He took part in Henry Jennings' expedition for the sunken 1715 Treasure Fleet off the coast of Florida, and then began sailing with Charles Vane in 1718.

After four months, England and the loyal crewman that had been stranded with him managed to build a boat and sail to a pirate safe haven in Madagascar.

[9] England took part in Henry Jennings' assault on the Spanish salvage camp at Palma de Ayz, Florida, stealing £87,000 in gold and silver.

Vane's sloop, the Lark, was captured by the Royal Navy, but England and the rest of the crew were released to induce the other pirates of Nassau to accept the King's pardon.

England decided not to accept the pardon along with Vane and a few others, and after the arrival of Woodes Rogers, they set sail for the coast of Africa.

Howell said he would rather die than become a pirate, however, England refused to kill him and instead gave command of the captured ship to Davis.

After looting two additional ships, England and the crew decided to make port in a small African town.

By 1720, England had reached the Indian Ocean, where he met with fellow pirate Captain Oliver la Buse.

Finally Macrae, who was injured, tired, and hungry, went aboard England's consort the Victory, hoping for mercy, and surrendered to the pirates.

England then captured a small English ship near Cochin, the drunk captain reporting a false rumour that Macrae was preparing a fleet to chase the pirates.

[9] The new captain – a former member of the Fancy crew named Jasper Seator – marooned England and three others on the coast of Mauritius, before taking Cassandra and Victory north in the hunt for more prizes.

[16] After about four months, the men built a small boat and managed to sail to the pirate haven of St. Augustine's Bay in Madagascar.

According to Captain Charles Johnson, He had a great deal of good Nature, and did not want for Courage ; he was not avaritious, and always averse to the ill Usage of Prisoners received : He would have been contented with moderate Plunder, and less mischievous Pranks, could his Companions have been brought to the same Temper, but he was generally over-rul'd, and as he was engaged in that abominable Society, he was obliged to be a Partner in all their vile Actions.