What would happen if Spain entered the Second World War, attacked Gibraltar, and invaded Portugal with German support?
Short answerHe expects the Gibraltar attack to fail against a narrow, heavily defended front, Portugal to resist, and Spain itself to become a vulnerable Allied invasion route that Franco's regime might not survive.
NotesGibraltar was an exceptionally difficult land target because attackers would advance over a narrow front exposed to concentrated fire. A major assault might devastate the surrounding area without taking the fortress. Invading Portugal would create another determined opponent with defended borders and a strong commitment to independence. If Spain joined after American entry into the war, the Allies could choose the Iberian Peninsula rather than North Africa or Italy as a southern front. Spain remained deeply divided after its civil war, making Franco's regime unlikely to survive the consequences.