Freeman arrived on
Jamaica in 1655 as part of
Oliver Cromwell's invasion force, remaining there for the next several years. Freeman obtained a
privateering commission against the Spanish from Lord Windsor,
the Governor of Jamaica, and may have used it to join
Christopher Myngs’ sack of
Santiago de Cuba and
Campeche in 1662-1663. In 1664 he joined with John Morris, Henry Morgan, David Marteen, and
Jacob Fackman to raid the Mexican outposts of
Tabasco and
Villahermosa. Their ships were seized by the Spanish while the buccaneers were ashore. After they captured a few Spanish ships they looted their way through Honduras and Nicaragua, where they captured
Granada with the help of native tribes. Freeman used the proceeds from the raids to purchase a tavern in Port Royal. He later became a Colonel with the Jamaican militia and joined the Jamaican Council alongside future Governor
Hender Molesworth and the recently knighted Henry Morgan. ==See also==