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 tried to win the entire shooting match by taking a long-shot at a winner-takes-all target.
( He ( ( tried ( to ( ( win ( the ( entire ( shooting match ) ) ) ) ( by ( ( taking ( a long-shot ) ) ( at ( a ( winner-takes-all target ) ) ) ) ) ) ) ) . ) )
(ROOT (S (NP (PRP He)) (VP (VBD tried) (S (VP (TO to) (VP (VB win) (NP (DT the) (JJ entire) (NN shooting) (NN match)) (PP (IN by) (S (VP (VBG taking) (NP (DT a) (NN long-shot)) (PP (IN at) (NP (DT a) (JJ winner-takes-all) (NN target)))))))))) (. .)))