Well aware of the island's burgeoning wealth and repository of supplies, the French pirate Bertrand de Montluc sailed into Funchal harbor with his 11-galleon armada and 1,300 men.
( ( ( Well aware ) ( of ( ( ( ( the ( island 's ) ) ( burgeoning wealth ) ) and ) ( repository ( of ( ( supplies , ) ( the ( French ( pirate ( Bertrand ( de Montluc ) ) ) ) ) ) ) ) ) ) ) ( ( ( sailed ( into ( Funchal harbor ) ) ) ( with ( ( ( his ( 11-galleon armada ) ) and ) ( 1,300 men ) ) ) ) . ) )
(ROOT (S (NP (NP (NNP Well) (NNP aware)) (PP (IN of) (NP (NP (NP (DT the) (NN island) (POS 's)) (VBG burgeoning) (NN wealth)) (CC and) (NP (NP (NN repository)) (PP (IN of) (NP (NP (NNS supplies)) (, ,) (NP (DT the) (JJ French) (JJ pirate) (NNP Bertrand) (FW de) (NNP Montluc)))))))) (VP (VBD sailed) (PP (IN into) (NP (NNP Funchal) (NN harbor))) (PP (IN with) (NP (NP (PRP$ his) (JJ 11-galleon) (NN armada)) (CC and) (NP (CD 1,300) (NNS men))))) (. .)))
Montluc plundered and looted the island, killing many of its residents.
( Montluc ( ( ( ( ( ( plundered and ) looted ) ( the island ) ) , ) ( killing ( many ( of ( its residents ) ) ) ) ) . ) )
(ROOT (S (NP (NNP Montluc)) (VP (VBD plundered) (CC and) (VBD looted) (NP (DT the) (NN island)) (, ,) (S (VP (VBG killing) (NP (NP (JJ many)) (PP (IN of) (NP (PRP$ its) (NNS residents))))))) (. .)))