Then he shoots his bolt and wad by taking a long shot at some one-shot deal that will win him the whole shooting match.
( Then ( he ( ( ( shoots ( his ( ( bolt and ) wad ) ) ) ( by ( ( taking ( a ( long shot ) ) ) ( at ( ( some ( one-shot deal ) ) ( that ( will ( ( win him ) ( the ( whole ( shooting match ) ) ) ) ) ) ) ) ) ) ) . ) ) )
(ROOT (S (RB Then) (NP (PRP he)) (VP (VBZ shoots) (NP (PRP$ his) (NN bolt) (CC and) (NN wad)) (PP (IN by) (S (VP (VBG taking) (NP (DT a) (JJ long) (NN shot)) (PP (IN at) (NP (NP (DT some) (JJ one-shot) (NN deal)) (SBAR (WHNP (WDT that)) (S (VP (MD will) (VP (VB win) (NP (PRP him)) (NP (DT the) (JJ whole) (NN shooting) (NN match)))))))))))) (. .)))
He didn't attempt to hit any of the targets. 
( He ( ( ( did n't ) ( attempt ( to ( hit ( any ( of ( the targets ) ) ) ) ) ) ) . ) )
(ROOT (S (NP (PRP He)) (VP (VBD did) (RB n't) (VP (VB attempt) (S (VP (TO to) (VP (VB hit) (NP (NP (DT any)) (PP (IN of) (NP (DT the) (NNS targets))))))))) (. .)))