While he could have enjoyed the comforts of life as an important personality in Cuba, Che chose the hard road of a revolutionary with the support of his friend Fidel. He took part in two other campaigns in Congo and Bolivia which were both unsuccessful. Congo was a fiasco. Bolivia cost him his life.
Che Guevara at the funeral for the victims of the La Coubre explosion by Alberto Korda. (Popularized cropped version of Guerrillero Heroico) Wikimedia Commons
One major reason for the failure of the latter campaigns was the attempt to repeat the Cuban experience in those countries. The modus operandi of the guerrillas was to enter the relatively inaccessible hinterland and slowly gather local support. It was hoped that a small but well trained guerrilla force would act as the vanguard of the revolution. This was what they employed in Cuba and was successful there with the aid of some advantages the guerrillas had. Che Guevara remarked in his book "Guerrilla Warfare" that "[I]t is not necessary to wait until all conditions for making revolution exist; the insurrection can create them."
While this may be true, it does not assure that an armed group championing the cause of the people will always attract popular support. This is a fact that Che Guevara overlooked and ultimately payed the prize for.
In Cuba, after some initial blunders and misfortunes, the guerrillas found their way and moved on. Initially, the local population was vary and skeptical about the guerrillas but slowly they began to support them. Of course, Fidel's men were helped by the New York Times reporter Herbert Matthews who interviewed the rebel leader and published three articles which turned the guerrillas into heroes. With the passage of time, local population increasingly supported the rebel forces which started their march towards Havana.
However, both in the Congo and in Bolivia, Che Guevara could not garner enough popular support despite almost all other condition for a successful rebellion was more or less evident on the ground. The people felt that the guerrillas were foreign to them, and as for the Cubans led by Che, they were. Many could not understand the internationalism of the Cubans involved. The Cuban revolution was led by a Cuban and while Guevara was not a native Cuban he was not the overall commander of the revolutionary forces either. He was just taking part, albeit a big part, in the war. In contrast, he was leading a campaign in Bolivia. The fact that a Cuban led the movement in Bolivia did not help the matters.
This was perhaps the most vital factor which determined the outcome of the fiasco of Congo and the disaster of Bolivia. This precluded the possibility of long lasting unity among the guerrillas in these campaigns. The Congolese rebels were a poorly led, undisciplined crowd who wasted the money collected and given to them by Cuba and other countries on more worldly pleasures. More importantly, they resented some outsider coming and telling them what they should and should not be doing.
In Bolivia also this disunity and resentment was a key factor in determining the outcome. Che Guevara's "Bolivian Diary" describes the first skirmish they had with Bolivian soldiers which claimed a life of a Cuban. Che deemed it necessary to point out that it was Cuban blood which was first shed in the Bolivian struggle. The avowed internationalist took this decision to cultivate comradeship between the two groups but it hardly succeeded. The Communist Party of Bolivia also did not extend its support to Che Guevara which was another blow. Che once described the party in his "Bolivian Diary" as a distrustful, disloyal and stupid entity. The dogmatist he was, Guevara did not pull out of the campaign when it was obvious that things were going horribly wrong. One reason may have been the fact that he had been completely cut off from Havana and therefore, isolated and stranded in Bolivia. If communications were open with Havana, Castro might have asked him to pull out and he might have heeded. Once he had heeded such warning in Congo and saved himself to fight another battle.
The United States aided Bolivia in the battle against the guerrillas, which added to the difficulties of the latter. Despite this, a united band of guerrillas might have given a better fight. In almost all skirmishes, the Bolivian Army suffered worse. But, with the passage of time, numerical superiority and foreign aid helped the Bolivian forces. Also, as the guerrillas were led by a Cuban, the authorities could project the campaign as a foreign encroachment of Bolivian territory. Forced out of their bases and later separated to two bands, the guerrillas wandered in the inhospitable terrain while engaging the Army. As the rebels had no popular support to speak of, entering villages was also risky. They were ultimately decimated, Che Guevara's execution being one of the final acts. Only a handful survived to tell the tale.
The dogmatic internationalist he was, Ernesto 'Che' Guevara most probably failed to understand the inherent nationalism of many others around him, which ultimately cost him his life.
References
1. Rooney, D. Guerrilla: Insurgents, Patriots and Terrorists from Sun Tzu to Bin Laden, Brassey's, London (2004)
2. Guevara, Ernesto (Che), Guerrilla Warfare (1961)
3. Guevara, Ernesto (Che), Bolivian Diary (1966-67)