover of TIME nine times, with cover stories detailing his rise to power and his meeting with Pope John Paul II.

“Fidel Castro himself is egotistic, impulsive, immature, disorganized,” TIME wrote in the Jan. 26, 1959 cover story. “A spellbinding romantic, he can talk spontaneously for as much as five hours without strain. He hates desks—behind which he may have to sit to run Cuba. He sleeps irregularly or forgets to sleep, living on euphoria.”

Exactly 39 years later, Castro’s final TIME cover anticipated his visit from the Pope, drawing comparisons between “two giants of the 20th century.”

“The men themselves are fitting adversaries,” TIME wrote. “Both are absolute rulers of their realms. Both are traditionalists and conservatives within their faiths, standing firm against revisionist thinking from within. Each is charismatic and charming, larger than life, with power rooted in his persona. Each plays a dominant role on the world stage, imposing his system of belief upon millions through brilliant intellect and sheer force of will. They are both skilled politicians, adept at tailoring their messages to the moment, yet each always has his eye on the ultimate judgment of history.”

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