During this time, Milo enlisted the assistance of the pirate Edward Kenway in a variety of manners, including sinking or capturing British and Spanish naval warships, killing particular individuals, and assisting his own trading fleet. Eventually, both the Spanish and the British declared him a wanted man, forcing him to leave the West Indies.
Kenway assisted him one final time, escorting him through four enemy fleets to safety. For all of his efforts, van der Graaff rewarded Kenway with a set of Golden Flintlock Pistols.
- Milo is related to the name Miles, which is Latin word for "soldier"; it has also, however, been suggested to be a derivation of Slavic mil, meaning "grace, gracious." His surname is composed of the Dutch words van, der, and Graaf, meaning "from, of", "the", and "count".