he then took part in an expedition to the spanish main in 1595 under the command of francis drake. after defeat at san juan in december, baskerville became second in command after the death of john hawkins. in january 1596 an attempt to cross the isthmus of panama from nombre de dios in order to seize the silver rich port of portobelo, colón also ended in failure. ravaged with dysentery and other diseases baskerville bravely led his troops over thirty miles before heading back. drake would die of the former and the expedition was forced to retreat back to england all the while harassed by the spanish.