Michael Geare
England and Spain engaged in a privateering war between 1586 though 1603, which is when Geare was active in the West Indies. Geares first voyages was under Sir George Carey. He then worked for John Watts from 1588 through 1591. In 1591 he was made captain of the Little John, which was one of five ships under the command of William Lane.
According to Lane's accounts, Geare was in the fore-front of most of the fighting, gaining for himself a rather large booty plus extra loot by smuggling goods into England. Geare bought a share in the Little John and renamed her the "Michael and John". From 1592 to 1595, Geare had four successful versions in the ship. In 1595, Geare encountered a Spanish warship near Havana. The battle cost the lives of 50 of his crew as well as a pinnace, the Spanish prize he had captured. Geare fled the action in the ''Michael and John'' and was able to recoup some of his losses with the taking of another Spanish prize, after which he returned to England.
In 1596 Geare command of the Neptune and it's pinnace with John Rilesden and Christopher Newport. Towards the end of the year, Geare along with 15 men stole the pinnace plus several more prizes before setting anchor at Jamaica where he joined Sir Anthony Sherley.
Geare, Sherley, and William Parker sailed to Honduras. In 1601, Geare was in command of the warship Archangel and captured 3 valuable ships. Geare was able to get two of the ships back to England but was separated from the third. The crew of the third ship sailed her to Morroco where she was sold.
Geare was instrumental in the capture of two Spanish warships as well as several other ships during 1602 when his ship was part of a three-ship consort led by Christopher Newton.
In 1603, Geare retired to a large home in Stepney, a suburb of London. He was quite wealthy and had been bestowed the honor of knighthood.