In 1593, Monson again joined Cumberland, and considering the fidelity which he had always shown to that admiral, the latter seems to have treated him very badly. In the course of their voyage, a dozen Spanish hulks laden with powder were taken, half of which were left to Monson to haul over, while his admiral put to sea with the rest. Monson had with him only about fifty men. What was his surprise towards night to find that Cumberland had released the hulks which he had taken, and that they were crowding on all sail to join their consorts in his charge, with hostile intent, which it would be madness on his part to attempt to frustrate. He barely escaped; when the enemy boarded him on one side of his vessel, he leaped into the long boat on the other side, receiving a wound which remained all his days. Southey certainly puts it mildly when he says, “The conduct of the Earl of Cumberland in this affair admits of no reasonable or satisfactory explanations,” for it looks far more like downright treachery. A couple of years afterwards, the Earl very plainly declared his colours by first inducing him to join him in his voyage, and then superseding him. Monson could not brook this, and returned, after some adventures, to England, where we soon find him with the Earl of Essex, in the expedition to Cadiz. At that most remarkable siege, he was in the thick of the fight ashore with Essex, where he received a shot through his scarf and breeches; another shot took away the handle and pommel of his sword, while he remained uninjured. But his principal services were in connection with the destruction of the fleet, which meant a loss of six or seven millions sterling to Spain. “The King of Spain,” says Monson, “never received so great an overthrow, and so great an indignity at our hands as this; for our attempt was at his own home, in his own ports, that he thought as safe as his chamber, where we took and destroyed his ships of war, burnt and consumed the wealth of his merchants, sacked his city, ransomed his subjects, and entered his country without impeachment.” Monson was knighted for his conduct at this siege.
The abundant “pluck” possessed by Monson is illustrated in the following example. In 1597, on the island expedition, Monson’s ship was separated some distance from the admiral’s squadron, when a fleet of twenty-five sail was noted approaching in the dead of the night. Not being able to distinguish their flag, he determined to reconnoitre for himself, before signalling to the English ships. He approached them in his boat, hailing them in Spanish, and they, replying that they were of that nationality, asked whence he came. He replied that he was of England, and told them that his ship, then in sight, was a royal galleon, and could be easily taken, his object being to make them pursue him, so that he might gradually lead them into the wake of the squadron. All he got for this impudently gallant attempt was a volley of bad language and another of shot.