Three sieges of San Juan: Drake, Cumberland, and the Dutch (1595-1625)

On November 22, 1595, the English privateer Sir Francis Drake entered the bay of San Juan with 27 ships and some 2,500 soldiers, intending to sack the settlement and claim its treasure. Spanish forces entrenched in the forts repelled the attack before it could take hold, sending Drake's fleet back empty-handed.

Cumberland's assault a few years later was different, and far more damaging to the city. On June 15, 1598, an English force of some 20 ships and 1,700 men, under Sir George Clifford, third Earl of Cumberland, landed troops east of the city, fought their way across the San Antonio bridge under heavy Spanish fire, and overwhelmed Castillo San Felipe del Morro, taking the city of San Juan itself.

Cumberland's forces held the city some 65 days before an outbreak of dysentery forced them to withdraw, but not before sacking and burning it. This remains, according to Wikipedia, the only attack that ever broke and captured El Morro outright. Spain rebuilt the following year, sending soldiers, cannons, and a new governor, Alonso de Mercado, to restore San Juan.

A third assault came from an entirely different direction. On September 25, 1625, a Dutch expedition under Boudewijn Hendricksz, also known as Balduino Enrico, attacked and besieged San Juan for about two months. Spanish forces under Governor Juan de Haro held Fort San Felipe del Morro and repelled the assault, and the Dutch never managed to capture the city.

Taken together, these repeated attempts, and Cumberland's brief but real success, explain why Spain kept expanding San Juan's fortifications over the following two centuries, a reinforcement covered in the lessons that follow.

Sources: Historia de Puerto Rico; Batalla de San Juan (1598); Batalla de San Juan (1625); Francis Drake; George Clifford, tercer conde de Cumberland. Freeze 2026-08-22.